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【结 构 式】 
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【分子编号】13008 【品名】(4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(tert-Butyl)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide; 3-Oxo-4-aza-5alpha-androstane-17beta-(N-t-butylcarboxamide) 【CA登记号】98319-24-5 |
【 分 子 式 】C23H38N2O2 【 分 子 量 】374.567 【元素组成】C 73.75% H 10.23% N 7.48% O 8.54% |
合成路线1
该中间体在本合成路线中的序号：(IV)The oxidative cleavage of N-tert-butyl-3-oxo-5alpha-androst-4-ene-17beta-carboxamide (I) with NaIO4 and KMnO4 in tert butanol - aqueous Na2CO3 gives the seco-ketoacid (II), which is cyclized with liquid ammonia in ethylene glycol at 180 C to afford the DELTA5-azasteroid (III). Hydrogenation of (III) with H2 over PtO2 in acetic acid yields the corresponding saturated aza-steroid (IV), which is finally dehydrogenated with benzeneseleninic anhydride in refluxing chlorobenzene or with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and bis(trimethylsilyl)trifluoroacetamide (BSTFA) in refluxing dioxane.
| 【1】 Rasmusson, G.H.; Reynolds, G.F. (Merck & Co., Inc.); 17beta-Substd.-4-aza-5alpha-androstenones and their use as 5alpha-reductase inhibitors. AU 8539167; EP 0155096; EP 0314199; ES 8702430; JP 1985222497; JP 1989093600; US 4760071 . |
| 【2】 Rasmusson, G.H.; Reynolds, G.F. (Merck & Co., Inc.); Treatment of prostatic carcinoma with 17beta-N-monosubstd.-carbamoyl-4-aza-5-alpha-androst-1-en-3-ones. EP 0285383 . |
| 【3】 Rasmusson, G.H.; Reynolds, G.F.; Steinberg, N.G.; Walton, E.; Patel, G.F.; Liang, T.; Cascieri, M.A.; Cheung, A.H.; Brooks, J.R.; Berman, C.; Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding. J Med Chem 1986, 29, 11, 2298. |
| 【4】 Castaner, J.; Prous, J.; Finasteride. Drugs Fut 1991, 16, 11, 996. |
| 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) | 13005 | (8S,9S,10R,13S,14S,17S)-N-(tert-Butyl)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide | C24H37NO2 | 详情 | 详情 | |
| (II) | 13006 | 3-[(3S,3aS,5aS,6R,9aS,9bS)-3-[(tert-Butylamino)carbonyl]-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl]propionic acid | C23H37NO4 | 详情 | 详情 | |
| (III) | 13007 | (4aR,4bS,6aS,7S,9aS,9bS)-N-(tert-Butyl)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide | C23H36N2O2 | 详情 | 详情 | |
| (IV) | 13008 | (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(tert-Butyl)-4a,6a-dimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide; 3-Oxo-4-aza-5alpha-androstane-17beta-(N-t-butylcarboxamide) | 98319-24-5 | C23H38N2O2 | 详情 | 详情 |