• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】46740

【品名】2-bromo-1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-ethanone

【CA登记号】

【 分 子 式 】C23H37BrO3

【 分 子 量 】441.44898

【元素组成】C 62.58% H 8.45% Br 18.1% O 10.87%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Regioselective addition of dimethylsulfoxonium methylide to 5-alpha-pregnane-3,20-dione (I) gave the epoxide (II). Opening of the epoxide ring of (II) with sodium methoxide produced the hydroxy ether (III). Bromination of (III) with Br2 in the presence of a catalytic amount of HBr afforded bromo ketone (IV). This was then condensed with imidazole (V) in refluxing acetonitrile to furnish the title compound.

1 Hogenkamp, D.J.; et al.; Synthesis and in vitro activity of 3beta-substituted-3alpha-hydroxypregnan-20-ones: Allosteric modulators of the GABAA receptor. J Med Chem 1997, 40, 1, 61.
2 Hogenkamp, D.L. (CoCensys, Inc.); 3alpha-Hydroxy-3beta methoxymethyl-21-heterocycle substd. steroids with anesthetic activity. WO 0066614 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 46737 (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one 566-65-4 C21H32O2 详情 详情
(II) 46738   C22H34O2 详情 详情
(III) 46739 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-ethanone C23H38O3 详情 详情
(IV) 46740 2-bromo-1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-ethanone C23H37BrO3 详情 详情
(V) 10255 Imidazole; 1H-Imidazole 288-32-4 C3H4N2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

Regioselective addition of dimethylsulfoxonium methylide to 5-alpha-pregnane-3,20-dione (I) gave the epoxide (II). Opening of the epoxide ring of (II) with sodium methoxide produced the hydroxy ether (III). Bromination of (III) with Br2 in the presence of a catalytic amount of HBr afforded bromo ketone (IV). This was then condensed with 6-hydroxyquinoline (V) in the presence of potassium tert-butoxide to furnish the quinolinyl ether (VI). The quinoline ring was then oxidized with m-chloroperbenzoic acid, yielding the title N-oxide.

1 Hogenkamp, D.J.; et al.; Synthesis and in vitro activity of 3beta-substituted-3alpha-hydroxypregnan-20-ones: Allosteric modulators of the GABAA receptor. J Med Chem 1997, 40, 1, 61.
2 Hogenkamp, D.L. (CoCensys, Inc.); 3alpha-Hydroxy-3beta methoxymethyl-21-heterocycle substd. steroids with anesthetic activity. WO 0066614 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 46737 (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one 566-65-4 C21H32O2 详情 详情
(II) 46738   C22H34O2 详情 详情
(III) 46739 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-ethanone C23H38O3 详情 详情
(IV) 46740 2-bromo-1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-ethanone C23H37BrO3 详情 详情
(V) 46742 6-Hydroxyquinoline; 6-quinolinol 580-16-5 C9H7NO 详情 详情
(VI) 46741 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-(6-quinolinyloxy)-1-ethanone C32H43NO4 详情 详情
Extended Information