18-Hydroxyimino-6β-methoxy-3α,5-cyclo-5α-pregnan-20β-ol | 143947-59-5

• 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: 18-Hydroxyimino-6β-methoxy-3α,5-cyclo-5α-pregnan-20β-ol
• 英文别名: 18-Hydroxyimino-6β-methoxy-3α,5-cyclo-5α-pregnan-20α-ol
• CAS: 143947-59-5；143947-61-9
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: QDMRHKPCVZDZKZ-WUBORRSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  62.05
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  18-Hydroxyimino-6β-methoxy-3α,5-cyclo-5α-pregnan-20β-ol 在 氢氧化钾 、 碘 、 溶剂黄146 、 pyridinium chlorochromate 、 mercury(II) oxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 48.0h， 生成 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：

  以 甲醇 、 苯 为溶剂， 反应 1.0h， 以63%的产率得到18-Hydroxyimino-6β-methoxy-3α,5-cyclo-5α-pregnan-20β-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