(8R,9S,13S,14S,17S)-17-(Dimethyl-propyl-silanylethynyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | 107149-31-5

• 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: (8R,9S,13S,14S,17S)-17-(Dimethyl-propyl-silanylethynyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• 英文别名: (8R,9S,13S,14S,17S)-17-[2-[dimethyl(propyl)silyl]ethynyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 107149-31-5
• 化学式: C₂₅H₃₆O₂Si
• 分子量: 396.645
• InChiKey: PWAHDXCIAAJEGM-WJGLBBAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Dimethyl-[(8R,9S,13S,14S,17S)-13-methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ylethynyl]-propyl-silane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (8R,9S,13S,14S,17S)-17-(Dimethyl-propyl-silanylethynyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  Steroidal silicon side-chain analogs as potential antifertility agents

  摘要：

  A number of silicon-substituted analogues of ethynylestradiol that exhibit modified and enhanced biological activities have been synthesized. Particularly noteworthy are a group of [(trialkylsilyl)ethynyl]estradiol analogues that exhibit high antifertility potency and markedly reduced estrogenic activity. The best compounds synthesized are 17 alpha-[(triethylsilyl)ethynyl]estradiol (5) and 17 alpha-[(tert-butyldimethylsilyl)ethynyl]estradiol (33), which show a separation of antifertility from estrogenic activity in the rat. The results of structure-activity studies indicate a good correlation between the observed biological activities and the calculated van der Waals volumes of the three variable silicon substituents.

  DOI：

  10.1021/jm00387a011