17β-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one trifluoroacetate

• 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: 17β-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one trifluoroacetate
• 英文别名: [(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] 2,2,2-trifluoroacetate
• 化学式: C₂₂H₂₅F₃O₃
• 分子量: 394.434
• InChiKey: PSZLMCZQMMZTPW-JAYAMIOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one trifluoroacetate 在 甲酸 作用下， 反应 0.67h， 以47%的产率得到17,17a-dimethyl-D-homogona-4,13,15,17(17a)-tetraen-3-one
  参考文献：
  名称：

  Steroids 49. Investigations on the dehydration of 17α-ethynl-17β- hydroxysteroids

  摘要：

  The acidic dehydration of 17alpha-ethynyl-17beta-hydroxysteroids (1-3) was investigated. On reaction with thionyl chloride, phosphorus oxychloride, and formic acid, the desired dehydration was accompanied by chlorination, Wagner-Meerwein rearrangement, and D-homoaromatic rearrangement. The structure of the product from the transformation of 17beta-hydroxypregn-20-yne derivative (3) on reaction with formic acid was misjudged. It was regarded as a pregn-16-en-20-yne (10) instead of the actually rearranged D-homoaromatic compound (11). As a consequence, physical data corresponding to this latter structure have been cited in the literature as those of pregn-16-en-20-yne derivative (10). This confusion prompted us to prepare compounds of both types (4, 9, 10, and 11), the characterization of which is here described.

  DOI：

  10.1016/0039-128x(93)90022-f
• 作为产物：
  描述：

  炔诺酮 、 三氟乙酸酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以95%的产率得到17β-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one trifluoroacetate
  参考文献：
  名称：

  Steroids 49. Investigations on the dehydration of 17α-ethynl-17β- hydroxysteroids

  摘要：

  The acidic dehydration of 17alpha-ethynyl-17beta-hydroxysteroids (1-3) was investigated. On reaction with thionyl chloride, phosphorus oxychloride, and formic acid, the desired dehydration was accompanied by chlorination, Wagner-Meerwein rearrangement, and D-homoaromatic rearrangement. The structure of the product from the transformation of 17beta-hydroxypregn-20-yne derivative (3) on reaction with formic acid was misjudged. It was regarded as a pregn-16-en-20-yne (10) instead of the actually rearranged D-homoaromatic compound (11). As a consequence, physical data corresponding to this latter structure have been cited in the literature as those of pregn-16-en-20-yne derivative (10). This confusion prompted us to prepare compounds of both types (4, 9, 10, and 11), the characterization of which is here described.

  DOI：

  10.1016/0039-128x(93)90022-f

文献信息

• Verfahren zur Herstellung von Pregn-4-en-3,20-dionderivaten sowie 17-alpha-Äthinyl-17-beta-trifluoracetoxygon-4-en-3-onderivate und die letzteren enthaltende Arzneimittel
  申请人：RICHTER GEDEON VEGYESZETI GYAR R.T.

  公开号：EP0063368B1

  公开（公告）日：1984-07-25
• US4368160A
  申请人：——

  公开号：US4368160A

  公开（公告）日：1983-01-11
• US4482494A
  申请人：——

  公开号：US4482494A

  公开（公告）日：1984-11-13