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[ CAS No. 122-00-9 ] {[proInfo.proName]}

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Chemical Structure| 122-00-9
Chemical Structure| 122-00-9
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Product Citations

Product Citations

Siriboe, Mary G ; Vargas, David A ; Fasan, Rudi DOI: PubMed ID:

Abstract: Chiral cyclopropanols are highly desirable building blocks for medicinal chemistry, but the stereoselective synthesis of these molecules remains challenging. Here, a novel strategy is reported for the diastereo- and enantioselective synthesis of cyclopropanol derivatives via the biocatalytic asymmetric cyclopropanation of vinyl esters with ethyl diazoacetate (EDA). A dehaloperoxidase enzyme from Amphitrite ornata was repurposed to catalyze this challenging cyclopropanation reaction, and its activity and stereoselectivity were optimized via protein engineering. Using this system, a broad range of electron-deficient vinyl esters were efficiently converted to the desired cyclopropanation products with up to 99.5:0.5 diastereomeric and enantiomeric ratios. In addition, the engineered dehaloperoxidase-based biocatalyst is able to catalyze a variety of other abiological carbene transfer reactions, including N?H/S?H carbene insertion with EDA as well as cyclopropanation with diazoacetonitrile, thus adding to the multifunctionality of this enzyme and defining it as a valuable new scaffold for the development of novel carbene transferases.

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Product Details of [ 122-00-9 ]

CAS No. :122-00-9 MDL No. :MFCD00008751
Formula : C9H10O Boiling Point : -
Linear Structure Formula :(CH3)C6H4COCH3 InChI Key :GNKZMNRKLCTJAY-UHFFFAOYSA-N
M.W : 134.18 Pubchem ID :8500
Synonyms :
Chemical Name :1-(p-Tolyl)ethanone

Calculated chemistry of [ 122-00-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.6
TPSA : 17.07 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.569 mg/ml ; 0.00424 mol/l
Class : Soluble
Log S (Ali) : -2.09
Solubility : 1.09 mg/ml ; 0.00815 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.09
Solubility : 0.11 mg/ml ; 0.000818 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 122-00-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H227-H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 122-00-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 122-00-9 ]

[ 122-00-9 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 4903-09-7 ]
  • [ 122-00-9 ]
  • 3-chloro-4-methoxy-4'-methyl-<i>trans</i>-chalcone [ No CAS ]
  • 2
  • [ 383-63-1 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
100% With sodium; In ethanol; at 20℃; for 3.2h; A solution of sodium (0.12 g, 5.2 mmol, 1.4 eq.) was dissolved in absolute ethanol (3.9 mL) followed by the dropwise addition of ethyl trifluoroacetate (4, 0.5 m L, 4.1 mmol, 1.1 eq.). Thereafter 4'-methylacetophenone (3, 0.50 ml, 3.8 mmol, 1.0 eq) in absolute ethanol (1.4 ml) was added dropwise over 15 minutes. The reaction mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo and the solid obtained suspended in hexane (15 ml) with vigorous stirring followed by vacuum filtration and washing with hexane (2 x 2 ml) to obtain a cream-coloured solid (0.86 g, 3.7mmol, 100%). /?/ = 0.23 (25 % EtOAc/hexane). 1H NMR (400 MHz c/e-DMSO) 7.69 (d, 2H, J 7.69, Ar-H); 7.19 (d, 2H, J 7.18, Ar-H); 5.92 (s, 1H, COCH2CO); 2.31 (s, 3H, CH3). 13C N MR (100 MHz d6-DMSO) 185.62, 169.27*, 168.99*, 168.71*, 168.44*, 139.89, 138.96, 128.70, 126.66, 123.78?, 120.88?, 117.98?, 115.07?, 86.84, 20.91. 19F NMR (377 MHz, c/6-DMSO) -74.42. *?Signals exhibit splitting due to coupling with fluorine.
99.08% With potassium carbonate; In isopropyl alcohol; acetonitrile; at 40℃; for 24h; To a 500 mL one-necked flask was added 200 mL of acetonitrile-isopropanol (1: 1), 200 mmol (26.8 mL) of p-methylacetophenone (I), 600 mmol (72 mL) of ethyl trifluoroacetate (II), 360 mmol Diameter of 600nm potassium carbonate, 40 C reaction 24h Filtration recovery of potassium carbonate and potassium bicarbonate, high temperature treatment can be reused. Mother liquor distillation, recovery of solvent and unreacted raw materials for the next reaction. Add equal volume of water to the distillation residue, adjust the pH to 6 with 10% hydrochloric acid, extract with ethyl acetate 4 times, 70mL each time, combine the organic phase, concentrate and freeze to obtain the pale yellow solid product (III) 45.6 G, the yield was 99.08%.
99.8% With tert-butyl methyl ether; sodium ethanolate; In ethanol; at 25℃; for 24h;Inert atmosphere; Under nitrogen protection, Separately add methyl tert-butyl ether (3.0 L) and 20 wt% sodium ethoxide in ethanol solution (3.55 kg, 10.43 mol), replacing nitrogen 3 times. Control temperature does not exceed 25±5C, mechanical stirring, Ethyl trifluoroacetate (3) was added in batches (1.27kg, 8.94mol) and p-methylacetophenone (4) (1.0 kg, 7.45 mol). Under nitrogen protection, The control reaction temperature is 25±5C, mechanical stirring for 24h. TLC detected that the disappearance of the raw materials was completed (developer: petroleum ether/ethyl acetate, volume ratio 1/1). Stop the reaction, the reaction solution was added 5wt% hydrochloric acid solution (6.5L) to adjust the pH of 7.0 ~ 8.0, let stand for 15min, Separate the layers and collect the organic phase. The aqueous phase was extracted with ethyl acetate (2.0 L); the organic phases were combined and purified water (8 L) and saturated water were added in order. Wash with brine (5.0 L), dry the organic phase over anhydrous sodium sulfate (1.0 kg), suction filter, and rinse the filter cake with a small amount of ethyl acetate. Concentrate to dryness under reduced pressure at 45 C to give compound 1 as a red-brown oil. Yield 99.8%, HPLC purity 98.4%
94% With sodium methylate; In methanol; for 24h;Heating / reflux; Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried overMgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% Following the disclosure provided in U. S. Patent No. 5,760, 068,4'- Methylacetophenone (5. 26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5. 5 mL (46.2 mmbl) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% Step 1: Preparation of 1- (4-METHYLPHENYL)-4, 4,4- trifluorobutane-1, 3-dione. [000201] Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 MMOL) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 MMOL) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 MMOL) ETHYL TRIFLUOROACETATE was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MGS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 MMOL) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 MMOL) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MGS04, FILTERED and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% 4'-methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94% 4'-methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MgS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
94.8% With sodium methylate; In toluene; at 20 - 30℃; for 5h; In a 1000 ml reaction flask, add 500.0 g of toluene and 187.9 g (1.40 mol)P-methylacetophenone, 94.1 g of sodium methoxide (1.68 mol), slowly dropwise add 238.8 g of ethyl trifluoroacetate (1.54 mol), and keep it at 20-30 C. After the dropwise addition, continue to react for 5 hours. A good 5N hydrochloric acid solution is used to adjust the pH to 2, and then washed twice with 500 g of purified water; the washed organic phase is slowly cooled to -10 C to -5 C, crystallized for 2 hours, and filtered and dried to obtain 305.5 g of light yellow. Solid, molar yield 94.8%, purity 99.8%.
89% (1) To a 100 mL round bottom flask was added 14.9 mmol of 4-methylacetophenone (Compound 3b)Dry THF 30 mL,Cooling to -5 ~ 0 ,NaH 0.715 g (29.8 mmol) was added portionwise under nitrogen,Stir at this temperature for 30 min,Was added 3.175 g (22.4 mmol) of ethyl trifluoroacetate,The reaction was stirred at room temperature for 6 h,The solvent was distilled off under reduced pressure, diluted with ice water,The pH of the solution was adjusted to 6 with 1 mol / L HCl,The organic layer was washed with 5 mL of water and dried over anhydrous magnesium sulfate. The solvent was dried and the concentrated product was dried. The organic layer was washed with 5 mL of water,To give compound 4b (4,4,4-trifluoro-1- (4-methylphenyl) -1,3-butanedione) in 89% yield;
87% 25% sodium methoxide in methanol (51.3 ml, 223.5 mmol) and ethyl trifluoroacetate (24.4 ml, 204.9 mmol) were dissolved in 110 mL methyl tert-butyl ether under N2, at room temperature. 4'-methyl acetophenone (25.0 ml, 186.3 mmol) was added and stirred at room temperature overnight. The reaction was washed with 3M HC1 and dried over magnesium sulfate. The solution was then evaporated and the resulting oil dried under vacuum overnight. The resulting light orange crystalline solid was washed with cold isooctane and dried under vacuum to yield an off white crystalline solid (37.3 g, 87% yield). LC tr=3.49 minutes (C- 18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C).
87.3% Will p-methyl acetophenone (0.67g, 5mmol)Soluble in 20mL dry THF,NaH (0.24 g, 10 mmol) was added at 0C.Stir for 10 min.Adding ethyl trifluoroacetate under N2 protection(0.9 mL, 7.5 mmol) into the reaction solution,The drop was transferred to room temperature and the reaction was continued for 12 h.After the reaction was completed, it was quenched with saturated aqueous sodium bicarbonate (50 mL).And extracted with ethyl acetate (50 mL x 3).Combine the organic phase,Dry, concentrate.The crude product was purified by column chromatography to give 1 g of a yellow solid.Yield 87.3%.
86% With sodium; In methanol; for 24h;Reflux; Add 4.5 g of metallic sodium to 70 ml of anhydrous methanol.After the reaction is completed, it is cooled to room temperature.Slowly add p-methylacetophenone 13.5g (100mmol)And ethyl trifluoroacetate 17g (120mmol), after the addition is completed,The mixture was heated to reflux for 24 hours and concentrated to a yellow viscous liquid.Add 2mol/L hydrochloric acid to adjust the pH to 2~3, extract with ethyl acetate.Drying with magnesium sulfate,The solvent was evaporated to give a yellow oil, 1-p-tolyl-4,4,4-trifluorobutane-1,3dione, 20 g, yield 86%.
85% Intermediate 10: 4,4,4-trifluoro-1-(p-tolyl)butane-1,3-dione To a solution of MeONa prepared from sodium (1.919 g, 83.0 mmol) and methanol (60 mL) was added ethyl 2,2,2-trifluoroacetate (ALDRICH, 8.19 ml_, 54.8 mmol) and the reaction was stirred at rt 30 min. Then 1-(p-tolyl)ethanone (ALDRICH, 6.97 mL, 52.2 mmol) was added, the reaction mixture was heated at 60C overnight. The reaction was checked by LCMS and the end of the reaction was observed. The reaction mixture was concentrated under vacuum and partitioned between sodium carbonate (10%) 25 mL and DCM (25 mL), the organic layer was separated, dried over Na2S04, filtered and concentrated under vacuum to afford a brown solid (10.2 g, 44.3 mmol, 85%). 1H NMR (400 MHz, CDCI3) delta ppm: 7.85 (d, 2H), 7.30 (d, 2H), 6.56 (s, 1 H), 2.45 (s, 3H).
85% To a solution of MeONa prepared from sodium (1.919 g, 83.0 mmol) and methanol (60 mL) was added ethyl 2,2,2-trifluoroacetate (ALDRICH, 8.19 mL, 54.8 mmol) and the reaction was stirred at rt 30 min. Then 1-(p-tolyl)ethanone (ALDRICH, 6.97 mL, 52.2 mmol) was added, the reaction mixture was heated at 60 C. overnight. The reaction was checked by LCMS and the end of the reaction was observed. The reaction mixture was concentrated under vacuum and partitioned between sodium carbonate (10%) 25 mL and DCM (25 mL), the organic layer was separated, dried over Na2SO4, filtered and concentrated under vacuum to afford a brown solid (10.2 g, 44.3 mmol, 85%). 1H NMR (400 MHz, CDCl3) delta ppm: 7.85 (d, 2H), 7.30 (d, 2H), 6.56 (s, 1H), 2.45 (s, 3H).
8.47 g (94%) With hydrogenchloride; In methanol; Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was.stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
8.47 g (94%) With hydrogenchloride; In methanol; Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
8.47 g (94%) With hydrogenchloride; In methanol; Step 1 Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
With hydrogenchloride; sodium methylate; In methanol; Step a 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione 4'-Methylacetophenone was dissolved in methanol (25 ml) under nitrogen atmosphere. To the stirred solution was added 25% sodium methoxide in methanol (12 ml). The reaction mixture was stirred for 5 minutes and ethyltrifluoroacetate (5.5 ml) was added. After refluxing under nitrogen atmosphere for 24 hours the mixture was cooled to room temperature and concentrated. 10% hydrochloric acid (100 ml) was added. The mixture was extracted with ethyl acetate (4*75 ml). The combined organic layer was dried over MgSO4, filtered and concentrated. The product was obtained as an oily residue.
8.47 g (94%) With hydrogenchloride; In methanol; Step 1 Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
8.47 g (94%) With hydrogenchloride; In methanol; Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
8.47 g (94%) With hydrogenchloride; In methanol; Step 1: Preparation of 1-(4-methylphenyl)-4,4,4-trifluorobutane-1,3-dione. Following the disclosure provided in U.S. Pat. No. 5,760,068, 4'-Methylacetophenone (5.26 g, 39.2 mmol) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 mmol) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 mmol) ethyl trifluoroacetate was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCl was added and the mixture extracted with 4*75 mL ethyl acetate. The extracts were dried over MgSO4, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.
With sodium methylate; In methanol; toluene; at 25 - 60℃; Stage-1:Preparation of l-(4-methylphenyl)-4,4,4-trifluorobutane-l,3-dione (IV)4-Methylacetophenone (50 g, 0.373 mol) was dissolved in toluene (250 ml) and 30% methanolic sodium methoxide solution (80.6 g, 0.447 mol), followed by 1- ethyltrifluoro acetate (63.58 g, 0.447 mol) were added at 25-3O0C. Temperature of the reaction mass was raised to 55-600C and stirred ~ 4 hr to complete the reaction. The reaction mass was cooled to 20-250C and washed with 10% aqueous hydrochloric acid (200 ml). The layers were separated and concentrated the organic layer at 50-550C under reduced pressure to produce 80 g of l-(4-methylphenyl)-4,4,4-trifluoiObutane- 1,3-dione (IV) as an oily mass.
General procedure: Substituted acetophenone 1 (149 mmol) was dissolved in dry THF (300 mL) under nitrogen atmosphere and NaH (7.15 g, 298 mmol) was added in portions maintaining the temperature between -5 and 0 C. After stirring at this temperature for 30 min, ethyl trifluoroacetate (31.75 g, 224 mmol) was added and the reaction mixture was allowed to stir at room temperature for 6 h. The reaction mixture was evaporated, added with ice-water, acidified with HCl (1 N) to pH 6, and extracted with EtOAc (3 × 100 mL). The combined organic layer was washed with water (50 mL), dried over MgSO4, and concentrated. The solid residue was washed with hexane and dried under high vacuum to provide a solid mass, which was re-dissolved in CH2Cl2, and dried under high vacuum to give a white solid diketone 2 in 92 +/- 2% (n = 3) yield, Rf = 0.22-0.25 (25% EtOAc/Hexanes).
General procedure: Step a. To a suspension of ethyl trifluoroacetate (850 mg, 6 mmol, 1.2 equiv) and NaH (150 mg, 6.25 mmol, 1.25 equiv) in anhydrous THF, individual ketone substrates (5 mmol, 1 equiv) in anhydrous THF were slowly added at 25 C. The resulting mixture was stirred for 5 h, concentrated, diluted with ethyl acetate, washed, in tandem, with water, 1 N HCl and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc-hexane, 1:4) to afford pure 1,3-diketone in fair to good yields.
With sodium methylate; In methanol; for 2h;Reflux; General procedure: Referring to Scheme 1, to the appropriate acetophenone derivative (0.05 mol) and ethyltrifluoroacetate (0.075 mol) in methanol (20 mL), sodium methoxide solution (0.1 mol of Na + 15 mL ofCH3OH) was added dropwise at room temperature, and the mixture was refluxed for 2 h. After themethanol was evaporated under vacuum, the residue was dissolved in ethyl acetate (50 mL), washedwith 5% HCl (25 mL) and water (25 mL), and dried over sodium sulfate. After the solvent wasevaporated under vacuum, the corresponding compound II was obtained.
63.5 g With sodium; In ethanol; toluene; at 100℃; for 4h; Sodium metal (6.9g, 0.3mol) and toluene (150 mL) made of an off-white suspension, was added absolute ethanol (20 mL), at 65 C for 1 hour, cooled to room temperature. Added p-methylacetophenone (40.2g, 0.3mmol) and ethyl trifluoroacetate (60mL, 0.6mmol), was slowly warmed to 100 C for 4 hours. Toluene was evaporated, and the residue was added to a mixture of ice and glacial acetic acid (containing 33% glacial acetic acid), and extracted four times with ethyl acetate. The combined extracts were washed with water, dried over anhydrous sodium sulfate, the solvent was evaporated to obtain a brown solid 63.5g.
With sodium methylate; In methanol; isopropyl alcohol; at 50℃; for 4h; In a 250 mL three-necked glass flask, p-methylacetophenone (10 g, 0.075 mol) and ethyl trifluoroacetate(13.7 g, 0.096 mol), 18.2 g of sodium methoxide in methanol (25% concentration) and 20 mL of isopropanol were added and the temperature was raised to 50 C, after holding for 4 h, the temporary solution for the reaction a.
A solution of 27 p-methylacetophenone (0.67g, 5mmol) in dry 28 THF (20mL) was added dropwise to 29 NaH (0.24g, 10mmol) in dry THF (50mL) under nitrogen atomosphere and the mixture was stirred for 1h at 0C. Then a solution of 30 ethyl trifluoroacetate (0.9mL, 7.5mmol) in dry THF (10mL) was added dropwise. The mixture was warmed to room temperature for 12h. The reaction was quenched with saturation NaHCO3 and extracted with ethyl acetate (50mL×3). The combined organic extracts were washed with brine (50mL), dried with Na2SO4 and evaporated. Finally, the resulting residue was purified by column chromatography on silica gel as indicated to give 6a as canary yellow solid. (0015) To a solution of 6a (0.46g, 2mmol) in 31 ethyl alcohol (50mL) was added 32 4-hydrazinyl-N-hydroxybenzamide hydrochloride (0.53g, 2.6mmol). Then the temperature was raised to 70C for 5h. The mixture solution was concentrated to dryness, added 33 water (50mL) and extracted with ethyl acetate (30mL×3). The combined organic extracts were washed with brine (30mL), dried with Na2SO4 and concentrated. Finally, the resulting residue was purified by column chromatography on silica gel as indicated to give 7 as white solid. (0016) To a solution of 7 (0.36g, 1mmol) in 34 methyl alcohol (30mL) were added 1M aqueous solution of 35 NaOH (3mL) and 36 NH2OH (50wt% in water, 3mL) dropwise successively at 0C. The reaction was warmed to room temperature for 3h. The mixture solution was concentrated to dryness, and the obtained solid was dissolved in water. The pH was adjusted to 7 with 1M aqueous solution of 37 HCl. The resulting precipitate was filtered to give 38 8 as white solid. Yield: 63.2%. Mp: 104.5-105.9C. ESI-MS: m/z, 360.3 [M-H]-. 1H NMR (600MHz, DMSO-d6) delta: 11.33 (s, 1H), 9.13 (s, 1H), 7.80 (d, J=8.6 Hz, 2H), 7.42 (d, J=8.6 Hz, 2H), 7.21-7.18 (m, 4H), 7.17 (s, 1H), 2.30 (s, 3H). 13C NMR (151MHz, DMSO) delta: 145.19, 140.87, 139.03, 132.90, 129.56, 129.43, 128.77, 128.00, 126.86, 125.60, 125.54, 105.91, 20.86. HRMS (ESI+) m/z calcd for C18H14F3N3O2 [M-H]- 360.1038, found: 360.1047.
Following the disclosure provided in U. S. Patent No. 5,760, 068, 4'-Methylacetophenone (5.26 g, 39.2 MMOL) was dissolved in 25 mL of methanol under argon and 12 mL (52.5 MMOL) sodium methoxide in methanol (25%) was added. The mixture was stirred for 5 minutes and 5.5 mL (46.2 MMOL) ethyl TRIFLUOROACETATE was added. After refluxing for 24 hours, the mixture was cooled to room temperature and concentrated. 100 mL 10% HCI was added and the mixture extracted with 4 x 75 mL ethyl acetate. The extracts were dried over MGS04, filtered and concentrated to afford 8.47 g (94%) of a brown oil which was carried on without further purification.

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  • 3
  • [ 92-55-7 ]
  • [ 122-00-9 ]
  • [ 32023-50-0 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; acetic acid; at 20℃; General procedure: To a well-stirred solution of 5-nitro-2-(furyl/thienyl)methyldiacetate 1 (5 mmol) in 20 cm3 glacial acetic acid, substitutedacetophenone 2 (5 mmol) and 0.5 cm3 of conc. H2SO4 were added. The reaction mixture was stirred for 1 h andkept aside at room temperature. The propenone crystals 3formed were collected by filtration and washed with ethanol.The crude product 3 (5 mmol) was dissolved in 20 cm3glacial acetic acid by heating. 30% v/v bromine solution wasadded drop by drop until bromination was complete. Thereaction mixture was stirred for 2 h and kept aside overnight.The alpha,beta-dibromochalcones 6 formed were filtered, washedwith ethanol, and recrystallized from glacial acetic acid. Thedibromochalcone 4 (5 mmol) was taken in a round-bottomedflask and 25 cm3 of dry benzene was added. To this, triethylamine(6 mmol) was added and the flask was closedwith a lid. The mixture was stirred for 4 h and the separatedtriethylammonium hydrobromide filtered off. The filtratewas roto-evaporated and the solid separated was collectedby filtration and further purified by recrystallization fromethanol. The compounds were characterized by reference totheir melting point [34, 35] and the data are given in ESI.
  • 4
  • [ 7647-01-0 ]
  • [ 124-41-4 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
In methanol; PART B Preparation of 1-(4-Methylphenyl)4,4,4-Trifluorobutane-1,3-Dione 125 gms (0.93 mol) of p-Methylacetophenone was dissolved in 250 ml Methanol (anhydrous) and 270 ml of Sodium Methoxide (25percent in methanol) was added slowly maintaining the temperature below 30 deg C. The reaction mixture was further diluted with 250 ml Methanol and 128 ml of Ethyltrifluoroacetate(1.0 mol) was added in 4 lots with a in-between stirring period of 5 hours. The reaction was stirred at 20 -30 deg C for 16 hours. The reaction mixture was concentrated under vacuum below 40 deg C to 50percent and then poured over mixture of 150 ml concentrated Hydrochloric acid and 200 gms ice. The mixture was stirred below 5 deg C for 2 hours and filtered. the product was washed with water till neutral pH and suck dried under vacuum 0.25 gms of p-Methylacetophenone was recovered from the filtrate. The 1-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione was dried under vacuum to give III gms off white crystalline product.(65percent) This was further recrystallized from Isopropanol to give 90 gms of white crystals. M.pt 50-52 deg C. IR KBr cm-1 1064 (C-C), 1147 (C=O), 1199 (CF3), 1458 (C-H), 1608 (aromatic C=O)
  • 5
  • [ 2797-51-5 ]
  • [ 7732-18-5 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride; lithium hexamethyldisilazane; In acetonitrile; PREPARATIVE EXAMPLE 1 4,4,4-Trifluoro-1-(4-methylphenyl)-butane-1,3-dione Under nitrogen, to a 100 L three-necked round bottom flask equipped with a mechanical stirrer, a nitrogen inlet and a thermocouple charge lithium hexamethyldisilazide (LHMDS) and tetrahydrofuran (THF) (25.0 l, KF=80) at -60° C. Add 4-methylacetophenone over 30 min. Age the mixture at -60° C. for 30 min. Add 2,2,2-trifluroroethyl trifluoroacetate over 30 min, maintaining the temperature at lower than -50° C. during the additions. Age the mixture for 20 hrs at ambient temperature. Allow the mixture to come to 0° C. Add 3N HCl slowly so that the temperature is maintained at less than 20° C. Age the mixture for 30 min. Separate in the separatory cylinder (100 L) give the THF layer. Concentrate and switch solvents to acetonitrile (ACN). Add ACN to a volume of 12 L. Cool the solution to -10° C. Add H2 O (8.0 L). Slowly add additional H2 O (45.0 L). Age the mixture at ambient temperature for 3 hrs. Isolate the solid by filtration via an insulated sintered funnel. Rinse the wet cake with H2 O (20.0 L). Dry under reduced pressure to afford 3.68 kg (approx) of the product at 86percent yield.
  • 6
  • [ 122-00-9 ]
  • [ 76-05-1 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
100% To a 0°C coldsolution of 1.01 g (7.53mmol) 4?-methylacetophenon in 20 mL abs. THF 0.36 g (8.94 mmol) sodium hydride (60percent in mineraloil) were added portionwise under argon. After stirring for 30 mintrifluoroacetic acid (1.27 g, 8.94 mmol) was added and stirring was continuedfor 5 h at room temperature. The mixture was added to 50 mL acidified ice-waterand extracted twice with ethyl acetate (50 mL). The combined organic phaseswere washed with water (3 x 50 mL), dried over Na2SO4,filtrated and concentrated in vacuum affording 1.74 g (quant.) brownish oilthat was used in the next step without further purification. ModifiedADDIN EN.CITEAhlstroem2007171717MarieM. AhlstroemMarianneRidderstroemIsmael ZamoraKristinaLuthmanCYP2C9Structure-Metabolism Relationships: Optimizing the Metabolic Stability ofCOX-2InhibitorsJ. Med.Chem.J.Med. Chem.4444-4452502007[1]. 1H-NMR(250 MHz, CDCl3): delta =15.25 (br s, 1H, -OH), 7.85 (d, 2H, J = 8.2 Hz, 2H,6H-Ph), 7.31 (d, 2H, J = 8.1 Hz, 3H,5H-Ph), 6.55 (s, 1H, -CH=), 2.45 (s, 3H, -CH3).?
95% With sodium; In methanol; at 20 - 80℃; for 10h; Sodium metal (5.76 g, 0.25 mol) was dissolved in methanol (80 ml), then trifluoroacetic acid (22 ml, 0.168 mol) was added at room temperature, followed by dropwise addition of methyl-acetophenone (21.04 g, 0.165 mol). The obtained mixture was stirred at 80 0C for 1O h, the reaction mixture was concentrated in vacuo and the residue was dissolved in water (50 ml). The solution was acidified by addition of IN hydrochloric acid (120 ml), extracted with ethyl acetate (2 x 80 ml), dried over MgSO4, filtered and concentrated in vacuo to yield 34.60 g (95 percent) of the title compound. The obtained crystalline product was used in the next step without further purification.
  • 7
  • [ 431-47-0 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In toluene; at 20 - 110℃; for 26h;Product distribution / selectivity; Sodium methoxide (25.6 g) and toluene (105 ml) were taken in a flask. A solution of 4-methylacetophenone (50 g) in toluene (52 ml) was added at 20-25° C. in 30 minutes. The resultant reaction mixture was stirred further at 20-25° C. for 30 minutes. A solution of methyltrifluoroacetate (56.8 g) in toluene (52 ml) was added slowly at 20-25° C. for about 1 hour and the reaction mixture was heated to about 110° C. for 24 hours. The reaction mixture was cooled to 30° C. and poured into a flask containing aqueous hydrochloric acid (210 ml, 3N). The layers were separated and the aqueous layer was extracted with toluene (2.x.50 ml). The organic layers were combined and washed with water (2.x.50 ml). The solvent was removed completely under vacuum to afford the title compound (Yield: 79 g).
With sodium methylate; In methanol; isopropyl alcohol; at 45℃; for 2h; In a 250 mL three-necked glass flask, p-methylacetophenone (10 g, 0.075 mol) and methyl trifluoroacetate (13.48,0.105111001), adding 2 (^ methanol sodium methanol solution (mass concentration of 28percent) and 401 ^ isopropanol, heated to 45 ° (after 2h holding, the temporary solution for the reaction a.
  • 8
  • [ 400-38-4 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In toluene; at 35 - 75℃; for 4h;Product distribution / selectivity; A mixture of 4-methylacetophenone (0.85 g), isopropyltrifluoroacetate (1.0 g) and toluene (2 ml) was added to a mixture of sodium methoxide (0.4 g) and toluene (2 ml) at 35-40° C. The reaction mixture was stirred at 75° C. for 4 hours. The reaction mixture was cooled to 25-30° C. Water (2 ml) and aqueous HCl (3 ml, 20percent) were added and the reaction mixture was stirred at 25-30° C. for 30 minutes. The layers were separated. Aqueous layer was extracted with toluene (2.x.2 ml). The organic layers were combined and the solvent was removed by distillation at 55° C. under vacuum to obtain the title compound (Yield: 1.0 g).
  • 9
  • [ 5417-17-4 ]
  • [ 122-00-9 ]
  • [ 399031-87-9 ]
  • 10
  • [ 122-00-9 ]
  • [ 1668-54-8 ]
  • [ 1465740-14-0 ]
  • 11
  • [ 92-55-7 ]
  • [ 122-00-9 ]
  • (3'R,4'R)-4'-(4-methylbenzoyl)-1'-methyl-3'-(5-nitro-2-furyl)spiro[indene-2,2'-pyrrolidine]-1,3-dione [ No CAS ]
  • 12
  • [ 383-62-0 ]
  • [ 17852-52-7 ]
  • [ 122-00-9 ]
  • 4-[5-(4-methylphenyl)-3-(chlorodifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Weigh 2.68g (20mmol) of 4-methyl acetophenone and 13.4ml methyl tert-butyl ether (MTBE), into the reaction flask and stir, 3.70g (23.3mmol) of <strong>[383-62-0]ethyl difluorochloroacetate</strong> was added,A 25% sodium methylate (24 mmol) solution in methanol was added dropwise at room temperature, and the mixture was heated to 45-55 C. during the dropwise addition and stirred for 24 hours.After the reaction was completed, the solvent was concentrated under reduced pressure to give a light yellow solid, which was stirred with 10% diluted hydrochloric acid (v / v) and extracted twice with ethyl acetate. The ethyl acetate layer solution into the reaction flask, add appropriate amount of ethyl acetate and water and stir, add 4.47g (20mmol) p-sulfonamidophenylhydrazine hydrochloride, warmed to 75-85 C, the reaction was stirred for 2 hours, the reaction Completed, room temperature cooling crystallization. Filtration, cake drying 60 C, 60% ethanol (m / m) that was recrystallized, HPLC purity of 99%.
  • 13
  • [ 354-31-4 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
91.2% In a 1000 mL three-necked flask,500 mL of ether was added and 68.0 g (1.0 mol) of sodium ethoxide and 134 g were added with stirring(1.0 mol) p-methylacetophenone, the reaction was heated to 40 ° C, the reaction 6 hours,The solvent was distilled off to give a yellow solid, which was partially dissolved by adding 300 ml of acetonitrile,To the reaction liquid, 230.1 g (1.3 mol)Trifluoroacetyl bromide, and reacted at 50 ° C for 3h. The filtrate was filtered off with suction, and part of the acetonitrile was distilled off to obtain 210g of white solid at -10 ° C, the content was 99.2percent and the yield was 91.2percent.
  • 14
  • [ 354-34-7 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
92.2% In a 1000 mL three-necked flask, 500 mL of isopropyl ether was added,Under stirring, 81 g (1.5 mol) of sodium methoxide and 134 g (1.0 mol) of p-methylacetophenone were added,The reaction was heated to 30 ° C, reacted for 6 hours, the solvent was distilled off,Add 250ml of m-dichlorobenzene partially dissolved, 127.6g (1.1mol) of trifluoroacetyl fluoride was passed into the reaction solution, and reacted at 40 ° C for 2h. The filtrate was suction filtered to remove some of the m-dichlorobenzene. At 10 ° C, a white solid was obtained 212g, content of 99.0percent, the yield was 92.2percent.
  • 15
  • [ 354-32-5 ]
  • [ 122-00-9 ]
  • [ 720-94-5 ]
YieldReaction ConditionsOperation in experiment
93% In a 1000 mL three-necked flask,500 mL of isopropyl ether was added and 81 g (1.5 mole) of sodium methoxide and 120.6 g (0.9 mole) of p-methylacetophenone were added with stirring. The reaction was heated to 50 ° C. After 6 hours of reaction, the solvent was distilled off and 250 ml of a toluene portion Dissolved, to the reaction solution was introduced 123g (1mol) trifluoroacetyl chloride, 40 reaction 2h, the filtrate was suction filtered, part of the toluene was distilled off,At -10 ° C, 172 g of a white solid was obtained in an amount of 99.0percent with a yield of 93.0percent.
  • 17
  • [ 5900-59-4 ]
  • [ 122-00-9 ]
  • 7-chloro-2-(4-methylbenzoyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With iodine; In dimethyl sulfoxide; at 110℃; for 12h; General procedure: DMSO (3 mL) was added to a mixture of acetophenone (1.0equiv.) and I2 (1.1 equiv.). The solutionwas stirred at 110 °C, then 2-aminobenzamide (1.0 equiv.) in 2mL DMSO was added dropwise tothe mixture during 1-2 h. After a complete disappearance of thestarting material, 50 mL water and 30 mL saturated brine wereadded to the mixture. The solution was extracted with CH2Cl2(50 mLx3). The organic layer was washed with 10percent Na2S2O3 solution, dried over anhydrous Na2SO4 and concentrated underreduced pressure. The residue was purified by silica gel chromatography(petroleum ether/EtOAc 5:1) to yield the desiredproducts 9a-9d.
  • 18
  • [ 186534-02-1 ]
  • [ 122-00-9 ]
  • C17H18N2O [ No CAS ]
  • 19
  • [ 16313-65-8 ]
  • [ 122-00-9 ]
  • 2-(4-methylbenzoyl)-6-nitro-4(3H)-quinazolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With iodine; In dimethyl sulfoxide; at 20 - 110℃; for 2h; 3 mL of p-methylacetophenone was dissolved in 10 mL of DMSO, and 2.8 g of iodine was slowly added.Add 3.6g at room temperature with stirring<strong>[16313-65-8]<strong>[16313-65-8]2-Amino-5-nitrobenzamid</strong>e</strong> dissolved in 20mLa solution of DMSO,The reaction was carried out at 110 C for 2 h.150 mL of water was added to the reaction system.Extracted with (3 × 60 mL) ethyl acetate.The iodine was removed by washing with (2×40 mL) saturated NaHSO3 solution.After washing with water, dry with anhydrous magnesium sulfate.Evaporate the solvent under reduced pressure.The residue was separated by chromatography (eluent: ethyl acetate: petroleum ether = 1:2).2-(4-methylbenzoyl)-6-nitro-4(3H)-quinazolinone 4.2 g,Yield 68%,Melting point 186-188 C.
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