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[ CAS No. 33689-29-1 ] {[proInfo.proName]}

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Chemical Structure| 33689-29-1
Chemical Structure| 33689-29-1
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Quality Control of [ 33689-29-1 ]

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Product Details of [ 33689-29-1 ]

CAS No. :33689-29-1 MDL No. :MFCD02093884
Formula : C5H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :KPJWVJURYXOHOO-UHFFFAOYSA-N
M.W : 116.12 Pubchem ID :2733178
Synonyms :

Calculated chemistry of [ 33689-29-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 26.52
TPSA : 46.53 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : -0.19
Log Po/w (WLOGP) : -0.38
Log Po/w (MLOGP) : -0.38
Log Po/w (SILICOS-IT) : 0.43
Consensus Log Po/w : 0.18

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.31
Solubility : 57.1 mg/ml ; 0.492 mol/l
Class : Very soluble
Log S (Ali) : -0.33
Solubility : 54.2 mg/ml ; 0.466 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.15
Solubility : 83.0 mg/ml ; 0.714 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 33689-29-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 33689-29-1 ]

* 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 [ 33689-29-1 ]

[ 33689-29-1 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 110-87-2 ]
  • [ 33689-29-1 ]
  • [ 87326-00-9 ]
YieldReaction ConditionsOperation in experiment
86% pyridinium p-toluenesulfonate; In dichloromethane; at 25℃; for 3h; Hydroxy-cyclopropanecarboxylic acid methyl ester (5.07 g, 43.71 mmol) was dissolved in methylene chloride (75 mL) and 3,4-dihydro-2H-pyran (3.86 g, 45.90 mmol) was added followed by pyridinium-p-toluene-sulfonic acid (1.10 g, 4.37 mmol). The reaction stirred at 25 C. for 3 h. The reaction was concentrated in vacuo to give a clear oil. The oil was dissolved in diethyl ether (75 mL), washed with saturated aqueous brine solution (25 mL), dried over sodium sulfate and concentrated in vacuo to an oil. The oil was passed through a plug of silica gel (Merck silica gel 60, 40-63 mum; 100% ethyl acetate) to afford 1-(tetrahydro-pyran-2-yloxy)-cyclopropanecarboxylic acid methyl ester (7.49 g, 86%) as a clear oil: H1-NMR (400 MHz, CDCl3) delta 1.14-1.42 (4H, m), 1.88-3.46 (6H, m), 3.46-3.54 (1H, m), 3.70-3.72 (3H, m), 3.82-3.90 (1H, m), 4.81-4.96 (1H, m).
60% With pyridinium p-toluenesulfonate; In dichloromethane; at 23℃; for 16h;Sealed tube; Methyl 1-hydroxycyclopropanecarboxylate (1.12 g, 9.65 mmol) was dissolved in DCM (15 mL) and3,4-dihydro-2H-pyran (0.9 mL, 10.13 mmol) was added, followed by pyridmnium p-toluenesulfonate (0.242 g, 0.965 mmol). The colorless solution was stirred at RT in a sealed vessel for 16 h. The reaction mixture was concentrated in vacuo. The white suspension was partitioned between brine (20 mL) and Et20 (20 mL) and the layers were separated. The organic layer was washed with brine (2x 5mL) and dried on Na2504 before concentration in vacuo. The product was purified using CC (silica, gradient heptane/EtOAc, 1:0-. 8:2)to give the desired product (1.16 g, 60%) as a colorless oil.
  • 2
  • [ 67-56-1 ]
  • [ 17994-25-1 ]
  • [ 33689-29-1 ]
  • 3
  • [ 33689-28-0 ]
  • [ 124-41-4 ]
  • [ 33689-29-1 ]
  • 4
  • [ 66324-10-5 ]
  • [ 33689-29-1 ]
  • methyl 2,6-dioxo-6-phenylhexanoate [ No CAS ]
  • 5
  • [ 33689-29-1 ]
  • [ 87326-01-0 ]
  • 6
  • [ 33689-29-1 ]
  • [ 814-49-3 ]
  • 1-(Diethoxy-phosphoryloxy)-cyclopropanecarboxylic acid methyl ester [ No CAS ]
  • 7
  • [ 33689-29-1 ]
  • [ 18162-48-6 ]
  • [ 90660-08-5 ]
YieldReaction ConditionsOperation in experiment
86% With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 60h; A solution of methyl 1-hydroxy-1-cyclopropane carboxylate (2.03 g, 17.5 mmol)DMF (35 mL) was treated sequentially with imidazole (1.19 g, 17.5 mmol) and tertbutyldimethylsilyl chloride (2.77 g, 18.4 mmol). The resulting mixture was stirred for 60 h at ambient temperature. The reaction mixture was diluted with water, and extracted with Et20 (2x). The organic extracts were washed with water (3x) and brine (lx), then dried over anhydrous Na2SO4(), filtered and concentrated in vacuo to afford the title compound (3.45 g, 86% yield). ?H NMR (400 IVIHz, CDC13) 3.71 (s, 3H), 1.33-1.30 (m, 2H), 1.08-1.05 (m, 2H), 0.87 (s, 9H), 0.14 (s, 6H).
With 1H-imidazole; In dichloromethane; for 12h;Inert atmosphere; Step 1 Methyl 1-(tert-butyldimethylsilyloxy)cyclopropanecarboxylate Methyl 1-hydroxycyclopropanecarboxylate 5a (350 mg, 3.02 mmol) was dissolved in 30 mL of dichloromethane, followed by addition of tert-butyldimethylsilyl chloride (495 mg, 3.30 mmol) and imidazole (306 mg, 4.49 mmol). After reacting for 12 hours, the reaction mixture was mixed with 20 mL of dichloromethane, and extracted with saturated sodium chloride solution (20 mL*3), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title product methyl 1-(tert-butyldimethylsilyloxy)cyclopropanecarboxylate 5b (600 mg, colourless oil), which was used directly in the next step without further purification.
With 1H-imidazole; In dichloromethane; at 20 - 30℃; for 12h; Methyl 1-hydroxycyclopropanecarboxylate 5a (350 mg, 3.02 mmol) was dissolved in 30 mL of dichloromethane, followed by addition of tert-butyldimethylsilyl chloride (495 mg, 3.30 mmol) and imidazole (306 mg, 4.49 mmol). After reacting for 12 hours, the reaction mixture was mixed with 20 mL of dichloromethane, and extracted with saturated sodium chloride solution (20 mL*3), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title product methyl 1-(tert-butyldimethylsilyloxy)cyclopropanecarboxylate 5b (600 mg, colourless oil), which was used directly in the next step without further purification.
  • 8
  • [ 33689-29-1 ]
  • [ 107-30-2 ]
  • [ 910310-53-1 ]
  • 9
  • [ 33689-29-1 ]
  • 1-Trimethylsilanyloxy-cyclopropanecarboxylic acid methyl ester [ No CAS ]
  • 10
  • [ 33689-29-1 ]
  • [ 74-88-4 ]
  • [ 2790-74-1 ]
YieldReaction ConditionsOperation in experiment
98% Example B6 A 0 C. solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropane-1-carboxylate</strong> (1 g, 8.61 mmol) in DMF (10 mL) was treated with NaH (60% in mineral oil, 0.689 g, 17.22 mmol), stirred at 0 C. for 0.5 h, treated with iodomethane (0.646 mL, 10.33 mmol), allowed to slowly warm to RT and stirred for 2 h. The mixture was quenched with satd. NH4Cl, diluted with water and extracted with Et2O (3*). The combined organics were washed with water, then brine, dried and concentrated to afford methyl 1-methoxycyclopropane-1-carboxylate (1.10 g, 98%). 1H NMR (400 MHz, DMSO-d6): delta 3.62 (s, 3H), 3.27 (s, 3H), 1.12-1.11 (m, 4H).
98% Example B18 A 0 C. solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropane-1-carboxylate</strong> (1 g, 8.61 mmol) in DMF (10 mL) was treated with NaH (60% in mineral oil, 0.689 g, 17.22 mmol), stirred at 0 C. for 0.5 h, treated with iodomethane (0.646 mL, 10.33 mmol), allowed to slowly warm to RT and stirred for 2 h. The mixture was quenched with satd. NH4Cl, diluted with water and extracted with Et2O (3×). The combined organics were washed with water, then brine, dried and concentrated to afford methyl 1-methoxycyclopropane-1-carboxylate (1.10 g, 98%). 1H NMR (400 MHz, DMSO-d6): delta 3.62 (s, 3H), 3.27 (s, 3H), 1.12-1.11 (m, 4H).
With sodium hydride; In tetrahydrofuran; at 0℃; for 18h; Step A: 1-METHOXV-CVCLOPROPANECARBOXYLIC acid methyl ester 1-Hydroxy-cyclopropanecarboxylic acid methyl ester (1.16 gm, 10 MMOL) was dissolved in 10 ml of tetrahydrofuran and cooled under a nitrogen atmosphere to 0 C. Sodium hydride (0.52 gm, 60 % oil dispersion) was added portionwise followed by lodomethane (1 ml) and stirred for 18 hrs. The reaction mixture was quenched with ammonium chloride and extracted with ETHYLACETATE to obtain 2 gm of title product. (MH+= 130)
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 18h; According to WO 2005/014577 methyl l-hydroxycyclopropanecarboxylate (1.01 g, 8.70 mmol) was dissolved under argon in THF (10 ml) and cooled using an ice-bath. Sodium hydride (60%, 0.52 g, 13.00 mmol) was added portionwise followed by iodomethane (1 ml, 16.06 mmol) and the mixture was stirred for 18 hours at room temperature. The mixture was quenched with saturated solution OfNH4Cl (20ml) and extracted with EtOAc. The organic extracts were combined, dried, filtered and evaporated in vacuo to give 620 mg of the crude product which was used as such.1H NMR (400 MHz, CDCl3) delta 3.76 (s, 3H), 3.43 (s, 3H), 1.25-1.17 (b, 4H),
4.0 g To a solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropanecarboxylate</strong> (3.2 g) in tetrahydrofuran (40 ml), sodium hydride (55% oil, 1.3 g) was added under ice cooling, and the mixture was stirred at the same temperature as above for 15 minutes. Methyl iodide (2.3 ml) was added to the reaction solution, and the mixture was stirred overnight at room temperature. 1 N hydrochloric acid was added to the reaction solution, followed by extraction with a n-hexane-ethyl acetate mixed solution. The extract was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (4.0 g). 1H-NMR (CDCl3) delta: 1.13-1.32 (4H, m), 3, 42 (3H, s), 3.75 (3H, s).
00512] Step A: NaH (738 mg, 18.44 mmol; 60% dispersion in oil) was added to a solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropanecarboxylate</strong> (1.83 g, 14.18 mmol) in anhydrous THF (15 mL) cooled on an ice bath. The mixture was stirred for 15 minutes then iodomethane (3.22 g, 1.42 mL, 22.69 mmol) was added slowly, and the resulting mixture stirred at ambient temperature for 18 hours. The reaction mixture was quenched with ammonium chloride and extracted with EtOAc (3 X 20 mL). The combined organic extracts were washed with water, <n="167"/>dried over MgSO4, and filtered. The filtrate was evaporated under reduced pressure to give methyl 1-methoxycyclopropanecarboxylate.

  • 11
  • [ 17994-25-1 ]
  • [ 33689-29-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; triethylamine; In methanol; Preparation of Methyl 1-hydroxy-1-cyclopropanecarboxylate 1-Hydroxy-1-cyclopropanecarboxylic acid (587 mg, 5.75 mmol) was dissolved in methanol (20 mL) under nitrogen. Thionyl chloride (4 drops) were added and the reaction was stirred overnight at room temperature. Triethylamine was then added until the reaction was alkaline as judged by moistened pH paper. The solvent was then removed on the rotary evaporator.
  • 12
  • [ 6299-25-8 ]
  • [ 33689-29-1 ]
  • [ 1190735-24-0 ]
YieldReaction ConditionsOperation in experiment
98% To a solution of Compound 1 ( 5.00 g, 25.6 mmol ) and methyl 1-hydroxy-l- cyclopropane carboxylate ( 3.97 g, 30.8 mmol ) in THF ( 100 mL ) was added sodium hydride ( 60 %, 1.23 g, 30.8 mol ) at -78 C and the mixture was stirred at room temperature for 3hours. The reaction mixture was quenched with 1 M aqueous citric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography ( hexane : ethyl acetate = 15 : 1 ) to give Compound 2 ( 6.91 g, 98 % ) as a solid. MS: 275/277 [M+H]+, APCI
  • 13
  • [ 33689-29-1 ]
  • [ 329-59-9 ]
  • [ 959937-72-5 ]
YieldReaction ConditionsOperation in experiment
e) 4-(1 -Methoxycarbonylcvclopropoxy)-3-nitrobenzoic acid methyl ester; To a suspension of 20.81 mmol of sodium hydride in 10 ml of dry N,N-dimethyl- formamide at 00C is added a solution of 17.34 mmol of methyl 1 -hydroxy-1 - cyclopropane carboxylate in 10 ml of dry N,N-dimethylformamide. The reaction mixture is stirred at 00C for 1 hour, before the addition of 27.74 mmol of methyl 4-fluoro-3-nitrobenzoate. The reaction mixture is stirred at 00C for 1 hour, then at room temperature for 3 hours, poured onto saturated aqueous ammonium chloride, <n="57"/>extracted with tert-butyl methyl ether (3X), dried over sodium sulphate and concentrated. Purification by flash chromatography (SiO2 60F) affords the title compound as a thick yellow oil. Rf = 0.48 (EtOAc-heptane 1 :1 ); Rt = 4.18 (gradient I).
  • 14
  • [ 33689-29-1 ]
  • [ 100-39-0 ]
  • [ 865798-43-2 ]
YieldReaction ConditionsOperation in experiment
Step 1. Methyl 1-(benzyloxy)cyclopropanecarboxylate At 0 C., methyl 1-hydoxycycloprppanecarboxylate was added to a suspension of NaH and DMF. After stirring for 10 min., benzylbromide was added and the reaction mixture was allowed to gradually warm to rt while stirring overnight. The reaction mixture was poured into ice water and extracted with ether (3*100 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in-vacuo. The crude product was purified by flash chromatography, eluding with hexane/ether (3:1, 2:1, 1:1, 1:2) to give 600 mg of yellow oil. 1H NMR confirmed the structure of the isolated product.
  • 16
  • [ 1202376-60-0 ]
  • [ 33689-29-1 ]
  • [ 1202376-48-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; In dichloromethane; at 20℃; for 14h;Inert atmosphere; To a stirred solution of 2-(4-(quinolin-2-ylmethoxy) phenyl) acetyl chloride (2.0 g, 6.557 mmol) in DCM (50 mL), DMAP (1.4 g, 13.114 mmol) was added followed by methyl 1- hydroxycyclopropanecarboxylate (1.1 g, 9.836 mmol) under a nitrogen atmosphere at RT and the mixture was stirred for 14 h. After complete consumption of the starting material (by TLC), the reaction mixture was quenched with water (10 mL) and the aqueous layer was extracted with DCM (2 x 50 mL). The combined organic layers were washed with a saturated NaHCO3 solution (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford crude methyl l-(2-(4-(quinolin-2-ylmethoxy) phenyl) acetoxy) cyclopropanecarboxylate (2.0 g,) as a solid.
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; ;