20-isocyanopregna-4,16,20-trien-3-one | 149398-83-4

• 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: 20-isocyanopregna-4,16,20-trien-3-one
• CAS: 149398-83-4
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: HCNDKFLSNAIYAV-JFZIVLOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  21.43
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  20-isocyanopregna-4,16,20-trien-3-one 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Introduction of 20-keto side chains in 17-oxosteroids: Wittig-Horner-Emmons reactions of (E)-17-[(diethylphosphino)isocyanomethylene]-3-methoxyandrosta-3,5-diene

  摘要：

  The synthesis is described of a series of polyfunctional unsaturated DELTA16,20-20-isocyanosteroids 5a-f by the Wittig-Horner-Emmons reaction of (E)-17-[(diethylphosphono)isocyanomethylene] steroid 4 with several aldehydes and with acetone. Hydrolysis of the isocyanosteroids 5a-f with dilute sulfuric acid gave DELTA16-20-ketosteroids 6a-f in high yield. Hydrolysis of 5a was also possible under neutral conditions, via the intermediate DELTA16-20-20-isocyanatosteroid 7a, leading to A-ring protected 16-dehydroprogesterone 8a. The Wittig-Horner-Emmons reaction, together with the described hydrolyses, provides a new method for the introduction of steroid side chains. The method is particularly suited for side chains of different size, structure, and functionality.

  DOI：

  10.1021/jo00066a021
• 作为产物：
  描述：

  20-Isocyano-3-methoxypregna-3,5,16,20-tetraene 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到20-isocyanopregna-4,16,20-trien-3-one
  参考文献：
  名称：

  Introduction of 20-keto side chains in 17-oxosteroids: Wittig-Horner-Emmons reactions of (E)-17-[(diethylphosphino)isocyanomethylene]-3-methoxyandrosta-3,5-diene

  摘要：

  The synthesis is described of a series of polyfunctional unsaturated DELTA16,20-20-isocyanosteroids 5a-f by the Wittig-Horner-Emmons reaction of (E)-17-[(diethylphosphono)isocyanomethylene] steroid 4 with several aldehydes and with acetone. Hydrolysis of the isocyanosteroids 5a-f with dilute sulfuric acid gave DELTA16-20-ketosteroids 6a-f in high yield. Hydrolysis of 5a was also possible under neutral conditions, via the intermediate DELTA16-20-20-isocyanatosteroid 7a, leading to A-ring protected 16-dehydroprogesterone 8a. The Wittig-Horner-Emmons reaction, together with the described hydrolyses, provides a new method for the introduction of steroid side chains. The method is particularly suited for side chains of different size, structure, and functionality.

  DOI：

  10.1021/jo00066a021