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CAS No. : | 1122-54-9 | MDL No. : | MFCD00006433 |
Formula : | C7H7NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WMQUKDQWMMOHSA-UHFFFAOYSA-N |
M.W : | 121.14 | Pubchem ID : | 14282 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 34.43 |
TPSA : | 29.96 Ų |
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) : | -6.7 cm/s |
Log Po/w (iLOGP) : | 1.24 |
Log Po/w (XLOGP3) : | 0.48 |
Log Po/w (WLOGP) : | 1.28 |
Log Po/w (MLOGP) : | 0.13 |
Log Po/w (SILICOS-IT) : | 1.67 |
Consensus Log Po/w : | 0.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.32 |
Solubility : | 5.79 mg/ml ; 0.0478 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.68 |
Solubility : | 25.4 mg/ml ; 0.21 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.31 |
Solubility : | 0.589 mg/ml ; 0.00486 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
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: |
* 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 |
---|---|---|
>99% ee | With glucose; glucose dehydrogenase from Bacillus subtilis CGMCC 1.1398; medium-chain dehydrogenase from Kuraishia capsulate CBS1993; NAD In aq. phosphate buffer for 16 h; Enzymatic reaction | General procedure: Substrate scope and enantioselectivity determination The relative activities of 26 substrates were measured using thepreviously described assay protocol with adjusted ratio of enzymeand substrate concentration. The a-chloroacetophenone activitywas assumed 100percent.Enantioselectivity was determined by examining the reductionof aromatic ketones using an NADH-regeneration system consist-ing of the puried KcDH and glucose dehydrogenase (GDH) fromBacillus subtilis CGMCC 1.1398. The 1-mL reaction mixture con-tained 0.5 mM NAD+, 10 mM ketone, 1 U KcDH, 50 mg glucoseand 2 U GDH in 50 mM potassium phosphate buffer (pH 7.0). After16 h, the reaction sample was equally separated into two parts,with one terminated by adding an equal volume of methanol, fol-lowed by HPLC analysis to determine the conversion ratio, and theother extracted with ethyl acetate, followed by ee analysis. Meth-ods used for analysing chiral products using HPLC or GC aredescribed in Supplementary Table S1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78 % ee | With formic acid; triethylamine In tert-butyl methyl etherInert atmosphere | Triethylamine (315 mL, 2.26 mol) was added dropwise to formic acid (150 mL, 3.91 mol) with overhead stirring while maintaining the internal temperature below 60° C. with ice-bath cooling. Neat 4-acetylpyridine (100 mL, 0.904 mol) was then added rapidly while maintaining the temperature below 50° C. Following this addition, the reaction was allowed to cool to 28° C. and the chiral ruthenium catalyst [N-[(1R,2R)-2-(amino-N)-1,2-diphenylethyl]-2,4,6-trimethylbenzenesulfonamidato-N]chloro[(1,2,3,4,5,6-n)-1-methyl-4-(1-methylethyl)benzene]ruthenium (CAS No.177552-91-9; for catalyst preparation, see: Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R.; J. Am. Chem. Soc. 1996, 118, 4916-4917) (3 g, 4.46 mmol) was added. The mixture was stirred under house vacuum for 4 h and then overnight under an atmosphere of nitrogen. The reaction mixture was added dropwise to a stirred solution of 10percent Na2CO3 (4 L) and then extracted with EtOAc (3.x.1 L). The combined EtOAc layers were washed once with brine (1 L), treated with MgSO4 and Darco G-60 decolorizing charcoal and filtered through a 100 g plug of silica gel washing with 10percent MeOH/EtOAc (1 L). The filtrate was concentrated to provide a dark oil that crystallized upon standing. The solid was dissolved in warm t-butyl methyl ether (250 mL) and the warm solution was filtered to remove a small amount of insoluble material. The filtrate was allowed to stir with cooling to room temperature and then to -15° C. The solids were collected by filtration, washing with cold t-butyl methyl ether and heptane, and then dried under high vacuum to yield (1R)-1-(4-pyridinyl)ethanol as a dark beige solid (62 g, 52.9percent yield). This solid material was 96percent ee based on chiral HPLC (HPLC conditions: AS-H column, 5percent MeOH/CO2, 40° C., 140 bar, 2 mL/min). The filtrate was combined with the insoluble solid from the crystallization and concentrated in vacuo to yield additional (1R)-1-(4-pyridinyl)ethanol as a dark oil (37.5 g, 32percent yield). This oily material was 78percent ee based on chiral HPLC (see HPLC conditions above). 1H NMR (400 MHz, DMSO-d6): δ 8.47-8.43 (m, 2H), 7.32-7.28 (m, 2H), 5.37 (d, 1H, J=4.4 Hz), 4.72-4.64 (m, 1H), 1.44 (d, 3H, J=6.6 Hz). |
50 % ee | With hydrogen; lithium hydroxide; 9-amino-9-deoxyepicinchonine In methanol at 25℃; for 20 h; Autoclave | General procedure: Definite quantities of catalyst, chiral diamine, base, solvent, and heteroaromatic methyl ketones were placed into a 60mL stainless steel autoclave equipped with a magnetic stirrer bar. The autoclave was purged with hydrogen three times and the hydrogen pressure was increased to the desired level. The mixture was then stirred at room temperature for a suitable time. At the end of the reaction, the reactor was decompressed. Finally, the products were separated by centrifugation and analyzed by a GC instrument with an FID detector and β-DEX120 capillary column. The ee value was calculated from the equation: ee (percent)=100×(S−R)/(S+R). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogen bromide; bromine; acetic acid In water at 20℃; | EXAMPLE 14 Preparation of 2-bromo-1-pyridin-ylethanone hydrobromide To a stirred solution of 4-acetylpyridine (10 mL, 90 mmols) in glacial acetic acid (40 mL) and 48percent hydrobromic acid (15 mL), bromine (4.65 mL, 90 mmols) in glacial acetic acid (10 mL) was added dropwise. After addition, the solution was stirred at room temperature overnight. The white precipitate was filtered off and washed with absolute ethanol, thus obtaining the title compound (22.2 g Y=90percent) as a white solid containing traces of dibromoderivative, that was used as such in the next step. 1H NMR (DMSO-d6/400 MHz) δ ppm 5.05 (s, 2 H) 8.15 (d, 2 H) 9.0 (d, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 0 - 75℃; for 4 h; | 4-Bromoacetyl-pyridine, HBr salt; Dibromine (17.2g, 108 mmol) was added dropwise to a cold (0°C) solution of 4-acetyl- pyridine (12 g, 99 mmol) in acetic acid containing 33percent of HBr (165 mL) under vigourous stirring. The vigorously stirred mixture was warmed to 40°C for 2h and then to 75°C. After 2h at 75°C, the mixture was cooled and diluted with ether (400 mL) to precipitate the product. which was recovered by filtration and washed with ether and acetone to give white crystals (100percent). This material may be recrystallised from methanol and ether. |
98.1% | With N-Bromosuccinimide In ethyl acetate at 20 - 75℃; for 8 h; | The reaction bottle was added on the batch mother liquor 558g,Additional ethyl acetate 42g,121.1 g of 4-acetylpyridine was added with stirring,Stir well after 20 ~ 30 ° C batchwise add NBS186.9g;Add temperature slowly warmed to 65 ~ 75 ,TLC monitoring of raw materials reaction is completed, cooled to 0 ~ 10 full crystallization.Filtered, washed with 650g deionized water beating,Filtered again, dried to get white275.6 g of 4- (bromoacetyl) pyridine hydrobromide,The molar yield was 98.1percent, |
94% | With bromine In tetrachloromethane for 1 h; Reflux | To a stirred solution of l-(pyridin-4-yl)-ethanone (10 g, 0.08 mol) in CCl4 (150 mL) was added Br2 (3.99 mL, 0.02 mol) dropwise at 00C and the mixture was then refluxed for 1 h. The reaction mixture was filtered and dried in vacuo to afford 2-bromo-l -(pyridin-4- yl)-ethanone hydrobromide (22 g, 94percent) as a solid. |
90% | With hydrogen bromide; bromine; acetic acid In water at 20℃; | EXAMPLE 1 2-Bromo-1-pyridin-4-ylethanone hydrobromide To a stirred solution of 4-acetylpyridine (10 mL, 90 mmol) in glacial acetic acid (40 mL) and 48percent hydrobromic acid (15 mL), bromine (4.65 mL, 90 mmol) in glacial acetic acid (10 mL) was added dropwise. After addition, the solution was stirred at room temperature overnight. The white precipitate was filtered off and washed with absolute ethanol, thus obtaining the title compound (22.2 g, 90percent) as a white solid containing traces of dibromoderivative, that was used as such in the next step. 1H NMR (DMSO-d6/400 MHz) δ ppm 5.05 (s, 2 H) 8.15 (d, 2 H) 9.0 (d, 2 H). |
90% | With hydrogen bromide; bromine; acetic acid In water at 20℃; | Example 1; 2-Bromo-1 -pyridin-4-ylethanone hydrobromide; To a stirred solution of 4-acetylpyridine (10 mL, 90 mmo.) in glacial acetic acid (40 mL) and 48percent hydrobromic acid (15 mL), bromine (4.65 mL, 90 rnmoS) in giacial acetic acid (10 mL) was added dropwise. After addition, the solution was stirred at room temperature overnight. The white precipitate was filtered off and washed with absolute ethanol, thus obtaining the title compound (22.2 g, 90percent) as a white solid containing traces of dibromoderivative, that was used as such in the next step.1H NMR (DMSOd6 / 400 MHz) δ ppm 5.05 (s, 2 H) 8.15 (d, 2 H) 9.0 (d, 2 H). |
87% | at 20 - 70℃; for 1 h; | Step 1. 2-Bromo-1-lvridin-4-yl-ethanone. To a 0° C. solution of 4-acetylpyridine (4.90 g, 41.3 mmol) and 48percent HBr (7.0 mL) in acetic acid (46.0 mL) was added, dropwise over 15 min, a solution of Br2 (2.3 mL, 45 mmol) in acetic acid (8.0 mL). After the addition was complete, the mixture was allowed to warm to rt and then was heated at 70° C. for 1 h. The mixture was cooled to 0° C. and treated with diethyl ether. The resultant white solid was isolated by vacuum filtration to give 9.90 g (87percent) of the ketone as the HBr salt. MS: exact mass calcd for C7H6BrNO, 199.0; m/z found, 200.2 [M+H]+. |
85% | With hydrogen bromide; bromine; acetic acid In water at 70℃; for 3 h; | Preparation of 4-Bromoacetylpyridine, HBr saltHBrBromine (24 g, 150 mmol) in 4 mL of 45percent HBr was added drop wise under vigorous stirring to a solution at 70°C of 4-acetyl-pyridine (18 g, 148 mmol) in acetic acid containing 45percent of HBr (165 mL). The vigorously stirred mixture was kept at 700C for 3h. The mixture was cooled and the precipitate collected by filtration and washed with petroleum ether(40-65°C)/methanol (1/1, 100 mL) to give 35.8 g of a white crystals of (85percent). |
234.6 g | With bromine In tetrachloromethane for 1 h; Reflux | Bromine (131.92 g, 825.49 mmol) was added slowly at room temperature to a stirred solution of 3-1 (100 g, 825.491 mmol) in CC14 (2.5 L). The reaction mixture was then heated slowly to reflux for lh [reaction is exothermic and may be vigorous once it reaches 72 °C] . The product was precipitated out as light yellow solid. The reaction mixture was then cooled to room temperature and the product was collected by filtration, washed three times with diethyl ether (1.5 L in total) and dried to obtain compound 3-2 (234.6 g). |
0.72 g | With hydrogen bromide; bromine; acetic acid In water at 20℃; for 4 h; Cooling with ice | Intermediate C: Preparation of 2-bromo-l-(pyridin-4-yl)ethanone hydrobromide To a solution of l-(pyridin-4-yl)ethanone (1.0 g, 8.25 mmol) in HO Ac (60 mL) under ice bath was added aqueous HBr (1 mL, 48percent) and Br2 (1.45 g, 9.1 mmol) in HO Ac (20 mL). The mixture was stirred at rt for 4 h during which time a precipitate formed. Filtration of the solid provided 2-bromo-l-(pyridin-4-yl)ethanone hydrobromide (0.72 g, 3.6 mmol) as a yellow solid. LCMS [M+H]+ = 200.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dimethylsulfide borane complex; (2aS,4aR)-2,2-diphenylhexahydro-2H-1,7-dioxa-7b-aza-7a-boracyclopenta[cd]indene In toluene at 20℃; for 1.16667 h; Inert atmosphere | General procedure: BH3·SMe2 (2.0 M in toluene, 250 μL, 500 μmol) was added to a solution of the B-alkoxy oxazaborolidine 8 (7.43 mg, 25.0 μmol in toluene (1 mL), prepared prior to use according to procedure 1.2.6). After 15 min at 50 °C, the reaction mixture was adjusted to 20 °C and a solution of acetophenone (1a, 60.1 mg, 58.3 μL, 500 μmol) in toluene (1 mL) was continuously introduced over a period of 60 min via syringe pump. After addition, the reaction was stirred for additional 10 min and quenched with methanolic H2SO4 (1.1 M, 500 μL). The mixture was stirred for further 15 min and directly subjected to column chromatography (SiO2, pentane/Et2O 2:1) to give (R)-phenylethanol ((R)-2a, 58.3 mg, 477 μmol, 95percent, 97percent ee) as a colorless oil. |
88% | Stage #1: With borane*DMS In tetrahydrofuran at 20℃; for 7 h; Stage #2: With methanol In tetrahydrofuran at 0℃; for 12 h; Heating / reflux |
EXAMPLE 1bR-(+)-α-methyl-4-pyridinemethanolThe same reduction was performed using 1percent of catalyst 10 (1,3,2-dioxaborolan-2-yloxy)diphenylmethyl)pyrrolidine. Borane-DMS complex (10M, 1.6 mL, 16.00 mmol) was added to a solution of catalyst 10 (32 mg, 0.10 mmol) in dry THF (5 mL) at room temperature and the mixture was stirred for 1 hour. A solution of 4-acetylpyridine (1.21 g, 10.00 mmol) in THF (5 mL) was added for 5 h using an infusion pump. The reaction mixture was stirred at room temperature for over 1 hour, then cooled to 0° C. and quenched with methanol (10 mL). After refluxing for 12 h, the solvents were removed under vacuum, the residue was distilled (directly without chromatography purification) in a Kugelrohr apparatus under vacuum to give the final product as a white crystalline material (1.135 g, 92percent yield). Chiral GC of O-acetyl derivative indicated 98.8percent ee.; EXAMPLE 1cR-(+)-α-methyl-4-pyrydylmethanolThe same reaction was again performed using 10percent of catalyst 10 (1,3,2-dioxaborolan-2-yloxy)diphenylmethyl)pyrrolidine). Borane-DMS complex (10M, 1.7 mL, 17.00 mmol) was added to a solution of catalyst 10 (323 mg, 1.00 mmol) in dry THF (10 mL) at room temperature (during the addition hydrogen evolved) and mixture was stirred for 1 hour. A solution of 4-acetylpyridine (1.21 g, 10.00 mmol) in THF (5 mL) was added for 5 hours using an infusion pump. The reaction mixture was stirred at room temperature for over 1 hour, then cooled to 0° C. and quenched with methanol (10 mL). After refluxing for 12 hours, the solvents were removed under vacuum, the residue was distilled (directly without chromatography purification) in a Kugelrohr apparatus under vacuum to give the final product as white crystalline material (1.077 g, 88percent yield). Chiral GC of O-acetyl derivative indicated 99.0percent ee. |
85% | Stage #1: With borane*DMS In tetrahydrofuran Stage #2: With methanol In tetrahydrofuran at 0℃; for 4 h; Heating / reflux |
EXAMPLE 1aR-(+)-α-methyl-4-pyridylmethanolTo a 100 mL round flask equipped with a septa and nitrogen flow, 10percent of catalyst 6 (0.325 g, 1.0 mmol) was added. Then dry THF (30 mL) was added to make a solution. Borane complex with dimethyl sulfoxide 10.0 M (2.0 mL, 20.00 mmol) was added to the catalyst solution. The mixture was stirred for about 15 minutes. A solution of 4-acetylpyridine (1.211 g, 10.0 mmol) with dry THF (10 mL) was added to the reaction mixture during 1 hour. The reaction was allowed to react overnight. The reaction mixture was cooled to 0° C. MeOH (20 mL) was added and the mixture was heated to reflux for 4 hours. A sample of the mixture was analyzed by 11B-NMR and the N-BH3 complex signal was observed at -13.28 ppm. More MeOH (10 mL) was added and heated for 4 hours again. After decomposition of N-BH3 complex confirmed by 11B-NMR the mixture was concentrated to colorless oil. The residue was purified by column chromatography through Alumina (acid) (50 g) with an EtOAc/Hexane 1:1 mixture. The white crystalline α-methyl-4-pyridinemethanol was obtained in an 85percent yield (1.048 g.) (Mp°: 55°-58° C.) According with the G.C. analysis (Column: CP-Chirasil-Dex CB, Method: Iso135) the alcohol was observed at retention time 12.39 minutes and some aminoalcohol at retention time 11.64 minutes. The enantiomeric excess of 97.2percent ee was determined by 11P-NMR of the phosphorus derivative.An analysis of the product gave the following results:1H-NMR (400 MHz, CDCl3): δ1.39 (d, J=6.4 Hz, 3H); 4.80 (q, J=6.4 Hz, 1H); 5.096 (s, 1H); 7.22 (d, J=6.0 Hz, 2H); 8.309 (d, J=5.6 Hz, 2H) (98percent purity).13C-NMR (100 MHz, CDCl3): δ 24.99 (CH3); 68.21 (C-H(OH); 120.60 (CHAr); 148.97 (CHAr); 155.97.[α]23D=+49.0 (c=0.025, CHCl3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78 % ee | With formic acid; triethylamine In tert-butyl methyl etherInert atmosphere | Triethylamine (315 mL, 2.26 mol) was added dropwise to formic acid (150 mL, 3.91 mol) with overhead stirring while maintaining the internal temperature below 60° C. with ice-bath cooling. Neat 4-acetylpyridine (100 mL, 0.904 mol) was then added rapidly while maintaining the temperature below 50° C. Following this addition, the reaction was allowed to cool to 28° C. and the chiral ruthenium catalyst [N-[(1R,2R)-2-(amino-N)-1,2-diphenylethyl]-2,4,6-trimethylbenzenesulfonamidato-N]chloro[(1,2,3,4,5,6-n)-1-methyl-4-(1-methylethyl)benzene]ruthenium (CAS No.177552-91-9; for catalyst preparation, see: Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R.; J. Am. Chem. Soc. 1996, 118, 4916-4917) (3 g, 4.46 mmol) was added. The mixture was stirred under house vacuum for 4 h and then overnight under an atmosphere of nitrogen. The reaction mixture was added dropwise to a stirred solution of 10percent Na2CO3 (4 L) and then extracted with EtOAc (3.x.1 L). The combined EtOAc layers were washed once with brine (1 L), treated with MgSO4 and Darco G-60 decolorizing charcoal and filtered through a 100 g plug of silica gel washing with 10percent MeOH/EtOAc (1 L). The filtrate was concentrated to provide a dark oil that crystallized upon standing. The solid was dissolved in warm t-butyl methyl ether (250 mL) and the warm solution was filtered to remove a small amount of insoluble material. The filtrate was allowed to stir with cooling to room temperature and then to -15° C. The solids were collected by filtration, washing with cold t-butyl methyl ether and heptane, and then dried under high vacuum to yield (1R)-1-(4-pyridinyl)ethanol as a dark beige solid (62 g, 52.9percent yield). This solid material was 96percent ee based on chiral HPLC (HPLC conditions: AS-H column, 5percent MeOH/CO2, 40° C., 140 bar, 2 mL/min). The filtrate was combined with the insoluble solid from the crystallization and concentrated in vacuo to yield additional (1R)-1-(4-pyridinyl)ethanol as a dark oil (37.5 g, 32percent yield). This oily material was 78percent ee based on chiral HPLC (see HPLC conditions above). 1H NMR (400 MHz, DMSO-d6): δ 8.47-8.43 (m, 2H), 7.32-7.28 (m, 2H), 5.37 (d, 1H, J=4.4 Hz), 4.72-4.64 (m, 1H), 1.44 (d, 3H, J=6.6 Hz). |
50 % ee | With hydrogen; lithium hydroxide; 9-amino-9-deoxyepicinchonine In methanol at 25℃; for 20 h; Autoclave | General procedure: Definite quantities of catalyst, chiral diamine, base, solvent, and heteroaromatic methyl ketones were placed into a 60mL stainless steel autoclave equipped with a magnetic stirrer bar. The autoclave was purged with hydrogen three times and the hydrogen pressure was increased to the desired level. The mixture was then stirred at room temperature for a suitable time. At the end of the reaction, the reactor was decompressed. Finally, the products were separated by centrifugation and analyzed by a GC instrument with an FID detector and β-DEX120 capillary column. The ee value was calculated from the equation: ee (percent)=100×(S−R)/(S+R). |
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