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去氧孕烯
CAS号 54024-22-5
中文别名 去氧孕烯;13β-乙基-11-次甲基-18,19-双失碳孕甾-4-烯-20炔基-17β-醇;13-乙基-11-亚甲基-18,19-双失碳孕甾-4-烯-20-炔基-17-醇;待索盖斯著;地索高诺酮;地索睾诺酮;(17Α)-13-乙基-11-亚甲基-18,19-二去甲孕甾-4-烯-20-炔-17-醇;去氧孕烯(低索高诺酮)
英文别名 13-ethyl-11-methylene-19-dinorpregn-4-en-20-yn-17-o(17-alpha)-1;org2969;13-ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol;DESOGESTREL;(17a)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol;Cerazette;Cyclosa;Dicromil
分子量 310.473
分子式 C22H30O
EINECS编号 258-929-4
综合信息 查看供应
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SMILES

C#C[C@@]1(O)[C@]2(CC)[C@@H](CC1)[C@H]3[C@@H]([C@@H]4C(=CCCC4)CC3)C(=C)C2


去氧孕烯 性质

熔点 109-110°C

储存条件 -20°C Freezer

去氧孕烯化学性质 

结晶,熔点109~110℃。[α]D20+55°(氯仿)。

 去氧孕烯用途

孕激素避孕药,抗雌性激素的活性很强,能抑制排卵及促性腺激素的分泌。用于防止妊娠。
为强效排卵抑制剂,尚能改变宫颈粘液稠度、抑制子宫内膜发育

去氧孕烯生产方法

化合物(Ⅰ)先氧化11位的羟基为酮后,再进行Wittig反应,然后脱缩酮,得到化合物(Ⅲ)。(Ⅲ)和乙二硫醇反应,在3位形成硫缩酮,接着硼氢化钠还原17位羰基为羟基,再在液氨中和钠作用,脱去3位的硫缩酮,得到化合物(Ⅶ)。把17位的羟基重新氧化为羰基,最后和乙炔钾反应,得到去氧孕烯。

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风险术语
上游原料
1,2-ethanedithiol(1S,7aS)-7a-ethyl-1-hydroxy-1,2,3,6,7,7a-hexahydro-5H-inden-5-one(1S,7aS)-1-[[tert-butyl(dimethyl)silyl]oxy]-7a-ethyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one(1S,3aS,7aS)-1-[[tert-butyl(dimethyl)silyl]oxy]-7a-ethyloctahydro-5H-inden-5-onemethyl (3S,3aS,7aS)-3-[[tert-butyl(dimethyl)silyl]oxy]-3a-ethyl-6-hydroxy-2,3,3a,4,7,7a-hexahydro-1H-indene-5-carboxylate1-(2-iodoethyl)-3-methoxybenzene; 3-(2-iodoethyl)phenyl methyl ethermethyl (3S,3aS,7S,7aS)-3-[[tert-butyl(dimethyl)silyl]oxy]-3a-ethyl-6-hydroxy-7-(3-methoxyphenethyl)-2,3,3a,4,7,7a-hexahydro-1H-indene-5-carboxylatemethyl (8S,13S,14S,17S)-13-ethyl-17-hydroxy-3-methoxy-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-11-carboxylatemethyl (8S,13S,14S,17S)-17-[[tert-butyl(dimethyl)silyl]oxy]-13-ethyl-3-methoxy-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-11-carboxylate((8S,13S,14S,17S)-17-[[tert-butyl(dimethyl)silyl]oxy]-13-ethyl-3-methoxy-7,8,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-11-yl)methanoltert-butyl(dimethyl)silyl (8R,9R,13S,14S,17S)-13-ethyl-3-methoxy-11-methylene-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ether; tert-butyl[[(8R,9R,13S,14S,17S)-13-ethyl-3-methoxy-11-methylene-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl]oxy]dimethylsilane(8R,9S,10R,13S,14S,17S)-13-ethyl-17-hydroxy-11-methylene-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (8R,9S,10R,13S,14S,17S)-13-ethyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol(8R,9S,10R,13S,14S)-13-ethyl-11-methylene-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-onedichloro(ethynyl)cerium1,2-ethanedithiol(8R,9S,10R,13S,14S)-13-ethyl-11-methylene-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione(8R,9S,10R,13S,14S)-13-ethyl-11-methylene-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one