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CAS No. : | 20637-08-5 | MDL No. : | MFCD09835999 |
Formula : | C12H16O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FEZIYDSIDIJXQH-UHFFFAOYSA-N |
M.W : | 208.25 | Pubchem ID : | 140725 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.42 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 58.41 |
TPSA : | 35.53 Ų |
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) : | -5.68 cm/s |
Log Po/w (iLOGP) : | 2.77 |
Log Po/w (XLOGP3) : | 2.66 |
Log Po/w (WLOGP) : | 2.19 |
Log Po/w (MLOGP) : | 2.25 |
Log Po/w (SILICOS-IT) : | 2.81 |
Consensus Log Po/w : | 2.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.71 |
Solubility : | 0.409 mg/ml ; 0.00196 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.06 |
Solubility : | 0.182 mg/ml ; 0.000876 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.82 |
Solubility : | 0.0314 mg/ml ; 0.000151 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.45 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | sulfuric acid; for 3h;Heating / reflux; | A mixture of 4- (4-methoxyphenyl) butyric acid (5.0 g, 25.8 mmol) and H2SO4 (concentrated, cat. amount) in MeOH (30 ml) was refluxed for 3 hr. The mixture was concentrated to remove excess MeOH. The residue was diluted with EtOAc (30 ml) and washed with H20 (20 ml), Sat. NaHCO3 (2 x 15 ml), Ha0 (20 ml), and brine (30 ml) respectively. The organic layer was then dried (MgS04), filtered. The filtrate was concentrated in vacuo to provide methyl 4- (4-methoxyphenyl) butyrate (5.3 g, 100%). 'H NMR (CDC13, 300 MHz) 6 1.89 (p, J = 6.6 Hz, 2H), 2. 30 (t, J = 7.2 Hz, 2H), 2.57 (t, J = 7.5 Hz, 2H), 3.64 (s, 3H), 3.76 (s, 3H), 6. 80 (d, J = 8.1 Hz, 2H), 7.07 (d, J = 8.1 Hz, 2H). |
97% | With sulfuric acid; at 20℃; for 16h; | To a solution of 4(4-Methoxyphenyl)-butyric acid (1) (10 g, 0.051 mol) in methanol (200 mL) was added concentrated sulfuric acid (1 mL) and the reaction mixture stirred at room temperature for 16 h. After concentration to remove methanol, the oil was dissolved in ethyl acetate (120 mL), washed with Na2CO3 (3*70 mL), water (100 mL), and brine (100 mL). The organic layer was dried (Na2SO4) and concentrated to give the methyl ester as an oil (10.34 g) in 97% yield. 1H NMR (CDCl3) delta 7.12 (d, 2H), 6.85 (d, 2H), 3.77 (s, 3H), 3.69 (s, 3H), 2.62 (t, 2H), 2.59 (t, 2H), 1.96 (t, 2H); 13C NMR (CDCl3) delta 173.9, 157.2, 133.3, 129.8, 128.7, 114.1, 113.1, 56.5, 53.6, 34.1, 33.2, 26.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With diisobutylaluminium hydride; In hexanes; dichloromethane; at -78℃; for 3h; | To a cooled solution of methyl 4- (4-methoxyphenyl) butyrate (3.6 g, 17.3 mmol) in CH2C12 (40 ml) at-78 C under N2 was added dropwise a solution of DIBAL in hexanes (1.0 M, 18.0 ml, 18 mmol). The resulting mixture was stirred at-78 C under N2 for 3 hrs, and then quenched by adding MeOH (-5 ml). The resulting mixture was warmed gradually to room temperature and filtered. The filtrate was concentrated in vacuo to give 4- (4-Methoxy-phenyl)-butyraldehyde as an oil (3.06 g, 100%). lH NMR (CDC13, 300 MHz) 8 1.91 (p, J = 7.5 Hz, 2H), 2.41 (t, J = 7.5 Hz, 2H), 2.58 (t, J = 7.5 Hz, 2H), 3.76 (s, 3H), 6.81 (d, J = 8.4 Hz, 2H), 8.07 (d, J = 8.4 Hz, 2H), 9.73 (s, 1H). The residue was used directly in the next step without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; | a) 5-(4-Methoxyphenyl)-1-(3-pyridinyl)-2-pentanone A solution of n-butyl lithium (28 ml of 1.6M in hexane, 0.124 mol) was added to a stirred solution of diisopropylamine (4.55 g, 0.045 mol) in dry tetrahydrofuran (50 ml) at 0C under a nitrogen atmosphere and the resulting yellow solution was stirred at 0C for 30 minutes. To the solution was added hexamethylphosphoramide (8.06g, 0.045 mol) and the resulting solution was stirred at 0C for 15 minutes. 3-Picoline (4.19g, 0.045 mol) was added to the reaction mixture and the resulting deep-red solution was stirred at 0C for 30 minutes. To the solution was added <strong>[20637-08-5]4-(4-methoxyphenyl)butyric acid methyl ester</strong> (9.36g, 0.045 mol) in dry tetrahydrofuran (20 ml). The resulting mixture was stirred at 0C for 15 minutes and then at room temperature for an additional 90 minutes. The pale-yellow solution was extracted with hydrochloric acid (300 ml of 1M). The acid solution was washed with ethyl acetate (2 * 250 ml), made basic using potassium hydroxide and extracted with ethyl acetate (4 * 200 ml). The combined extracts were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield a crude product. The crude product was purified by column chromatography (silica gel, chloroform) and recrystallized from ethyl acetate-hexane to yield 5-(4-methoxyphenyl)-1-(3-pyridinyl)-2-pentanone as a colorless crystalline solid, having a melting point of 35-37C and the following physical characteristics: Elemental analysis: C,75.31%, H,7.03%, N,5.11%; as against calculated values of C,75.31%; %,7.14%, N,5.17% for C17H19NO2·0.1H2O. 1H-NMR (delta-CDCl3): 1.82-1.98 (m,2H), 2.46-2.62 (m,2H), 2.53 (t,2H), 3.67 (s,2H), 3.79 (s,3H), 6.83 and 7.06 (ABq,4H), 7.23-7.31 (m,1H), 7.29-7.37 (m,1H), 8.39-8.46 (m,1H) and 8.50-8.56 (m,1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sulfuric acid; In methanol; | Step A: Preparation of Methyl 4-(4-methoxyphenyl)-butyrate To a solution of 4-(4-methoxyphenyl)-butyric acid (25.1 g, 0.129 mol) in methanol (130 mL), was added sulfuric acid (concentrated, 1.0 mL) dropwise and it was stirred at room temperature overnight under nitrogen. The reaction mixture was concentrated on a rota-vapor, the residue was then partitioned between ethyl acetate (200 mL) and saturated sodium bicarbonate aqueous solution (200 mL). The organic phase was separated, washed with brine (3*200 mL), then dried over Na2SO4 and filtered. Evaporation of solvent gave the titled compound as an oil (26.8 g, 99%). Mass (MH+)=209. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium(III) triflate; palladium diacetate; triphenylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene; at 95℃; under 26252.6 Torr; for 4h;Catalytic behavior; | General procedure: Al(OTf)3 (10 mol%), Ph3P (20 mol%), xylene (0.5 g), and the appropriate alkene (4 mmol) were added together in the Parr reactor and dissolved in MeOH (6 mL). The reactor was degassed and allowed to heat up to 95 C. Pd(OAc)2 (5 mol%) dissolved in MeOH (2 mL) was injected, whereafter the pressure was set to 35 bar of CO. Conversions, yields, and product ratios were determined utilizing a Shimadzu 2010 GC instrument with xylene as the internal standard (Tables 2-4). Where applicable, the products were directly purified by flash column chromatography [100 g Merck Kieselgel 60 (230-400 mesh) per gram of crude mixture] with the eluent as indicated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium(III) triflate; palladium diacetate; triphenylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene; at 95℃; under 26252.6 Torr; for 4h;Catalytic behavior; | General procedure: Al(OTf)3 (10 mol%), Ph3P (20 mol%), xylene (0.5 g), and the appropriate alkene (4 mmol) were added together in the Parr reactor and dissolved in MeOH (6 mL). The reactor was degassed and allowed to heat up to 95 C. Pd(OAc)2 (5 mol%) dissolved in MeOH (2 mL) was injected, whereafter the pressure was set to 35 bar of CO. Conversions, yields, and product ratios were determined utilizing a Shimadzu 2010 GC instrument with xylene as the internal standard (Tables 2-4). Where applicable, the products were directly purified by flash column chromatography [100 g Merck Kieselgel 60 (230-400 mesh) per gram of crude mixture] with the eluent as indicated. |
Tags: 20637-08-5 synthesis path| 20637-08-5 SDS| 20637-08-5 COA| 20637-08-5 purity| 20637-08-5 application| 20637-08-5 NMR| 20637-08-5 COA| 20637-08-5 structure
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