10β-Fluoro-3-oxo-1,4-estradiene-16α,17β-diol 16,17-diacetate | 138054-65-6

• 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: 10β-Fluoro-3-oxo-1,4-estradiene-16α,17β-diol 16,17-diacetate
• 英文别名: [(8S,9S,10S,13S,14S,16R,17R)-17-acetyloxy-10-fluoro-13-methyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl] acetate
• CAS: 138054-65-6
• 化学式: C₂₂H₂₇FO₅
• 分子量: 390.452
• InChiKey: LLLHUBXXXZKPEH-ZOSSLFJCSA-N

物化性质

• 沸点：
  482.6±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  69.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  雌三醇 16,17-二乙酸酯 在 N-fluorobis<(trifluoromethyl)sulfonyl>imide 作用下， 以 溶剂黄146 为溶剂， 以84%的产率得到10β-Fluoro-3-oxo-1,4-estradiene-16α,17β-diol 16,17-diacetate
  参考文献：
  名称：

  Para fluorination by N-fluorobis[(trifluoromethyl)sulfonyl]imide: synthesis of 10.beta.-fluoro-3-oxo-1,4-estradiene steroids

  摘要：

  When 1,3,5(10)-estratrien-3-ols are treated with N-fluorobis[(trifluoromethyl)sulfonyl]imide in chloroform solution the ortho and para fluorination products are formed. In contrast, when acetic acid is used as a solvent, fluorination in the para position occurs selectively and 10-beta-fluoro-3-oxo-1,4-estradiene derivatives are formed in high yields.

  DOI：

  10.1021/jo00031a038

文献信息

• Para fluorination by N-fluorobis[(trifluoromethyl)sulfonyl]imide: synthesis of 10.beta.-fluoro-3-oxo-1,4-estradiene steroids
  作者：William T. Pennington、Giuseppe Resnati、Darryl D. DesMarteau

  DOI：10.1021/jo00031a038

  日期：1992.2

  When 1,3,5(10)-estratrien-3-ols are treated with N-fluorobis[(trifluoromethyl)sulfonyl]imide in chloroform solution the ortho and para fluorination products are formed. In contrast, when acetic acid is used as a solvent, fluorination in the para position occurs selectively and 10-beta-fluoro-3-oxo-1,4-estradiene derivatives are formed in high yields.