Acetic acid (3S,5R,6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-(2-chloro-acetylamino)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester | 185842-95-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Acetic acid (3S,5R,6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-(2-chloro-acetylamino)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
• 英文别名: [(3S,5R,6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-[(2-chloroacetyl)amino]-5-hydroxy-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 185842-95-9
• 化学式: C₂₅H₃₈ClNO₅
• 分子量: 468.033
• InChiKey: FYPHNRVRLKBNCU-ZHIWKZRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,5R,6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-(2-chloro-acetylamino)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 Acetic acid (3S,5R,6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-(2-amino-acetylamino)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Steroids 54. Amino acylamidosteroids

  摘要：

  Aminosteroids were prepared and acylated with protected amino acids by means of the mixed anhydride or the active ester method. The tert-butyloxycarbonyl- (BOG) protecting group was eliminated by acidolysis, and the benzyloxycarbonyl- (Z) group by catalytic hydrogenation. 3 beta- and 6 beta-Glycylamidosteroids were prepared by indirect amination of chloroacetamido derivatives, formed by the Ritter reaction on the corresponding 3 alpha,5 alpha-cyclo and 5 alpha,6 alpha-epoxy steroids. Water-soluble double salts were produced from the compounds for pharmacological investigations. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00202-4
• 作为产物：
  描述：

  氯乙腈 、 17beta-乙酰基-5,6alpha-环氧-5alpha-雄甾烷-3beta-醇乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到Acetic acid (3S,5R,6R,8S,9S,10R,13S,14S,17S)-17-acetyl-6-(2-chloro-acetylamino)-5-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Steroids 54. Amino acylamidosteroids

  摘要：

  Aminosteroids were prepared and acylated with protected amino acids by means of the mixed anhydride or the active ester method. The tert-butyloxycarbonyl- (BOG) protecting group was eliminated by acidolysis, and the benzyloxycarbonyl- (Z) group by catalytic hydrogenation. 3 beta- and 6 beta-Glycylamidosteroids were prepared by indirect amination of chloroacetamido derivatives, formed by the Ritter reaction on the corresponding 3 alpha,5 alpha-cyclo and 5 alpha,6 alpha-epoxy steroids. Water-soluble double salts were produced from the compounds for pharmacological investigations. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00202-4