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[ CAS No. 2815-95-4 ] {[proInfo.proName]}

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Chemical Structure| 2815-95-4
Chemical Structure| 2815-95-4
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Quality Control of [ 2815-95-4 ]

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Product Details of [ 2815-95-4 ]

CAS No. :2815-95-4 MDL No. :MFCD00016909
Formula : C10H10O4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :UIYJGLLTSVRSBM-UHFFFAOYSA-N
M.W : 194.18 Pubchem ID :64810
Synonyms :

Calculated chemistry of [ 2815-95-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.86
TPSA : 55.76 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.43
Log Po/w (MLOGP) : 1.1
Log Po/w (SILICOS-IT) : 1.91
Consensus Log Po/w : 1.58

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.2
Solubility : 1.22 mg/ml ; 0.00627 mol/l
Class : Soluble
Log S (Ali) : -2.43
Solubility : 0.714 mg/ml ; 0.00368 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.894 mg/ml ; 0.0046 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 2815-95-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2815-95-4 ]

* 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 [ 2815-95-4 ]

[ 2815-95-4 ] Synthesis Path-Downstream   1~17

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  • [ 7116-48-5 ]
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  • [ 6412-87-9 ]
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  • [ 2815-95-4 ]
  • [ 68996-81-6 ]
YieldReaction ConditionsOperation in experiment
100% With phosphorus pentachloride; In tetrahydrofuran; at 0℃; for 4h; 3.88 g of piperonyl propionic acid was placed in a 100 mL round bottom flask and then tetrahydrofuran was added in sequence.Phosphorus pentachloride, reacted at 0 C for 4 hours,The solvent was recovered under reduced pressure to obtain 4.24 g of a pale yellow liquid, piperonyl propionyl chloride, with a yield of 100%.Used without further purification for the next reaction.
With oxalyl dichloride; In DMF (N,N-dimethyl-formamide); dichloromethane; for 1h; To a solution of 3, 4-(methylenedioxy)dihydrocinnamic acid (0.4 [G)] in dry [CHUCK] (25 [ML)] under nitrogen, was added oxalyl chloride (0.5 ml) with three drops of dry DMF and the mixture stirred for 1 hour. Solvents were removed in vacuo giving the acid chloride as a yellow solid. To a solution of the acid chloride in dry [CHUCK] (50 [ML)] under nitrogen, cooled to [0C,] was added dropwise, a solution of 3, 4-(methylenedioxy) aniline (0.35 [G)] and pyridine (0.2 [ML)] in [CHZCLZ] (5 ml). The reaction mixture was stirred for 30 minutes at room temperature, diluted with CH2Cl2 (100 [ML),] washed with aqueous HCl (100 [ML,] [10%)] and sodium bicarbonate solution (100 [ML)] then dried and evaporated in vacuo to give DC-0057B as a dark brown powder (0.549g, [85%).] ['H-NMR] [(CDC13)] 7.15 [(1H,] d, [J] 2Hz), 6. 86 [(1H,] bs), 6.60-6. 75 [(5H,] m), 5.93 (2H, s), 5.92 (2H, s), 2.95 (2H, t, [J] 4Hz) and 2.57 (2H, t, [J 4HZ).]
With thionyl chloride; for 4h;Heating / reflux; In a 250 mL one-necked flask fitted with stirrer, the compound 72c (1.4 g) is dissolved into 20 ml SOCl2, and then heated at reflux for 4 h. When the mixture is cooled to room temperature, the solution is removed under vacuum, and the residue treated with 2.0 M NH3 in methanol (200 mL). The mixture was stirred for 30 min then concentrated under vacuum to afford 1.20 g of 72d as a white solid. The product was used directly in the subsequent step.
With thionyl chloride; at 79℃; for 4h; 3-Benzo[1,3]dioxol-5-yl-propionic acid (2.50 g, 12.9 mmol) and thionyl chloride (20 mL, 274 mmol) were heated to 79 C. for 4 h then concentrated to afford 3-(benzo[d][1,3]dioxol-5-yl)propanoyl chloride as a brown oil. 2-(2-Imidazol-1-yl-6-methyl-pyrimidin-4-yl)-2-methyl-propylamine (100 mg, 0.432 mmol) and methylene chloride (20 mL) were added and the reaction mixture stirred at rt for about 2 h. The reaction mixture was filtered, filtrate washed with K2CO3 (100 mL, sat. aq.), and the organic layer was dried over Na2SO4. Filtration, concentration and purification using column chromatography gave 40 mg of 3-benzo[1,3]dioxol-5-yl-N-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-2-methyl-propyl]-propionamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 7.92 (s, 1H), 7.05 (s, 1H), 6.90 (s, 1H), 6.70 (m, 3H), 5.90 (s, 2H), 3.59 (d, 2H), 2.94 (t, 2H), 2.57 (s, 3H), 2.40 (t, 2H), 1.28 (s, 6H).
With pyridine; thionyl chloride; In dichloromethane; at 0 - 20℃; for 1h; General procedure: A solution of 1 mmol of the corresponding propanoic acid mixed with one drop of pyridine in 10 mL of dichloromethane (DCM),cooled at 0C, was added dropwise to 1.2 mmol of thionyl chloride.After stirring for 1 h at rt, the crude was evaporated at reducedpressure. The crude was dissolved in DCM at 0 C and mixed with1.2 mmol of the corresponding amine reagent and with 0.8 mmol oftriethylamine. After stirring for 3 h, the crude was diluted with 40 mL of DCM and washed with water (3 100 mL). The organicphase was separated, dried with Na2SO4 and concentrated at reduced pressure. Purification was performed by silica gelchromatography.
With thionyl chloride; In toluene; for 4h;Reflux; General procedure: After dissolving the carboxylic acid in toluene (10 ml), SOCl2 (1 ml) was added and the reaction mixture was refluxed. The toluene was removed under vacuum and the crude mixture was dissolved in CH2Cl2 under N2 atmosphere. The alcohol and Et3N were added together to the solution and the reaction mixture was stirred at room temperature for some hours. Brine was added to the mixture and, then, it was extracted three times with CH2Cl2; the organic layers were collected, dried over Na2SO4 and the solvent was evaporated under reduced pressure.
With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 55℃; for 5h; General procedure: To a solution of carboxylic acid (1 equiv.) and SOCl2 (5 equiv) inCH2Cl2 (0.5 M) was added 3 drops of DMF. The reaction was refluxed at 55 C for 5 h. ThenCH2Cl2 and the excess SOCl2 (5 equiv) were removed by vacuum. The acyl chloride obtainedwas dissolved in CH2Cl2 (1 M) for the next step. After that, to a 0 C solution of8-Aminoquinoline (10.4 mmol, 1 equiv.) and NEt3 (1.05 equiv.) in CH2Cl2 (0.5 M) was added theacyl chloride (1.05 equiv.) solution dropwise over 10 min. The solution was allowed to warm toambient temperature and was stirred for 6 h. After that, the solution was washed with water (15mL), sat. NaHCO3 (15 mL) and brine (15 mL). The organic phase was dried over Na2SO4,concentrated and purified by flash chromatography to provide the desired product.
With oxalyl dichloride; In dichloromethane; for 4h;Inert atmosphere; To a stirred solution of carboxylic acid 30 (0.22 g,1.2 mmol) in CH2Cl2 (3 mL), under an atmosphere of nitrogen, was added oxalyl chloride (0.2 mL, 2.3mmol) dropwise and the mixture stirred for 4 h. The solvent was removed in vacuo to give the titlecompound 34b (0.24 g, quant.) as a green oil, which was placed under nitrogen and used withoutfurther purification.
With oxalyl dichloride; In dichloromethane; at 20℃; for 4h; 1,3-Benzodioxole -5-formaldehyde and malonic acid are used as starting materials, 1,3-benzodioxole -5-propionic acid is generated by simple redox reaction, corresponding amide is generated by nucleophilic substitution reaction with (S) 1,3 -benzyl -5 -2 -4-oxazolidinone under the action of n-butyl lithium, and at the same time, under the action of the ligand LiHMDS, it undergoes a nucleophilic substitution reaction with the bromopropyl group to produce the corresponding olefin, andis reduced, hydrolyzed, and oxidized under the catalysis of thecombined oxidant OsO4/NMO to produce the corresponding product, and then uses the strong reducing agent LiAlH4and the oxidizing agent NaIO4,the carbonyl compound is made into the corresponding hydroxyl compound by the two-step reaction of reduction and oxidation, and the Fetizon reagent is used to selectively oxidize it to the lactone, which is combined with 5-(bromomethyl)-1,3-benzodi The substitution reaction of catalyzer occurs under the action of LDA, and the final product is reduced with diisobutylaluminum hydride to obtain the product.

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 2984 - 2991
[2]Organic Letters,2017,vol. 19,p. 5368 - 5371
[3]Patent: CN104529994,2018,B .Location in patent: Paragraph 0037-0038; 0039-0040; 0041-0042
[4]Canadian Journal of Chemistry,1981,vol. 59,p. 3055 - 3060
[5]Chemische Berichte,1914,vol. 47,p. 1469
[6]Journal of the Chemical Society,1924,vol. 125,p. 1694
[7]Journal of Medicinal Chemistry,1990,vol. 33,p. 703 - 710
[8]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 1003 - 1005
[9]Tetrahedron Asymmetry,1994,vol. 5,p. 1219 - 1220
[10]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 1809 - 1820
[11]Bioscience, Biotechnology and Biochemistry,2003,vol. 67,p. 2183 - 2193
[12]Patent: WO2003/101927,2003,A1 .Location in patent: Page 42
[13]Patent: US2006/116515,2006,A1 .Location in patent: Page/Page column 58
[14]Patent: US2006/116515,2006,A1 .Location in patent: Page/Page column 87
[15]Synlett,2011,p. 425 - 429
[16]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2539 - 2542
[17]Journal of Organic Chemistry,2012,vol. 77,p. 4017 - 4028
[18]Journal of Organic Chemistry,2013,vol. 78,p. 6677 - 6687
[19]European Journal of Medicinal Chemistry,2013,vol. 69,p. 728 - 734
[20]Organic Letters,2011,vol. 13,p. 1944 - 1947
[21]European Journal of Medicinal Chemistry,2015,vol. 90,p. 351 - 359
[22]Synlett,2015,vol. 26,p. 2853 - 2857
[23]ChemMedChem,2017,vol. 12,p. 972 - 985
[24]Molecules,2018,vol. 23
[25]Patent: CN112979625,2021,A .Location in patent: Paragraph 0024; 0047-0048
  • 6
  • [ 2373-80-0 ]
  • [ 2815-95-4 ]
YieldReaction ConditionsOperation in experiment
99% With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 20℃; for 22h; To a solution of (3,4-methylenedioxy)-cinnamic acid (1 .5g, 7.8 mmol) in MeOH (200mL), acetic acid (10 mL) was added 10% Pd/C (500 mg) under N2 atmosphere. The mixture was stirred at room temperature for 22 hours under H2 atmosphere. Then the mixture was filtered through celite and washed with MeOH (200 mL). The filtrate was concentrated to give compound IntA-Q-12-1 as off-white crystalline solid (1.51 g, 99%).‘H NIVIR (400 MHz, CDC13) 5 6.74 - 6.64 (m, 3H), 5.92 (s, 2H), 2.87 (t, J= 7.8 Hz, 2H),2.63 (t, J 7.2 Hz, 2H).
80% Pd-C; In ethanol; 7.1 Synthesis of 3-benzo-1,3-dioxol-5-ylpropionic acid 3-benzo-1,3-dioxol-5-ylacrylic acid (2 g) was hydrogenated in ethanol (50 ml) over 5% Pd-C under a pressure of hydrogen at 10 psi for 40 mins to give 3-benzo-1,3-dioxol-5-ylpropionic acid (1.67 g, 80% yield) as a solid, m.p. 86.1-88.3 C. (Lit m.p. 87-88 C.)10
80% Pd-C; In ethanol; 7.1 Synthesis of 3-benzo-1,3-dioxol-5-ylpropionic Acid 3-benzo-1,3-dioxol-5-ylacrylic acid (2 g) was hydrogenated in ethanol (50 ml) over 5% Pd-C under a pressure of hydrogen at 10 psi for 40 mins to give 3-benzo-1,3-dioxol-5-ylpropionic acid (1.67 g, 80% yield) as a solid, m.p. 86.1-88.3 C. (Lit m.p. 87-88 C.)10.
80% Pd-C; In ethanol; 7.1 Synthesis of 3-benzo-1,3-dioxol-5-ylpropionic Acid 3-benzo-1,3-dioxol-5-ylacrylic acid (2 g) was hydrogenated in ethanol (50 ml) over 5% Pd-C under a pressure of hydrogen at 10 psi for 40 mins to give 3-benzo-1,3-dioxol-5-ylpropionic acid (1.67 g, 80% yield) as a solid, m.p. 86.1-88.3 C. (Lit m.p. 87-88 C.)10
palladium-carbon; In methanol; hydrogen; SYNTHESIS EXAMPLE 41 Synthesis of 3-(3,4-methylenedioxy-phenyl)-propionic acid In 5 ml of absolute methanol was dissolved 500 mg of 3,4-methylenedioxy-cinnamic acid, followed by adding thereto 50 mg of 10% palladium-carbon, and the reaction was carried out with stirring in a hydrogen stream at room temperature for 5 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was recrystallized from methanol to obtain 285 mg of the desired compound. NMR; (60 MHz, δ values in CDCl3), 2.71 (4H, --CH2 --CH2 --), 5.82 (2H, s, --O--CH2 --O--), 6.57 (3H, aromatic proton).

  • 9
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YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 16h; 10% Pd/C (1.2 g, 10 mol%) was placed in a 250 ml round-bottomed flask and the balloon replaced with hydrogen gas three times. After the hot ethanolDissolved compound 2b (12.0 g, 62.4 mmol) was added to the above reaction flask and stirred at room temperature for 16 hours. The reaction was monitored by TLC until the compound 2b reaction was complete. The reaction solution was filtered through celite, and the filtrate was evaporated to dryness under reduced pressure to remove the ethanol solvent to give an off-white solid 3b (m.p.=82-84C). The next reaction without further purification gave a crude yield of 74.3%.
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  • [ 174970-67-3 ]
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  • [ 2815-95-4 ]
  • [ 7031-03-0 ]
YieldReaction ConditionsOperation in experiment
96% 3-(Benzo[d][1,3]dioxol-5-yl)propanoic acid (3.61 g, 18.6 mmol) was dissolved in anhydrous THF (5 mL and added dropwise to a 0 C. solution of LiAlH4 (710 mg, 18.6 mmol) and anhydrous THF (100 mL). Upon completion of the addition, the reaction mixture was refluxed for 16 hours. The solution was then cooled to 0 C., water (10 mL) was added to the reaction and the solution was allowed to stir for 20 minutes. The solution was then extracted with ethyl acetate (3×20 mL). The organic layer was dried sodium sulfate and concentrated to afford 3.20 g (96%) of 78a.
With hydrogenchloride; In tetrahydrofuran; Step A 3-Benzo[1.3]dioxol-5-yl-propan-1-ol. Lithium aluminum hydride (1M in THF, 30 mL, 30 mmol) was added slowly to a solution of 3-benzo[1,3]dioxol-5-yl-propionic acid (5.83 g, 30 mmol) in THF (60 mL) at 0 C. The reaction was warmed to room temperature and was stirred for 2 h. The solution was added in portions to a mixture of ice (200 g) and concentrated HCl (2 mL). The product was extracted into EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 6:4) provided the title alcohol (4.51 g). 1H NMR (400 MHz, CDCl3) δ 6.73-6.62 (m, 3H), 5.91 (s, 2H), 3.66 (t, 2H), 2.63 (t, 2H), 1.84 (m, 2H).
With hydrogenchloride; In tetrahydrofuran; Step A 3-Benzo[1,3]dioxol-5-yl-propan-1-ol Lithium aluminum hydride (1M in THF, 30 mL, 30 mmol) was added slowly to a solution of 3-benzo[1,3]dioxol-5-yl-propionic acid (5.83 g, 30 mmol) in THF (60 mL) at 0 C. The reaction was warmed to room temperature and was stirred for 2 h. The solution was added in portions to a mixture of ice (200 g) and concentrated HCl (2 mL). The product was extracted into EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 6:4) provided the title alcohol (4.51 g). 1H NMR (400 MHz, CDCl3) δ6.73-6.62 (m, 3H), 5.91 (s, 2H), 3.66 (t, 2H), 2.63 (t, 2H), 1.84 (m, 2H).
With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 - 60℃; for 4h; The compound 3b (13.1 g, 67.6 mmol) was dissolved in 80 ml of tetrahydrofuran and pre-cooled in a 0C cold bath. Sodium borohydride (7.58 g, 202 mmol) was added portionwise to the above reaction solution, and then a solution of iodine (17.0 g, 67.6 mmol) in tetrahydrofuran (180 ml) was slowly added dropwise to the above reaction solution. After the iodine consumption was complete and no gas escaped, the reaction was transferred to a 60C oil bath and heated for 4 hours. The reaction was monitored by TLC until the reaction of compound 3b was complete. 26 ml of methanol was slowly added to the reaction solution at 0C to quench the reaction. The reaction mixture was poured into 200 ml of water and extracted three times with dichloromethane (80 ml). The organic phases were combined and the organic phase was backwashed with saturated saline. The organic phase was dried over anhydrous sodium sulfate and spin-dried to give a yellow color. The oil 4b was directly reacted without further purification.

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  • [ 2815-95-4 ]
  • [ 30830-55-8 ]
YieldReaction ConditionsOperation in experiment
78% General procedure: [0059] General procedure for the synthesis of compound (1v, 1y, 1ab) [0060] General procedure: To a dried 10 mL Schlenk tube was added acid (1 mmol, 1.0 equiv) and capped with rubber stopper. The tube is purged with N2 and protected by N2 in balloon.5 mL anhydrous DCM was added under N2. The solution was cooled to 0 C (ice bath) and 178 mg (1.1 mmol, 1.1 equiv) 1,1'-carbonyldiimidazole (CDI) were added. After stirring for 60 min, the colorless reaction solution was cooled to -78 C (dry ice/acetone bath) for 15 min. Subsequently, 1.75 mL (2.1 mmol, 2.1 equiv) of DIBAL-H solution (1.2 M in toluene) were added dropwise with a syringe throughout 10 min. The reaction mixture was stirred at -78 C for 1 h. The reaction mixture was quenched by the addition of 2 mL of EtOAc followed by 5 mL of tartaric acid solution (25 % in H2O) under vigorous stirring. The mixture was warmed up to RT and stirred vigorously for 15 min. The mixture was extracted with EtOAc (3 x 10 mL) and the combined organic extracts were washed with 1 M HCl (1 x 10 mL), saturated NaHCO3 (1 x 10 mL) and brine (1 x 10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product purified by flash chromatography on silica gel. [0061] 3-(benzo[d][1,3]dioxol-5-yl)propanal (1v) [0062] This substrate was synthesized following the general procedure. The crude product was purified by flash chromatography on silica gel (acetone/hexane = 1/9) to afford product (139 mg, 78% yield) as colorless oil.1H NMR (400 MHz, CDCl3) δ 9.79 (1H, t, J = 1.2 Hz), 6.72 (1H, d, J = 7.8 Hz), 6.67 (d, J = 1.5 Hz, 1H), 6.63 (dd, J = 7.9, 1.4 Hz, 1H), 5.91 (s, 2H), 2.87 (2H, t, J = 7.4 Hz), 2.72 (t, J = 7.3 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 201.32, 147.88, 146.04, 134.15, 121.15, 108.83, 108.36, 101.10, 45.55, 28.01.
  • 13
  • sodium-salt of/the/ 3<i>t</i>-benzo<1,3>dioxol-5-yl-acrylic acid [ No CAS ]
  • [ 2815-95-4 ]
  • 14
  • [ 67-56-1 ]
  • [ 2815-95-4 ]
  • [ 57906-98-6 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; at 20℃; for 0.5h;Inert atmosphere; General procedure: The corresponding carboxylic acid (1.0 mmol) andoxalyl chloride (10 mmol) were added to a 10 mL roundbottom flask equipped with a magnetic stirring bar. Arubber septum was used and the reaction was kept under a dry N2 atmosphere. The resulting solution was subjectedto stirring at room temperature for about 0.5 h and theevolution of the reaction was accompanied by TLC(indirectly by the reaction of an aliquot with methanolleading to the spontaneous formation of the correspondingmethyl ester). After the removal of oxalyl chlorideexcess the residue was dissolved in dry dichloromethane(3.0 mL). The resulting solution was added dropwiseto an ice-cooled mixture of hydrazine monohydrate(15 mmol) and dichloromethane (5 mL) placed in a 25 mLround bottom flask equipped with a stirring bar. A rubberseptum was used and the reaction was kept under a dryN2 atmosphere. After reaching room temperature (about30 min), the solvent was removed under reduced pressure.The product precipitated after the addition of ice waterto the previously obtained residue and was then filtered,leading to the formation of the desired hydrazides as asolid material (72-91% yield). All the hydrazides obtained,e.g., 11, 14, 16 and 19, were characterized by LRMS, 1Hand 13C NMR.
  • 15
  • [ 2815-95-4 ]
  • [ 16640-68-9 ]
  • 5-benzo[1,3]dioxol-5-yl-3-oxo-2-(triphenyl-λ5-phosphanylidene)-pentanenitrile [ No CAS ]
  • 16
  • [ 110-89-4 ]
  • [ 2815-95-4 ]
  • 1-[1-oxo-3-(3,4-methylenedioxyphenyl)propan]-piperidine [ No CAS ]
  • 17
  • [ 2815-95-4 ]
  • [ 74-89-5 ]
  • [ 33543-11-2 ]
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