3-methoxy-D-homoestra-1,3,5(10)-triene-17β,17αβ-diol | 21887-13-8

• 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: 3-methoxy-D-homoestra-1,3,5(10)-triene-17β,17αβ-diol
• 英文别名: (1R,2S,4aS,4bR,10bS,12aS)-8-methoxy-12a-methyl-2,3,4,4a,4b,5,6,10b,11,12-decahydro-1H-chrysene-1,2-diol
• CAS: 21887-13-8
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: XFQKACAXJUWIDT-MILMJNAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-D-homoestra-1,3,5(10)-triene-17β,17αβ-diol 在 titanium(III) chloride 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 36.0h， 以92%的产率得到3-methoxy-D-homoestra-1,3,5(10),17-tetraene
  参考文献：
  名称：

  New low-valent titanium reagents for dicarbonyl coupling and their use in a general method of annulation

  摘要：

  New low-valent titanium reagents have been prepared by reducing TiCl3 (1 mol) with C8K (2 mol) or by reducing TiCl4 (1 mol) with Na-naphthalene (2.75 mol). Ketones carrying a chain that incorporates a suitably placed oxo function (aldehyde or ketone) undergo intramolecular dicarbonyl coupling to produce a bicyclic compound when treated with an excess (16-17 mol of titanium halide per mol of dicarbonyl compound) of one of these reagents. The procedure works well even for highly oxygenated substrates and constitutes a general method of annulation. Other reducing agents besides C8K or Na-naphthalene are suitable, and a brief examination of Na(Hg) and Na-K alloy was made. The C8K/TiCl3 system was also used to convert a cis-1,2-diol into the corresponding olefin.

  DOI：

  10.1021/jo00022a042