(8S,9S,10R,13S,14S,17S)-3-Bromo-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methoxy-methyl-amide | 228117-43-9

• 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: (8S,9S,10R,13S,14S,17S)-3-Bromo-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methoxy-methyl-amide
• 英文别名: (8S,9S,10R,13S,14S,17S)-3-bromo-N-methoxy-N,10,13-trimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
• CAS: 228117-43-9
• 化学式: C₂₂H₃₂BrNO₂
• 分子量: 422.406
• InChiKey: ALCAEJGKUKNRES-XUCMERPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8S,9S,10R,13S,14S,17S)-3-Bromo-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methoxy-methyl-amide 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 calcium diformate 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 SB 209963
  参考文献：
  名称：

  Synthesis of 3-carboxy-20-keto steroid, SB 209963, a 5α-reductase inhibitor, by palladium-catalyzed hydroxycarbonylation

  摘要：

  SE 209963 was produced in three steps starting from 17 beta-carboxyandrost-4-en-3-one. A palladium-catalyzed hydroxycarbonylation introduced the carboxylic acid under mild conditions without epimerization at C-17. This reaction represents the first example of hydroxycarbonylation of a vinyl halide under neutral conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00456-6
• 作为产物：
  描述：

  3-氧代-雄甾-4-烯-17beta-羧酸 在 吡啶 、 草酰溴 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 (8S,9S,10R,13S,14S,17S)-3-Bromo-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methoxy-methyl-amide
  参考文献：
  名称：

  Synthesis of 3-carboxy-20-keto steroid, SB 209963, a 5α-reductase inhibitor, by palladium-catalyzed hydroxycarbonylation

  摘要：

  SE 209963 was produced in three steps starting from 17 beta-carboxyandrost-4-en-3-one. A palladium-catalyzed hydroxycarbonylation introduced the carboxylic acid under mild conditions without epimerization at C-17. This reaction represents the first example of hydroxycarbonylation of a vinyl halide under neutral conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00456-6