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CAS No. : | 4640-67-9 | MDL No. : | MFCD00662062 |
Formula : | C9H6FNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LOJBBLDAJBJVBZ-UHFFFAOYSA-N |
M.W : | 163.15 | Pubchem ID : | 2783172 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.15 |
TPSA : | 40.86 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) : | -6.54 cm/s |
Log Po/w (iLOGP) : | 1.24 |
Log Po/w (XLOGP3) : | 1.07 |
Log Po/w (WLOGP) : | 2.34 |
Log Po/w (MLOGP) : | 1.51 |
Log Po/w (SILICOS-IT) : | 2.43 |
Consensus Log Po/w : | 1.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.76 |
Solubility : | 2.81 mg/ml ; 0.0172 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.52 |
Solubility : | 4.93 mg/ml ; 0.0302 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.11 |
Solubility : | 0.128 mg/ml ; 0.000783 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
47% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: at -78 - -60℃; for 3 h; |
At -780C to n-BuLi (2.5 M in Hexane, 27 mL, 67.8 mmol, 1.0 equiv.) in THF (200 mL) was added CH3CN (3.9 mL, 3.06 g, 74.6 mmol, 1.1 Equiv.) slowly, after stirring for 1 hr., 4-F-benzoate ethyl ester (V9, 11.4 g, 67.8 mmol) in THF (10 mL) was added, and the reaction mixture was stirred at this temperature for another hr. The reaction was warmed to -6O0C, stirred for 2 hrs, and diluted with EtOAc, washed with brine, dried over MgSO4, filtered, and evaporated. The crude reaction mixture was recrystalized from EtOAc to afford compound 10 (5.20 g, 31.9 mmol, yield 47percent). 1H NMR (CDCI3) δ: 8.00-7.92 (m, 2H), 7.23-7.18 (m, 2H), 4.06 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: With [2,2]bipyridinyl; n-butyllithium; magnesium sulfate In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere Stage #2: at -78 - 20℃; Inert atmosphere Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; hexane; water |
General procedure: Cyanoacetic acid (1.7 g, 20 mmol, 2 equiv), 0.2 mg MgSO4, and ~1 mg 2,2'-bipyridyl was dissolved in tetrahydrofuran (100 mL) and placed in a 500 mL three-neck flask fitted with two dropping funnels and a mechanical stirrer. The system was flushed with nitrogen and cooled to -78 C with a dry ice/ acetone bath. An n-butyl lithium solution (25 mL, 1.6 M in hexanes; 40 mmol, 4 equiv) was added via a dropping funnel with stirring. Once the solution turned slightly purple it was stirred (30 min) after which the acid chloride (10 mmol, 1 equiv) in 5 mL of methanol was added drop-wise with stirring. During this process, the cloudy solution took on a yellow color. The solution was stirred at -78 C for one hour, then the bath was removed and the reaction was allowed to return to room temperature for one hour. An HCl solution (50 mL, 1M) was added drop-wise. At this point, the reaction became clear, while remaining yellow. Water (25 mL) and CH3Cl (50 mL) were added. The aqueous layer was extracted three times with the same volume of CH3Cl. The combined organic layers were washed with two portions (50 mL) of saturated sodium bicarbonate solution and dried over magnesium sulfate, filtered, and reduced on a rotoevaporator. Samples were purified by flash chromatography 6 Hex : 1 EtOAc resulting in percent yields from 50-80percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.14% | Stage #1: With sodium hydride In toluene at 90℃; for 2 h; Stage #2: for 6.5 h; |
To a 2 L three-necked round-bottomed flask were added toluene (1050 mL), 60percent NaH (78.20 g, 1.95 mol) and acetonitrile (79.85 g, 1.95 mol), and a solution of methyl fluorobenzoate (150.15 g, 0.96 mol) After heating to 90 ° C, acetonitrile (79.85 g, 1.95 mol) was added after 2 h. After 6.5 h the heating was stopped. After cooling, the filtrate was filtered and the cake was added to water (1650 mL) / L hydrochloric acid adjusted to pH 6 and extracted with dichloromethane (750 mL * 4). The combined methylene chloride layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to dryness to give yellow solid 3 (141.08 g, 93.14percent ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hexamethyldisilazane In tetrahydrofuran; toluene at -5 - 0℃; Large scale | Methyl 4-fluorobenzoate (29.44 kg), toluene (177 L) and acetonitrile (59 L; 5.9 mol equivalents versus methyl 4-fluorobenzoate) were charged to the reactor. The mixture was cooled to a temperature of -5 / 0 ° C. A solution of sodium bis (trimethylsilyl) amide (NaHMDS 40percent in THF) (192 L; 2 mol / mol vs. methyl 4-fluorobenzoate) was added while maintaining the temperature between -5 / + 5 ° C. The addition line was washed off with toluene (9 L). The reaction mixture was quenched by adding dilute hydrochloric acid while maintaining the temperature of -5 / + 25 ° C. The addition of acid was continued until pH <5. The layers separated and the lower aqueous layer was removed. The solvent was removed by vacuum distillation to a small amount. Toluene (59 L) was added and the mixture was heated to 85/90 ° C. to give a solution. The mixture was cooled to T = 50/55 ° C. and n-heptane (29 L) was added to obtain a precipitate. The mixture was further cooled to T = 20/25 ° C. and the solid product was isolated by filtration and washed with n-heptane (59 L). The product in the moist state was dried under vacuum at T = 40/45 ° C. to give 4-fluorobenzoylacetonitrile (26 kg, yield 83percent) of purity 98.7percent Apercent GC. The amount of 4-methoxybenzoylacetonitrile as an impurity was 0.03percent (Apercent GC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sodium hydride In tert-butyl methyl ether; water at 90℃; | Methyl 4-fluorobenzoate (50 g)Was added to a suspension of sodium hydride in methyl-tert-butyl ether (MTBE)(2 eq.) At 90 ° C.4-fluorobenzoylacetonitrile was obtained in about 64percent yield.4-fluorobenzoic acid with a purity of 81percent, 17.5percent4-methoxybenzoylacetonitrile was about 3percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | Stage #1: at 20℃; for 2 h; Stage #2: With hydrogenchloride In ethanol; water |
To a stirred suspension of 2.5 g (11.5 mmol) 2-bromo-l-(4-fiuoro-phenyl) -ethanone in 40 ml ethanol was added a solution of 0.90 g (23 mmol) potassium cyanide in 9 ml water. The mixture was then stirred at RT for 2 h, then acidified to ph=5-6 with aqueous HCl IM and then extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane / ethyl acetate 6:1) afforded 0.11 g (6 percent) 3-(4-fluoro-phenyl)-3-oxo-propionitrile as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.9 g | With hydrogenchloride In water at 20℃; for 3 h; | To three-necked flask was added potassium tert-butoxide and isopropyl ether,A mixed solution of 68 g of acetonitrile / 8 g of t-butanol / 400 mL of isopropyl ether / 100 g of p-fluorobenzonitrile was added dropwise with stirring, and the temperature of the dropwise addition was controlled within the range of 10 ° C to 25 ° C.After the addition was completed, the temperature of the reaction system was maintained at 27 ° C to 30 ° C for 22 hours.After the reaction of TLC detection raw material was completed, 400 mL of water was added to quench the reaction, and the quenching temperature was controlled below 30 ° C.Then, the isopropyl ether was distilled off under reduced pressure at room temperature, extracted with 600 mL of dichloromethane and separated. The aqueous layer was further extracted with dichloromethane (300 mL × 2). The combined organic phase was ready for further reaction.To the organic phase was added 560mL of 3mol / L hydrochloric acid solution, stirred at room temperature for 3h after stratification.The aqueous layer was extracted with dichloromethane (400 mL x 2). The organic phases were combined, the dichloromethane was evaporated under reduced pressure, 200 mL of isopropanol was added to the residue, and the mixture was stirred at 0 ° C to 10 ° C for 2 hours and then filtered. 100ml isopropanol washing cake, the wet product was dried in vacuo to give p-fluorobenzoyl acetonitrile white crystals 91.9g. Two-step reaction yield 67.7percent, purity 97.50percent. |
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