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【结 构 式】

【分子编号】30079

【品名】2-chloro-N,N-diethyl-1,1,2-trifluoro-1-ethanamine; N-(2-chloro-1,1,2-trifluoroethyl)-N,N-diethylamine

【CA登记号】

【 分 子 式 】C6H11ClF3N

【 分 子 量 】189.6079896

【元素组成】C 38.01% H 5.85% Cl 18.7% F 30.06% N 7.39%

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:(XIII)

Dehydroepiandrosterone (VIII) was treated with o-phenylenephosphorochloridite (V) and then with iodine to afford iodide (IX), which was reduced to (X) by means of Zn and AcOH. Bromination of (X) with CuBr2 gave bromoketone (XI), and this was hydrolyzed to hydroxyketone (XII) upon treatment with aqueous NaOH in the presence of pyridine and oxygen. Subsequent treatment of (XII) with diethyl (2-chloro-1,1,2-trifluoroethyl)amine (XIII) afforded the target fluoroketone

1 Lewbart, M.L.; Schwartz, A.G. (Research Corporation Technologies, Inc.); Steroids useful as anti-cancer and anti-obesity agents, a therapeutic compsn. containing them and use thereof for the preparation of a therapeutic compsn.. EP 0246650; JP 1987283993 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 30072 2-chloro-1,3,2-benzodioxaphosphole 1641-40-3 C6H4ClO2P 详情 详情
(VIII) 11713 Dehydroepiandrosterone;prasterone;(3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one 53-43-0 C19H28O2 详情 详情
(IX) 30075 (3S,8R,9S,10R,13S,14S)-3-iodo-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H27IO 详情 详情
(X) 30076 (8R,9S,10R,13S,14S)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H28O 详情 详情
(XI) 30077 (8R,9S,10R,13S,14S,16R)-16-bromo-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H27BrO 详情 详情
(XII) 30078 (8R,9S,10R,13S,14S,16R)-16-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H28O2 详情 详情
(XIII) 30079 2-chloro-N,N-diethyl-1,1,2-trifluoro-1-ethanamine; N-(2-chloro-1,1,2-trifluoroethyl)-N,N-diethylamine C6H11ClF3N 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XIII)

Dehydroepiandrosterone (VIII) was first brominated with CuBr2 to give bromoketone (XIV), which was hydrolyzed to hydroxyketone (XV). After protection of (XV) as the monoacetate (XVI), fluorination at position 16 by means of (2-chloro-1,1,2-trifluoroethyl)amine (XIII) afforded fluoroketone (XVII). Ester hydrolysis in (XVI) then gave intermediate (IV).

1 Schwartz, A.G.; Lewbart, M.L.; 17-Hydroxy-steroids. US 4898694 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 30071 (3S,8R,9S,10R,13S,14S,16R)-16-fluoro-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H27FO2 详情 详情
(VIII) 11713 Dehydroepiandrosterone;prasterone;(3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one 53-43-0 C19H28O2 详情 详情
(XIII) 30079 2-chloro-N,N-diethyl-1,1,2-trifluoro-1-ethanamine; N-(2-chloro-1,1,2-trifluoroethyl)-N,N-diethylamine C6H11ClF3N 详情 详情
(XIV) 30080 (3S,8R,9S,10R,13S,14S,16R)-16-bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H27BrO2 详情 详情
(XV) 30081 (3S,8R,9S,10R,13S,14S,16R)-3,16-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H28O3 详情 详情
(XVI) 30082 (3S,8R,9S,10R,13S,14S,16R)-16-hydroxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C21H30O4 详情 详情
(XVII) 30083 (3S,8R,9S,10R,13S,14S,16R)-16-fluoro-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C21H29FO3 详情 详情
Extended Information