N-(3'-trifluoromethyl-4'-nitrophenyl)-17α-hydroxy-3-oxoandrost-4-ene-17β-carboxamide | 206351-45-3

• 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)-17α-hydroxy-3-oxoandrost-4-ene-17β-carboxamide
• 英文别名: (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
• CAS: 206351-45-3
• 化学式: C₂₇H₃₁F₃N₂O₅
• 分子量: 520.549
• InChiKey: VHELHMHTYNYDPR-COJLFNMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  109.54
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(3'-trifluoromethyl-4'-nitrophenyl)-17α-hydroxy-3-oxoandrost-4-ene-17β-carboxamide 在 palladium on activated charcoal 乙酸铵 、 potassium permanganate 、 sodium periodate 、 氢气 、 sodium carbonate 作用下， 以 水 、 溶剂黄146 、 叔丁醇 为溶剂， 40.0~50.0 ℃ 、1.0 MPa 条件下， 反应 13.08h， 生成 N-(3'-trifluoromethyl-4'-aminophenyl)-17α-hydroxy-3-oxo-4-azaandrost-5-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：

  表雄酮 在 氯化亚砜 、 硫酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 吡啶 、 水 、 甲苯 为溶剂， 反应 25.67h， 生成 N-(3'-trifluoromethyl-4'-nitrophenyl)-17α-hydroxy-3-oxoandrost-4-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