6β-methoxy-3α,5α:18,20-dicyclopregnan-20β-ol | 143882-41-1

• 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: 6β-methoxy-3α,5α:18,20-dicyclopregnan-20β-ol
• 英文别名: (1S,2S,5S,6R,8R,11S,12R,15R,17R,18R)-18-methoxy-6,12-dimethylhexacyclo[9.8.0.02,8.05,8.012,17.015,17]nonadecan-6-ol
• CAS: 143882-41-1
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: VLMZYVPJOITYKL-LUOIICGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6β-methoxy-3α,5α:18,20-dicyclopregnan-20β-ol 在 吡啶 、 亚硝酰氯 作用下， 以 甲醇 、 苯 为溶剂， 反应 1.08h， 生成 (E)-6β-methoxy-3α,5-cyclo-18a,18b-dihomo-5α-androstane-17,18a-dione 17-oxime
  参考文献：
  名称：

  Photoinduced molecular transformations. Part 132. A two-step intramolecular transposition of the 17β-acetyl group of pregnan-20-one to C-18 through the formation of cyclobutanols by the reaction of the excited carbonyl, followed by a selective β-scission of alkoxyl radicals generated from them

  摘要：

  New two-step transformations of a pregnan-20-one into 18-functionalized androstanes and 18a,18b-dihomoandrostanes are described; a type-II reaction of an excited pregnan-20-one protected in the A,B-ring gave the corresponding 20-hydroxy-18,20-cyclopregnane. Selective beta-scission of the cyclobutanoxyl radicals generated by irradiation of the nitrite or the hypoiodite gave a 5:4 ratio of the corresponding 18a,18b-dihomo-5-alpha-androstan-18a-one and 18-iodoandrostan-17-beta-yl acetate in 89% yield or 18a,18b-dihomo-5-alpha-androstane-17,18a-dione 17-oxime in 83% yield. The transformation involves a novel two-step intramolecular transposition of the 17-beta-acetyl group to C-18, and an oxygen insertion to the C-17-C-20 bond of pregnan-20-one.Several chemoselective transformations of the functional groups of the 18-iodoandrostan-17-one and 18a,18b-dihomo-5-alpha-pregnan-18a-one, including the synthesis of 3-beta-hydroxy-18a,18b-dihomoandrost-5-ene-17,18a-dione, are reported.

  DOI：

  10.1039/p19920001843
• 作为产物：
  描述：

  (20S)-3α,5-cyclo-20-formyl-6β-methoxy-5α-pregnane 以 乙醇 为溶剂， 反应 3.0h， 以39%的产率得到6β-methoxy-3α,5α:18,20-dicyclopregnan-20β-ol
  参考文献：
  名称：

  Photoinduced molecular transformations. Part 132. A two-step intramolecular transposition of the 17β-acetyl group of pregnan-20-one to C-18 through the formation of cyclobutanols by the reaction of the excited carbonyl, followed by a selective β-scission of alkoxyl radicals generated from them

  摘要：

  New two-step transformations of a pregnan-20-one into 18-functionalized androstanes and 18a,18b-dihomoandrostanes are described; a type-II reaction of an excited pregnan-20-one protected in the A,B-ring gave the corresponding 20-hydroxy-18,20-cyclopregnane. Selective beta-scission of the cyclobutanoxyl radicals generated by irradiation of the nitrite or the hypoiodite gave a 5:4 ratio of the corresponding 18a,18b-dihomo-5-alpha-androstan-18a-one and 18-iodoandrostan-17-beta-yl acetate in 89% yield or 18a,18b-dihomo-5-alpha-androstane-17,18a-dione 17-oxime in 83% yield. The transformation involves a novel two-step intramolecular transposition of the 17-beta-acetyl group to C-18, and an oxygen insertion to the C-17-C-20 bond of pregnan-20-one.Several chemoselective transformations of the functional groups of the 18-iodoandrostan-17-one and 18a,18b-dihomo-5-alpha-pregnan-18a-one, including the synthesis of 3-beta-hydroxy-18a,18b-dihomoandrost-5-ene-17,18a-dione, are reported.

  DOI：

  10.1039/p19920001843