17α-ethynyl-7α-methyl-3-oxo-5(10)-estren-17-yl heptanoate | 93176-70-6

• 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-ethynyl-7α-methyl-3-oxo-5(10)-estren-17-yl heptanoate
• 英文别名: [(7R,8R,9S,13S,14S,17R)-17-ethynyl-7,13-dimethyl-3-oxo-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] heptanoate
• CAS: 93176-70-6
• 化学式: C₂₈H₄₀O₃
• 分子量: 424.624
• InChiKey: DEXBNUMRYBIRJT-PHVGWQABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17α-ethynyl-7α-methyl-3-oxo-5(10)-estren-17-yl heptanoate 在 氧气 作用下， 以 四氯化碳 、 正己烷 为溶剂， 反应 21.0h， 以19%的产率得到10β-hydroperoxy-7α-methylnorethindrone 17-heptanoate
  参考文献：
  名称：

  7α-methylnorethindrone enanthate 10β-hydroperoxide: Isolation and characterization

  摘要：

  10 beta-Hydroperoxy-7 alpha-methylnorethindrone 17-heptanoate (II), a product of allylic autoxidation of 7 alpha-methylnorethindrone enanthate (I), has been isolated and characterized. The synthesis of the hydroperoxide (II) from the 3-ethylene ketal of 7 alpha-methylnorethynodrel (III) was achieved. Esterification of alcohol (III), subsequent deketalization, and photochemical oxygenation resulted in the hydroperoxide (II). Reduction of the hydroperoxide (II) to the 10 beta-alcohol (VI) and acetylation of (II) to the 10 beta-acetoxyperoxide (VII) are described. A single subcutaneous injection of the compounds (II), (VI), and (VII) to rats failed to produce long term inhibition of fertility in contrast to the parent compound (I) which is at least five times more effective than norethindrone enanthate as measured by suppression of vaginal cornification and estrous cycles.

  DOI：

  10.1016/0039-128x(83)90138-1
• 作为产物：
  描述：

  3-ethylenedioxy-17α-ethynyl-7α-methyl-5(10)-estren-17-yl heptanoate 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.3h， 以72%的产率得到17α-ethynyl-7α-methyl-3-oxo-5(10)-estren-17-yl heptanoate
  参考文献：
  名称：

  7α-methylnorethindrone enanthate 10β-hydroperoxide: Isolation and characterization

  摘要：

  10 beta-Hydroperoxy-7 alpha-methylnorethindrone 17-heptanoate (II), a product of allylic autoxidation of 7 alpha-methylnorethindrone enanthate (I), has been isolated and characterized. The synthesis of the hydroperoxide (II) from the 3-ethylene ketal of 7 alpha-methylnorethynodrel (III) was achieved. Esterification of alcohol (III), subsequent deketalization, and photochemical oxygenation resulted in the hydroperoxide (II). Reduction of the hydroperoxide (II) to the 10 beta-alcohol (VI) and acetylation of (II) to the 10 beta-acetoxyperoxide (VII) are described. A single subcutaneous injection of the compounds (II), (VI), and (VII) to rats failed to produce long term inhibition of fertility in contrast to the parent compound (I) which is at least five times more effective than norethindrone enanthate as measured by suppression of vaginal cornification and estrous cycles.

  DOI：

  10.1016/0039-128x(83)90138-1