3β-hydroxy-5α-pregn-16-ene-11,20-dione | 600-60-2

• 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: 3β-hydroxy-5α-pregn-16-ene-11,20-dione
• 英文别名: 3β-Hydroxy-5α-pregn-16-en-11,20-dion；3beta-Hydroxy-5alpha-pregn-16-ene-11,20-dione；(3S,5S,8S,9S,10S,13S,14S)-17-acetyl-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15-dodecahydrocyclopenta[a]phenanthren-11-one
• CAS: 600-60-2
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: BAIJWZQSAKPKNT-ASOOTTPISA-N

物化性质

• 沸点：
  483.2±45.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)
• 熔点：
  188-190 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-5α-pregn-16-ene-11,20-dione 在 对甲苯磺酸 作用下， 以 乙二醇 、 苯 为溶剂， 生成 20,20-ethanediyldioxy-3β-hydroxy-5α-pregn-16-en-11-one
  参考文献：
  名称：

  Chemical compounds

  摘要：

  孕烷和雄烷是描述具有3.alpha.-羟基、5.alpha.-氢原子或4,5-或5,6-双键、17.alpha.-氢原子和11.beta.-氨基酯基团的化合物。其他可选的取代基或双键可能存在。这些化合物具有麻醉活性。

  公开号：

  US04192871A1
• 作为产物：
  描述：

  3b-乙酰氧基-5a-孕甾-16-烯-11,20-二酮 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 生成 3β-hydroxy-5α-pregn-16-ene-11,20-dione
  参考文献：
  名称：

  Anaesthetic steroids of the androstance and pregnane series

  摘要：

  具有2.alpha.-氢或卤素或烷基；3.alpha.-羟基或酰氧基，3.beta.-氢或烷基；11.beta.-氢或羟基或环氧基，也与9位点连接；11.alpha.-氢或烷基或烯丙基；或11-酮基；16氢或卤素或甲基或二甲基基团；20-酮基或乙二氧基基团；和20-甲基或烷氧基团的雄甾烷和孕甾烷系列类固醇。这些化合物在1(2)、8(9)或9(11)位点可能不饱和。这些化合物具有麻醉特性。

  公开号：

  US03953429A1

文献信息

• Anaesthetic composition containing a steroid of the 5.alpha.-pregnane
  申请人：Glaxo Laboratories Limited

  公开号：US03952031A1

  公开（公告）日：1976-04-20

  This invention relates to steroids of the pregnane and 19-norpregnane series having anaesthetic properties and compositions containing them. More particularly the present invention relates to such steroids having a variety of substituents in the 2.beta.-position, a 3.alpha.-hydroxy group and a 5.alpha.-hydrogen atom and esters and 20-ketals thereof. At the 11-position of such steroids is preferably either two hydrogen atoms or an oxo group. The compounds according to the invention may conveniently be prepared by reaction of an appropriate 2.alpha.,3.alpha.-epoxy-pregnane or 19-norpregnane with a reagent which introduces the desired 2.beta.-substituent and various modifications of the compound produced are described to produce compounds within the scope of the invention. The present invention provides compositions containing certain steroids of the pregnane and 19-norpregnane series and such compositions generally may be administered intravenously to induce anaesthesia, the invention providing methods of inducing anaesthesia.

  这项发明涉及具有麻醉特性的孕烷和19-去甲孕烷系列类固醇以及含有它们的组合物。更具体地，本发明涉及具有2.beta.-位上各种取代基、3.alpha.-羟基和5.alpha.-氢原子以及其酯和20-酮缩醛的类固醇。在这种类固醇的11位上最好是两个氢原子或一个酮基团。根据本发明的化合物可以通过将适当的2.alpha.,3.alpha.-环氧孕烷或19-去甲孕烷与引入所需的2.beta.-取代基的试剂反应来方便地制备，并描述了所产生化合物的各种修饰以制备属于本发明范围内的化合物。本发明提供了含有孕烷和19-去甲孕烷系列某些类固醇的组合物，这些组合物通常可通过静脉注射来诱导麻醉，本发明提供了诱导麻醉的方法。
• Action of Some Steroids on the Central Nervous System of the Mouse. I. Synthetic Methods
  作者：J. D. Cocker、J. Elks、P. J. May、F. A. Nice、G. H. Phillipps、W. F. Wall

  DOI：10.1021/jm00328a003

  日期：1965.7
• 3beta-oxy-delta16-allopregnenedione-11, 20 and process
  申请人：MERCK &

  公开号：US02779774A1

  公开（公告）日：1957-01-29
• 3(beta)-acetoxy-16(delta-acetoxyisocaprooxy)-allopregnanedione-11, 20
  申请人：MERCK &

  公开号：US02716125A1

  公开（公告）日：1955-08-23
• Neurosteroid analogues. 15. A comparative study of the anesthetic and GABAergic actions of alphaxalone, Δ16-alphaxalone and their corresponding 17-carbonitrile analogues
  作者：Achintya K. Bandyopadhyaya、Brad D. Manion、Ann Benz、Amanda Taylor、Nigam P. Rath、Alex S. Evers、Charles F. Zorumski、Steven Mennerick、Douglas F. Covey

  DOI：10.1016/j.bmcl.2010.09.008

  日期：2010.11

  Alphaxalone, a neuroactive steroid containing a 17 beta-acetyl group, has potent anesthetic activity in humans. This pharmacological activity is attributed to this steroid's enhancement of gamma-amino butyric acid-mediated chloride currents at gamma-amino butyric acid type A receptors. The conversion of alphaxalone into Delta(16)-alphaxalone produces an analogue that lacks anesthetic activity in humans and that has greatly diminished receptor actions. By contrast, the corresponding 17 beta-carbonitrile analogue of alphaxalone and the Delta(16)-17-carbonitrile analogue both have potent anesthetic and receptor actions. The differential effect of the Delta(16)-double bond on the actions of alphaxalone and the 17 beta-carbonitrile analogue is accounted for by a differential effect on the orientation of the 17-acetyl and 17-carbonitrile substituents. (C) 2010 Elsevier Ltd. All rights reserved.