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CAS No. : | 138716-20-8 | MDL No. : | MFCD00111509 |
Formula : | C11H12FNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 193.22 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 53.44 |
TPSA : | 20.31 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) : | -6.01 cm/s |
Log Po/w (iLOGP) : | 2.32 |
Log Po/w (XLOGP3) : | 2.07 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 2.09 |
Log Po/w (SILICOS-IT) : | 2.23 |
Consensus Log Po/w : | 2.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.46 |
Solubility : | 0.668 mg/ml ; 0.00346 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.13 |
Solubility : | 1.45 mg/ml ; 0.00749 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.83 |
Solubility : | 0.286 mg/ml ; 0.00148 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
20% | With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In ethanol Reflux; | |
95% | In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 48h; | General experimental procedure for synthesis of Enaminones (5) General procedure: To a solution of acetophenone (1 mmol) in dry xylene (5 ml), was added a solution of DMF-DMA (2 mmol) and refluxed for 48h at 120°C. After cooling, the solvent was evaporated and residue was extracted with ethyl acetate (3x20ml). The combined organic layer was concentrated in vacuo and purified by recrystallisation with diethyl ether. |
93% | With <i>L</i>-proline In neat (no solvent) at 80℃; for 1h; |
90% | With guanidineacetic acid at 100℃; for 1h; | |
88% | In toluene at 110℃; Inert atmosphere; | |
88% | In toluene at 110℃; | |
88% | In toluene at 110℃; | |
88% | In toluene at 110℃; Inert atmosphere; | |
88% | In toluene at 110℃; | |
76% | In ethanol for 6h; Reflux; | The acetophenone (25 mmol) was solved in ethanol (20 mL) and N,N-dimethylformamide dimethyl acetal (37 mmol) was added. The reaction mixture was stirred under reflux for 6 h and concentrated. The residue was elutriated in hexane and the remaining precipitate was filtered off, washed several times with hexane and dried.Intermediate B1: (E)-3-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one Yield: 76%1H-NMR (300 MHz, d6-DMSO): α=7.92 (m, 2H), 7.67 (d, 1H), 7.20 (m, 2H), 5.77 (d, 1H), 3.10 (bs, 3H), 2.87 (br s, 3H) ppm. |
70% | With boron trifluoride diethyl ether complex In toluene at 110℃; for 24h; | |
for 14h; Heating; | ||
In N,N-dimethyl-formamide | ||
at 120℃; for 16h; | ||
In 5,5-dimethyl-1,3-cyclohexadiene Reflux; | General procedure for synthesis of substituted (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one 2 (a-u) General procedure: To the appropriate methyl ketones 1 (a-u) (0.01 mol) in round-bottom flask, DMF-DMA (N,N-Dimethylformamide dimethyl acetal) was added and refluxed in xylene for the appropriate time. The solvent was evaporated in vacuum and the residual solid was crystallized from ethanol to afford corresponding pure product 2. | |
at 110℃; for 0.166667h; Microwave irradiation; | 1 Synthesis of 1-(4-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one (3) To a solution of p-fluoroacetophenone (1) (10 mmol) in xylene or without solvent was added dimethylformamide-dimethylacetal (DMF-DMA) (12 mmol) and the mixture was mixed in a HP-500 Plus process vessel. The vessel was capped properly and irradiated by microwaves under pressurized conditions (17.2 bar, 110 °C) for 10 min. The excess DMF-DMA was evaporated in vacuo and the residue was dissolved in ether (50 mL) and dried over MgSO4. After evaporation of the solvent the resulting solid was recrystallized from hexane to afford (E)-1-(4-fluorophenyl)-3-(dimethylamino)prop-2-en-1-one (2), The physical and spectral data of the synthesized compound are listed below. Mp.: 64-65 °C; IR (KBr) cm-1: 1664 (C=O), 1598 (C=N); 1H NMR (CDCl3): δ 3.02 (s, 6H, N(CH3)2), 5.67 (d, 1H, J = 12.3 Hz, -CO-CH]), 7.10 (d, 2H, Ar-H), 7.80 (d, J = 12.3 Hz, 1H, =CH-N), 7.92 (d, 2H, Ar-H).; MS (m/z): 193 (M+); C11H12FNO:Anal. Calcd: C, 68.38; H, 6.26; N, 7.25. Found C, 68.28; H, 6.16; N, 7.35. %. | |
In toluene at 110℃; Inert atmosphere; | ||
In toluene at 110℃; | ||
for 2h; Reflux; | 41 A mixture of 1-(4-fluorophenyl)ethanone (2 g) and 1,1-dimethoxy-N,N-dimethylmethanamine (4 ml) was refluxed for 2 h. The solvent was removed. To the residue was added hexane to give the title compound as crystals (889 mg).1H-NMR (300 MHz, DMSO-d6) δ: 2.92 (3H, s), 3.14 (3H, s), 5.82 (1H, d, J=12.2 Hz), 7.24 (2H, m), 7.71 (1H, d, J=12.2 Hz), 7.96 (2H, dd, J=8.9, 5.7 Hz). | |
In 5,5-dimethyl-1,3-cyclohexadiene for 7h; Reflux; | (1) Preparation of N,N-dimethylenaminones General procedure: The N,N-dimethylenaminones were synthesized according to literature method with slight modifications. 1 To a solution of ketones (1.54 g, 12.8 mmol) in xylene (15 mL) was added N,N-dimethylformamide dimethylacetal (3.6 mL, 25.7 mmol) and refluxed for 7 h (monitored by TLC). Xylene was then removed by distillation and crude residue was purified by column chromatography (silica gel; hexane-EtOAc = 3:7) to yield (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one ( 1 ) as a pure light yellow solid. | |
In acetonitrile at 82℃; for 1h; Microwave irradiation; Sealed tube; | Synthesis of compounds 7a-m General procedure: A vial containing a mixture of aromatic ketone 13a-m (1 mmol) and N,N-dimethylformamide dimethyl acetal (12) (1 mmol) in CH3CN (3 mL) was sealed and placed in a Anton Paar Microwave Synthetic Reactor. The vial was subjected to microwave irradiation, programmed at 82 oC and 150W. After a period of 30 second, the temperature reached a plauteau, 82 oC, and remained constant. After stirring reaction for 60 min, 2-hydroxy-1,4-naphthoquinone (15) (1 mmol) and glacial AcOH (0.2 mmol) were added into the vial. The reaction was stirred for a further 30 min. The vial was then cooled to room temperature. Evaporation of the solvent gave crude products 7a-m, which was purified by column chromatography using a MeOH-EtOAc-DCM eluent (1:4:5) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With toluene-4-sulfonic acid In methanol at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With ammonium acetate In ethanol for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With gallium(III) iodide; ammonium acetate In neat (no solvent) at 80℃; for 1h; | |
82% | With anhydrous ammonium acetate; Montmorillonite K10 In isopropanol Heating; | |
With ammonium acetate; glacial acetic acid Reflux; | General procedure for synthesis of ethyl 2-methyl-6- substituted phenylnicotinate 3 (a-u) General procedure: To a above synthesized solution of the appropriate enaminone 2 (a-u) (1 mmol) in glacial acetic acid (15 mL), ethyl acetoacetate (1.5 mmol) and ammonium acetate (40 mmol) were added. The reaction mixture was heated under reflux for 5-8 h. After cooling and pouring into ice-water, the residue obtained was filtered and washed with petroleum ether then with water and finally crystallized from ethanol to yield the desired product 3 (a-u). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (E)-3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one With trichlorophosphate Stage #2: With water In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.64% | In acetic acid at 120℃; for 0.333333h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.56% | In acetic acid at 120℃; for 0.333333h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: POCl3 1.2: H2O / tetrahydrofuran 2.1: acetonitrile / 20 °C 2.2: 80 percent / NaPF6 / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 34 percent / p-TsOH / methanol / 0.5 h / 20 °C 2: 44 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; sodium cyanoborohydride; trichlorophosphate In diethyl ether; chloroform; isopropyl alcohol | 40 EXAMPLE 40 EXAMPLE 40 By using a method similar to that described in Example 35, but starting from 1-(4-fluorophenyl)-3-dimethylamino-2-propen-1-one (10 g), phosphorus oxychloride (4.76 cc), thiophenol (5.57 cc) and sodium cyanoborohydride (1.92 g), a residue is obtained which is taken up in chloroform. The solution is then adjusted to pH 10 by adding a concentrated aqueous solution of sodium hydroxide. The organic phase is separated and then the aqueous phase is extracted with methylene chloride. The organic phases are collected, dried over sodium sulphate, filtered and then evaporated to dryness under reduced pressure (2.7 kPa) at 30° C. A residue is obtained which is dissolved in isopropanol (30 cc). A 3N solution (12 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The solid which precipitates is separated off by filtration and recrystallized from isopropanol (30 cc). In this way 1-dimethylamino-3-(4-fluorophenyl)-3-phenylthio-2-propene (E) hydrochloride (3.3 g) is obtained in the form of a white solid melting at 160° C. 1-(4-Fluorophenyl)-3-dimethylamino-2-propen-1-one can be obtained by using the method described by H. Meerwein, W. Florian, N. Schon and G. Stopp, Ann. Chem. 641, 1, (1961). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal In hexane | 48 3-Dimethylamino-4'-fluoroacrylophenone EXAMPLE 48 3-Dimethylamino-4'-fluoroacrylophenone A mixture of 5.0 g. of p-fluoroacetophenone and 10 ml. of dimethylformamide dimethylacetal is refluxed for 4 hours. Evaporation gives an oil which crystallizes with the addition of hexane to give the product, m.p. 83.5°-84° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | at 120℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With hydroxylamine hydrochloride In methanol at 65℃; for 2.5h; | |
70% | With hydroxylamine hydrochloride In ethanol at 78℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With pyridine In dichloromethane at 40℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With pyridine In dichloromethane at 40℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 9% 2: 54% | With pyridine; hydroxylamine hydrochloride In ethanol at 78℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol for 4h; Reflux; | 42 A mixture of (2E)-3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one (800 mg) and methylhydrazine (257 μl) in ethanol was refluxed for 4 h. The solvent was removed, and the residue was chromatographed on basic silica gel using hexane/ethyl acetate as an eluent to give the title compound (592 mg).1H-NMR (300 MHz, DMSO-d6) δ: 3.83 (3H, s), 6.39 (1H, d, J=1.9 Hz), 7.34 (2H, dd), 7.46 (1H, d, J=1.5 Hz), 7.58 (2H, dd, J=8.9, 5.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With Tris(trimethylsilyl)phosphane; cesium fluoride In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With cesium fluoride In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: sodium ethanolate / ethanol / 70 °C 2: sulfuric acid; dihydrogen peroxide; ferrous(II) sulfate heptahydrate / 0 - 15 °C 3: sulfuric acid / 100 °C 4: thionyl chloride / 6 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium ethanolate In ethanol at 70℃; | 5.4. General procedure for the preparation of 4-substititedphenylpyrimidines (21a-d) General procedure: To the mixture of formamidine acetate (9.9g, 0.096mol), sodium ethoxide (10.9g, 0.16mol) and anhydrous EtOH (300mL), an appropriate (E)-3-(dimethylamino)-1-substititedphenylprop-2-en-1-one (0.08mol) was added slowly at 70°C. Upon the completion of addition, the reaction mixture then was stirred at reflux for 15-20h and monitored by TLC. The solvent was concentrated in vacuum and the residue was resolved with dichloromethane (300mL), washed with water (30mL×3), brine (60mL), dried over anhydrous Na2SO4, and concentrated in vacuum to give the corresponding 4-substititedphenylpyrimidines as light yellow solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In N,N-dimethyl acetamide; toluene at 110℃; Inert atmosphere; | |
84% | In dimethyl amine at 80℃; | 5.4.General procedure for the preparation of (E)-3-(dimethylamino)-1-substititedphenylprop-2-en-1-ones (20a-d) General procedure: A mixture of an appropriate substituted acetophenone (0.1mol) and DMF-DMA (39.8mL, 0.3mol) was heated at 80°C for 8-12h and monitored by TLC. Upon cooling to room temperature of the reaction mixture, Et2O (40mL) and petroleum ether (120mL) were added and stirred for 0.5h, and then the precipitatewas collected by filtration and dried to give the corresponding (E)-3-(dimethylamino)-1-substititedphenylprop-2-en-1-one as yellow solids. |
71% | With 1,1-dimethoxyethane In toluene for 4h; Reflux; | 342.2 Step 2. Synthesis of (2E)-3-(Dimethylamino)-1-(4-fluorophenyl)-2-propen-1-one Step 2. Synthesis of (2E)-3-(Dimethylamino)-1-(4-fluorophenyl)-2-propen-1-one A solution of 1-(4-fluorophenyl)ethanone (0.875 mL, 7.24 mmol) in toluene (5.0 mL) and N,N-dimethylformamide dimethyl acetal (DIFDA, 1.35 mL, 10.1 mmol) were used to carry out the reaction. After the reaction was reflux for 4 h and work-up, the residue was purified by Isco Combi-Flash Companion column chromatography (0-60% ethyl acetate in n-hexane) to give (2E)-3-(dimethylamino)-1-(4-fluorophenyl)-2-propen-1-one (0.987 g, 71%). 1H NMR (CDCl3, 400 MHz) δ 7.91 (dd, 2H), 7.80 (d, 1H), 7.07 (dd, 2H), 5.67 (d, 1H), 3.15 (br s, 3H), 2.93 (br s, 3H). |
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