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CAS No. : | 4491-33-2 | MDL No. : | MFCD02149441 |
Formula : | C12H11NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PWOYTBYNBYNZCO-UHFFFAOYSA-N |
M.W : | 201.22 | Pubchem ID : | 421739 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.83 |
TPSA : | 39.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.01 cm/s |
Log Po/w (iLOGP) : | 2.47 |
Log Po/w (XLOGP3) : | 3.54 |
Log Po/w (WLOGP) : | 2.41 |
Log Po/w (MLOGP) : | 1.91 |
Log Po/w (SILICOS-IT) : | 2.65 |
Consensus Log Po/w : | 2.6 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.049 mg/ml ; 0.000244 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.05 |
Solubility : | 0.018 mg/ml ; 0.0000896 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.19 |
Solubility : | 0.0131 mg/ml ; 0.000065 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.74 |
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 |
---|---|---|
100% | With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 18 h; Inert atmosphere | A mixture of quinaldine acid (5) (2.0 g, 11.55 mmol), dried K2CO3 (3.19 g, 23.10 mmol) and anhydrous DMF (24 mL) was stirred until the reagents had been dissolved under an argon atmosphere. Iodoethane (2.77 mL, 34.65 mmol) was added and stirred for 18 h to 60 °C. A 30percent cooled aqueous solution of HCl (30 mL) was added. The medium was neutralized with a saturated solution of NaHCO3 until the gas formation was ceased. Extraction was carried out with ethyl acetate (3x 60 mL). The combined organic phases were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography by eluting with hexane/AcOEt (8:2) to furnish ester 6 as a translucent oil in quantitative yield. Rf 0.51 (hexane/AcOEt 7:3). IR (neat) νmax/cm-1: 3061, 2982, 2938, 2904, 1714, 1463, 1368, 1312, 1133, 1103, 1016, 844, 774. 1H NMR (400 MHz, CDCl3) δ 7.96-7.94 (m, 1H), 7.85-7.81 (m, 1H), 7.76-7.73 (m, 1H), 7.42-7.36 (m, 2H), 7.22-7.18 (m, 1H), 4.22-4.17 (m, 2H), 1.14-1.10 (m, 3H). 13C NMR (100 MHz, CDCl3) δ 164.9, 147.9, 147.2, 136.8, 130.3, 129.8, 128.9, 128.1, 127.2, 120.6, 61.7, 14.1. HRMS (ESI+) calcd for C12H11NO2 [M+H]+ 202.0868, found 202.0868. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | at 80℃; for 6 h; | 60.0 mg (0.3 mmol) of ethyl 4,4-diethoxy-2-butenoate obtained in the step (2) and 28.0 mg (0.3 mmol) of aniline dissolved in 1 mL of acetic acid in a reactor equipped with magnetic stirring. ,The mixture was stirred and reacted at 80 ° C for 6 h.The TCL stops the heating after detecting the reaction. The product and the starting material were separated by preparative thin layer chromatography (PTLC). The eluent was a mixture of petroleum ether and ethyl acetate in a volume ratio of 6:1.Finally, 40.0 mg (0.2 mmol) of the ethyl quinolin-2-carboxylate was obtained. |
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