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CAS No. : | 135631-90-2 | MDL No. : | MFCD00795100 |
Formula : | C11H12BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FTRFIBKHXWYJAW-UHFFFAOYSA-N |
M.W : | 254.12 | Pubchem ID : | 10729589 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 63.74 |
TPSA : | 29.1 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.98 cm/s |
Log Po/w (iLOGP) : | 2.29 |
Log Po/w (XLOGP3) : | 2.63 |
Log Po/w (WLOGP) : | 2.5 |
Log Po/w (MLOGP) : | 2.73 |
Log Po/w (SILICOS-IT) : | 3.23 |
Consensus Log Po/w : | 2.68 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.39 |
Solubility : | 0.104 mg/ml ; 0.000408 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.89 |
Solubility : | 0.326 mg/ml ; 0.00128 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.79 |
Solubility : | 0.00415 mg/ml ; 0.0000163 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.85 |
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 |
---|---|---|
90% | With aluminum (III) chloride In dichloromethane at 20℃; for 2.5 h; Inert atmosphere | General procedure: To a solution of 4-bromoaniline (5.0 g, 29.1 mmol) in DCM (100 mL) was added 3,3-dimethylacryloyl chloride (3.40 mL, 30.6 mmol) and the resultant white suspension was stirred for 0.5 h, after which pyridine (9.70 mL, 30.6 mmol) was added and the solution stirred at rt for 16 h. The solution was diluted with DCM and H2O, washed with sat. NH4Cl, H2O, dried (MgSO4) and evaporated to give a crude light brown solid (33 g) which was recrystallised from hexane to give N-(4-bromophenyl)-3-methylbut-2-enamide as a white solid (6.87 g, 94percent). N-(4-Bromophenyl)-3-methylbut-2-enamide (4.5 g, 17.7 mmol) and AlCl3 (3.54 g, 26.6 mmol) were added to anhydrous DCM (90 mL) under Ar and the resultant solution stirred vigorously for 2.5 h at rt. The reaction was then cooled to 0 °C, quenched slowly with H2O, diluted with DCM, stirred with 20percent NaOH (w/v) until the solution turned off-white, then further washed with H2O, dried (MgSO4) and evaporated to give 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-2-one (4.07 g, 90percent). To a solution of 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-2-one (4.07 g, 16.02 mmol) in anhydrous DMF (50 mL) was added crushed KOH (2.70 g, 48.06 mmol) and the resultant slurry stirred for 1 h at 50 °C under Ar. To this was added 2-iodopropane (4.8 mL, 48.06 mmol) and the solution stirred at 50 °C for 40 h. The reaction was quenched with H2O, diluted with EtOAc, washed with sat. NH4Cl, H2O and brine, dried (MgSO4) and evaporated to give a crude clear oil. This was purified by SiO2 chromatography (hexane/EtOAc 9:1, with 1percent Et3N as eluent) to give 6-bromo-4,4-dimethyl-1-(propan-2-yl)-1,2,3,4-tetrahydroquinolin-2-one as a colourless oil (2.19 g, 46percent):1H NMR (700 MHz; CDCl3) δ 1.27 (s, 6H), 1.51 (d, J = 7.0 Hz, 6H), 2.40 (s, 2H), 4.68 (sept, J = 7.1 Hz, 1H), 7.00 (d, J = 8.7 Hz, 1H), 7.32 (dd, J = 8.7, 2.3 Hz, 1H), 7.36 (d, J = 2.3 Hz, 1H); 13C NMR (176 MHz; CDCl3) δ 20.4, 26.8, 33.2, 47.2, 48.9, 116.4, 118.6, 127.6, 129.9, 138.6, 138.9, 169.8; IR (neat) max/cm–12964m, 2934w, 2872w, 1671s, 1590m, 1484s, 1417m, 1332s, 1253s, 811s; MS (ES): m/z = 296.4 [M+H]+; HRMS (ES) calcd. for C14H19NOBr [M+H]+: 296.0650, found: 296.0658. |
68% | at 80 - 130℃; for 1.5 h; | Aluminum chloride (5 g, 37.5 mmol) was added portionwise to N-(4-bromophenyl)-3-methylbut-2-enoic amide (Compound 26, 7.69 g, 30.0 mmol) in a 500 mL beaker at 130° C. over 1 h. The beaker was then cooled to 80° C. and another portion of aluminum chloride (1 g, 7.5 mmol) was added. After stirring at 80° C. for 0.5 h, the beaker was cooled with an ice-bath and ice was added slowly into the mixture. The resulting slurry was then extracted with ether (3*10 mL). The combined organic layer was washed with brine (1*10 mL), saturated NaHCO3 (1*10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (75:25 hexane/ethyl acetate) gave the title compound (5.20 g, 68percent yield) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.40 (d, J=2.4 Hz, 1H), 7.31-7.27 (m, 2H), 6.65 (bs, 1H), 2.47 (s, 2H), 1.32 (s, 6H). |
68% | at 80 - 130℃; for 1.5 h; | 6-Bromo-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (Intermediate 4) Aluminum chloride (5 g, 37.5 mmol) was added portionwise into N-(4-bromophenyl)-3-methylbut-2-enoic amide (Intermediate 3, 7.69 g, 30.0 mmol) in a 500 mL beaker at 130° C. over 1 h. The beaker was then cooled to 80° C. and another portion of aluminum chloride (1 g, 7.5 mmol) was added. After stirring at 80° C. for 0.5 h, the beaker was cooled with an ice-bath and ice was added slowly into the mixture. The resulting slurry was then extracted with ether (3*10 mL). The combined organic layer was washed with brine (1*10 mL), saturated NaHCO3 (1*10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chomatography (75:25 hexane/ethyl acetate) yielded the title compound as a pale yellow solid (5.20 g, 68percent yield). |
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