6β-Methoxy-3α,5-cyclo-18-nor-5α-pregn-13-en-20α-ol | 143947-68-6

• 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: 6β-Methoxy-3α,5-cyclo-18-nor-5α-pregn-13-en-20α-ol
• CAS: 143947-68-6
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: FNNDWDQOTJFTGH-SGQLRTOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6β-Methoxy-3α,5-cyclo-18-nor-5α-pregn-13-en-20α-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以65%的产率得到6β-Methoxy-3α,5-cyclo-18-nor-5α-pregn-13-en-20-one
  参考文献：
  名称：

  Photoinduced molecular transformations. Part 131. Synthesis of 18-norsteroids, deoxofukujusonorone and the related steroids, based on a selective β-scission of alkoxyl radicals as the key step

  摘要：

  A new transformation of steroids into 18-norsteroids under mild conditions is described. The key step was a regioselective beta-scission of the alkoxyl radicals generated by photolysis of the hypoiodite of 18-hydroxy-18,20-alpha-epoxy steroids, prepared by photolysis of steroidal 20-alpha-ol nitrites followed by deoximation of the resulting 18-hydroxyimino-20-alpha-hydroxy steroid with sodium nitrite and acetic acid. 3-beta-Hydroxypregn-5-en-20-one (pregnenolone) was thus transformed into 3-beta-hydroxy-18-norpregna-5,13-dien-20-one (12-deoxofukujusonorone) in 10 steps.

  DOI：

  10.1039/p19920001837
• 作为产物：
  描述：

  18-Hydroxyimino-6β-methoxy-3α,5-cyclo-5α-pregnan-20β-ol 在 氢氧化钾 、 碘 、 溶剂黄146 、 mercury(II) oxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 31.0h， 生成 6β-Methoxy-3α,5-cyclo-18-nor-5α-pregn-13-en-20α-ol
  参考文献：
  名称：

  Photoinduced molecular transformations. Part 131. Synthesis of 18-norsteroids, deoxofukujusonorone and the related steroids, based on a selective β-scission of alkoxyl radicals as the key step

  摘要：

  A new transformation of steroids into 18-norsteroids under mild conditions is described. The key step was a regioselective beta-scission of the alkoxyl radicals generated by photolysis of the hypoiodite of 18-hydroxy-18,20-alpha-epoxy steroids, prepared by photolysis of steroidal 20-alpha-ol nitrites followed by deoximation of the resulting 18-hydroxyimino-20-alpha-hydroxy steroid with sodium nitrite and acetic acid. 3-beta-Hydroxypregn-5-en-20-one (pregnenolone) was thus transformed into 3-beta-hydroxy-18-norpregna-5,13-dien-20-one (12-deoxofukujusonorone) in 10 steps.

  DOI：

  10.1039/p19920001837