11β-hydroxy-9β-estrone | 78854-36-1

• 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: 11β-hydroxy-9β-estrone
• 英文别名: (8S,9R,11S,13S,14S)-3,11-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 78854-36-1
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: IGSYRIQHXYIOHU-OIDVLUPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  11-Keto-9β-estrone 17-ethyleneketal 在 盐酸 、 sodium 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 0.58h， 生成 11β-hydroxy-9β-estrone
  参考文献：
  名称：

  Structure-activity relationships of four 11-hydroxyestrones isomeric at the C-9 and C-11 positions

  摘要：

  The synthesis of 11 alpha-hydroxyestrone, 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxy-9 beta-estrone are presented. The reduction of 11-keto-9 beta-estrone 17-ethyleneketal by sodium in ethanol or sodium borohydride resulted in 11-hydroxy-9 beta-estrones. The 11-hydroxyl group configurations were opposite to expectations: sodium in boiling ethanol afforded the axial 11 beta-hydroxy-9 beta-estrone, while sodium borohydride in boiling tetrahydrofuran gave the equatorial 11 alpha-hydroxy-9 beta-estrone. In immature rat uterotropic bioassays using subcutaneous injections, 11 alpha-hydroxyestrone was 2 times as active as 11 alpha-hydroxy-9 beta-estrone, and 11 beta-hydroxyestrone was 10 times as active as 11 beta-hydroxy-9 beta-estrone.

  DOI：

  10.1016/s0039-128x(81)90234-8