21-hydroxypregna-1,4,17(20)trien-3-one | 119364-22-6

• 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: 21-hydroxypregna-1,4,17(20)trien-3-one
• 英文别名: Pregna-1,4,17(20)-triene-21-ol-3-one；(8S,9S,10R,13S,14S)-17-(2-hydroxyethylidene)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
• CAS: 119364-22-6
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: TYTKGJVQFMAZBJ-FCMAGTKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  21-hydroxypregna-1,4,17(20)trien-3-one 生成 3a-methyl-7-[2-(5-hydroxy-2-methylphenyl)-ethyl]-3-(2-hydroxyethylidene)-octahydro-5H-inden-5-one
  参考文献：
  名称：

  Amino-9,10-secosteroids useful for treating head injury, spinal cord

  摘要：

  本发明的氨基-9,10-次甾体类固醇包含一个氨基团附加在C.sub.17-侧链的末端碳原子上，并可用作治疗多种病症的药物，包括脊柱创伤、轻度和/或中度至重度头部创伤等。

  公开号：

  US04996318A1

文献信息

• Process for the partial reduction of C21-steroid carboxylic acids and
  申请人：Henkel Kommanditgesellschaft auf Aktien (Henkel KGaA)

  公开号：US04370271A1

  公开（公告）日：1983-01-25

  A process for the partial reduction of C21-steroid carboxylic acids and their esters to C21-steroid alcohols and new C21-steroid alcohols .DELTA.4,17(20)-C21-steroid carboxylic acids optionally containing further double bonds in the 1- and/or 9(11)-position and their esters corresponding to general formula I below ##STR1## in which R represents hydrogen or a hydrocarbon radical and A represents hydrogen, hydroxyl or, together with the C-atom substituted by A, a carbonyl group and in which, finally, the substituent A may even be replaced by an additional olefinic double bond in the 9(11)-position, are reacted with diisobutyl aluminium hydride without the A-ring in the steroid skeleton being blocked in such quantities that all the oxygen-containing functional groups are reduced to the hydroxyl group. The aluminium-containing intermediate reaction product is then subjected to the selective Oppenauer oxidation to form the 3-keto compound. The 3-oxo-C21-steroid alcohols may be obtained in high yields in this way. The process is suitable for the preparation of pharmacologically active steroid compounds having the 17,21-diol-20-one configuration. It enables the new compuonds, pregna-1,4,17(20)-triene-3-one-21-ol and pregna-1,4,9(11),17(20)-tetraene-3-one-21-ol and their 21-acetoxy compounds, to be obtained.

  一种部分还原C21类固醇羧酸和其酯为C21类固醇醇和新的C21类固醇醇.DELTA.4,17（20）-C21类固醇羧酸，可选地在1-和/或9（11）-位置含有进一步的双键，以及它们的酯，对二异丁基铝氢化物进行反应，而不阻塞类固醇骨架中的A环，使所有含氧官能团还原为羟基。然后将含铝的中间反应产物进行选择性Oppenauer氧化，形成3-酮化合物。通过这种方式可以高产率地获得3-氧代C21类固醇醇。该过程适用于制备具有17,21-二醇-20-酮构型的药理活性类固醇化合物。它使得可以获得新的化合物，孕酮-1,4,17（20）-三烯-3-酮-21-醇和孕酮-1,4,9（11），17（20）-四烯-3-酮-21-醇及其21-乙酰氧化合物。