N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide | 206351-44-2

• 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: N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide
• 英文别名: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-7-oxo-1,2,3,3a,3b,4,5,5a,6,8,9,9b,10,11-tetradecahydroindeno[5,4-f]quinoline-1-carboxamide
• CAS: 206351-44-2
• 化学式: C₂₆H₃₂F₃N₃O₄
• 分子量: 507.553
• InChiKey: GLNKGBFYVCZFMR-HEVGNLSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  101.34
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide 在 苯亚硒酸酐 作用下， 以 氯苯 为溶剂， 反应 10.0h， 以41.87%的产率得到N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
  参考文献：
  名称：

  Synthesis of N-Substituted 3-Oxo-17b- carboxamide-4-aza-5a-androstanes and the Tautomerism of 3-Oxo-4-aza-5-androstenes

  摘要：

  An N-aryl-3-oxo-4-aza-5 alpha-androst-1-ene-17 beta-carboxamide and three N-aryl or alkyl substituted 17 alpha-hydroxy-3-oxo-4-aza-5 alpha -androstane-17 beta-carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17 beta-carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.

  DOI：

  10.3987/com-97-s(n)35
• 作为产物：
  描述：

  17β-[N-(3'-trifluoromethyl-4'-nitrophenyl)aminocarbonyl]-5-oxo-A-nor-3,5-secoandrostan-3-oic acid 在 甲酸 、 氨 、 potassium carbonate 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide
  参考文献：
  名称：

  Synthesis of N-Substituted 3-Oxo-17b- carboxamide-4-aza-5a-androstanes and the Tautomerism of 3-Oxo-4-aza-5-androstenes

  摘要：

  An N-aryl-3-oxo-4-aza-5 alpha-androst-1-ene-17 beta-carboxamide and three N-aryl or alkyl substituted 17 alpha-hydroxy-3-oxo-4-aza-5 alpha -androstane-17 beta-carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17 beta-carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.

  DOI：

  10.3987/com-97-s(n)35