18-iodo-3β-methoxyandrost-5-en-17β-ol | 143882-45-5

• 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-iodo-3β-methoxyandrost-5-en-17β-ol
• 英文别名: (3S,8R,9S,10R,13R,14S,17S)-13-(iodomethyl)-3-methoxy-10-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 143882-45-5
• 化学式: C₂₀H₃₁IO₂
• 分子量: 430.369
• InChiKey: YFWPKPVYJUUAGX-IJMQKCTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• 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：

  18-iodo-3β-methoxyandrost-5-en-17β-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以52%的产率得到18-iodo-3β-methoxyandrost-5-en-17-one
  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：

  18-iodo-6β-methoxy-3α,5α-cyclo-5α-androstan-17-yl acetate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 5.5h， 以56%的产率得到18-iodo-3β-methoxyandrost-5-en-17β-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

文献信息

• 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
  作者：Hiroshi Suginome、Yutaka Nakayama

  DOI：10.1039/p19920001843

  日期：——

  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.