17α-<(triethylsilyl)ethynyl>estra-3,17β-diol | 50866-95-0

• 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: 17α-<(triethylsilyl)ethynyl>estra-3,17β-diol
• 英文别名: 21-(triethylsilyl)-19-norpregna-1,3,5(10)-trien-20-yne-3,17β-diol；17α-[(triethylsilyl)ethynyl]estra-3,17β-diol；(8R,9S,13S,14S,17S)-13-methyl-17-(2-triethylsilylethynyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 50866-95-0
• 化学式: C₂₆H₃₈O₂Si
• 分子量: 410.672
• InChiKey: OXGNVYXRERJVBT-PUHDZGQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17α-<(triethylsilyl)ethynyl>estra-3,17β-diol 在 Pd-BaSO₄ 氢气 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以25%的产率得到17α-estra-3,17β-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
• 作为产物：
  描述：

  炔雌醇 在 盐酸 、 乙基溴化镁 作用下， 以 甲醇 、 水 为溶剂， 反应 39.0h， 生成 17α-<(triethylsilyl)ethynyl>estra-3,17β-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

文献信息

• Steroidal silicon side-chain analogs as potential antifertility agents
  作者：Richard H. Peters、David F. Crowe、Masato Tanabe、Mitchell A. Avery、Wesley K. M. Chong

  DOI：10.1021/jm00387a011

  日期：1987.4

  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.