N-tert-butyl-3-<<(trifluoromethyl)sulfonyl>oxy>estra-1,3,5(10),16-tetraene-17-carboxamide | 124651-18-9

• 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: N-tert-butyl-3-<<(trifluoromethyl)sulfonyl>oxy>estra-1,3,5(10),16-tetraene-17-carboxamide
• 英文别名: [(8S,9S,13S,14S)-17-(tert-butylcarbamoyl)-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-yl] trifluoromethanesulfonate
• CAS: 124651-18-9
• 化学式: C₂₄H₃₀F₃NO₄S
• 分子量: 485.568
• InChiKey: JOAIBIKOPLLVTM-GBPOLFSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-3-<<(trifluoromethyl)sulfonyl>oxy>estra-1,3,5(10),16-tetraene-17-carboxamide 在 platinum(IV) oxide palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 3-(methoxycarbonyl)estra-1,3,5(10)-triene-17β-carboxylic acid tert-butylamide
  参考文献：
  名称：

  Steroidal A ring aryl carboxylic acids: a new class of steroid 5.alpha.-reductase inhibitors

  摘要：

  A series of 17 beta-carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids has been prepared and evaluated in vitro as inhibitors of human and rat prostatic steroid 5 alpha-reductase (EC 1.3.1.30). Potent inhibition of the human enzyme, in particular, was observed and preliminary studies using rat enzyme suggest that the inhibition results from the formation of an enzyme-NADP(+)-inhibitor complex. The compounds were synthesized from estrone, generally employing a differentiated bis-triflate carbonylation strategy.

  DOI：

  10.1021/jm00165a009
• 作为产物：
  描述：

  雌酚酮 在 palladium diacetate 、 2,6-二叔丁基-4-甲基吡啶 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 N-tert-butyl-3-<<(trifluoromethyl)sulfonyl>oxy>estra-1,3,5(10),16-tetraene-17-carboxamide
  参考文献：
  名称：

  Steroidal A ring aryl carboxylic acids: a new class of steroid 5.alpha.-reductase inhibitors

  摘要：

  A series of 17 beta-carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids has been prepared and evaluated in vitro as inhibitors of human and rat prostatic steroid 5 alpha-reductase (EC 1.3.1.30). Potent inhibition of the human enzyme, in particular, was observed and preliminary studies using rat enzyme suggest that the inhibition results from the formation of an enzyme-NADP(+)-inhibitor complex. The compounds were synthesized from estrone, generally employing a differentiated bis-triflate carbonylation strategy.

  DOI：

  10.1021/jm00165a009