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CAS No. : | 191014-55-8 | MDL No. : | MFCD04116335 |
Formula : | C8H6FNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HGBKZVIQHCUHRI-UHFFFAOYSA-N |
M.W : | 151.14 | Pubchem ID : | 2783329 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 37.61 |
TPSA : | 33.02 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) : | -5.43 cm/s |
Log Po/w (iLOGP) : | 1.9 |
Log Po/w (XLOGP3) : | 2.53 |
Log Po/w (WLOGP) : | 2.13 |
Log Po/w (MLOGP) : | 1.55 |
Log Po/w (SILICOS-IT) : | 2.21 |
Consensus Log Po/w : | 2.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.71 |
Solubility : | 0.296 mg/ml ; 0.00196 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.87 |
Solubility : | 0.204 mg/ml ; 0.00135 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.87 |
Solubility : | 0.203 mg/ml ; 0.00134 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313 | UN#: | |
Hazard Statements: | H302-H312-H319-H332 | Packing Group: | |
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 |
---|---|---|
95% | With aluminum (III) chloride In toluene at 130℃; for 18 h; | A mixture of intermediate 127, 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C. for 18 hrs. After cooling, ice water (~50 mL) was added and the resulting mixture extracted with ether (20 mLx2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: 1H NMR (DMSO-d6, 300 MHz) ? ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) ? ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199. |
95% | Stage #1: With aluminum (III) chloride In toluene at 130℃; for 18 h; Stage #2: With water In toluene |
A mixture of 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130° C. for 18 hrs. After cooling, ice water (50 mL)was added and the resulting mixture extracted with ether (20 mL.x.2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) δ ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84,161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199. |
95% | Stage #1: With aluminum (III) chloride In toluene at 130℃; for 18 h; Stage #2: With water In toluene at 0℃; |
4-Fluoro-2-hydroxyben.sum.onitrile. A mixture of intermediate 127, 4-fluoro-2- methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 °C for 18 hrs. After cooling, ice water (~50 mL)was added and the resulting mixture extracted with ether (20 mL x 2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (IH, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (IH, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) δ ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35.HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | at 180℃; for 5.5 h; | To a solution of intermediate 126, 1-bromo-4-fluoro-2-methoxybenzene (9.0 g) in N-methylpyrrolidone (100 mL, Sure Seal; Aldrich) was added CuCN (6.6 g, 73.7 mmol, 1.8 eq.; Aldrich), and the mixture stirred at 180 C. under anhydrous nitrogen for 5.5 hrs. After cooling, 14percent aqueous NH4OH (330 mL) was added and stirring continued for 45 min at room temperature. The mixture was extracted with ether (100 mLx3), and the combined extracts washed sequentially with dilute aqueous NH4OH, dilute HCl and brine, then dried (MgSO4), and concentrated to provide the title compound (5.2 g, Yield 85percent in 2 steps) as a white solid: 1H NMR (CDCl3, 500 MHz) ? ppm: 3.91 (3H, s, OMe), 6.69 (1H, dd, J=2.3 Hz, J=10.5 Hz, Ar-H), 6.72 (1H, dt, J=2.5 Hz, J=J=8.0 Hz, Ar-H), 7.55 (1H, dd, J=6.5 Hz, J=8.5 Hz, Ar-H); 13C NMR (CDCl3, 125.8 Hz) ? ppm: 56.49, 98.16, 100.06, 100.27, 108.31, 108.50, 115.83 135.37, 135.46, 163.25, 163.34 165.47, 167.50. An analytical sample was obtained by trituration with ether: Anal. calcd for C8H6FNO: C, 63.57; H, 4.00; N, 9.26; found: C, 63.36; H, 3.91; N, 9.16. |
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