3β-hydroxy-7-norpregn-5-en-20-one | 6695-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3β-hydroxy-7-norpregn-5-en-20-one
• 英文别名: 3β-Hydroxy-B-norpregnen-(5)-on-(20) (B-Norpregnenolon)；3β-Hydroxy-B-nor-pregnen-(5)-on-(20)；20-Oxo-B-nor-pregn-5-en-3β-ol；1-[(3S,3aS,5aS,5bR,8S,10aS,10bS)-8-hydroxy-3a,5b-dimethyl-1,2,3,4,5,5a,6,7,8,9,10a,10b-dodecahydrocyclopenta[a]fluoren-3-yl]ethanone
• CAS: 6695-66-5
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: NTKCNXFTEUDNNA-UZEMSBSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-7-norpregn-5-en-20-one 在 p-chloroperbenzoic acid 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 5,6α-epoxy-20-oxo-7-nor-5α-pregnan-3α-yl formate
  参考文献：
  名称：

  Epalons: 6-Substituted Derivatives of 7-Norepiallopregnanolone

  摘要：

  The target compounds (3 alpha-hydroxy-5,6-epoxy-7-nor-5 alpha-pregnan-20-one, 3 alpha-hydroxy-5,6 beta-epoxy-7-nor-5 beta-pregnan-20-one and 3 alpha-hydroxy-7-nor-5 alpha-pregnane-6,20-dione) were prepared from 5,6 beta-dihydroxy-20-oxo-5 alpha-pregnan-3 beta-yl acetate via the corresponding 5,6-seco acid and 3 beta-acetoxy-20-oxo-7-nor-5 beta,6 alpha-pregnane-6,5-carbolactone-actone. Intermediate 3 beta-hydroxy-7-norpregn-5-en-20-one was converted into the corresponding 5 alpha,6 alpha and 5 beta,6 beta epoxides. The latter was isomerized into 3 beta-hydroxy-7-nor-5 alpha-pregnane-6,20-dione. The configuration of the 3 beta-hydroxy group in these compounds was inverted by Mitsunobu reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00263-5
• 作为产物：
  描述：

  3β-acetoxyl-5β-hydroxyl-6β-formyl-B-norpregnane 在 chromium(VI) oxide 、 氢氧化钾 、 乙酸酐 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 3β-hydroxy-7-norpregn-5-en-20-one
  参考文献：
  名称：

  Tanabe,K. et al., Chemical and pharmaceutical bulletin, 1961, vol. 9, p. 12 - 19

  摘要：

  DOI：

文献信息

• Activity of B-Nor Analogues of Neurosteroids on the GABA_A Receptor in Primary Neuronal Cultures
  作者：Cristina Suñol、Daniel A. García、Jordi Bujons、Zdena Krištofíková、Libor Matyáš、Zoila Babot、Alexander Kasal

  DOI：10.1021/jm060002f

  日期：2006.6.1

  A GABA(A) receptor study of several B-nor analogues of allopregnanolone and pregnanolone has been carried out. B-Norallopregnanolone (i.e., 3 alpha-hydroxy-7-nor-5 alpha-pregnan-20-one) was found comparable to allopregnanolone when measured with labeled TBPS. Analogous results were obtained from their effect on neurons in culture: this time, both 3 alpha-hydroxy-7-nor-5 alpha-pregnan-20-ones (5 and 6) were found to stimulate [H-3] flunitrazepam binding and GABA-induced Cl-36(-) influx. These effects were inhibited by GABA(A) receptor antagonists. Other analogues carrying electronegative substituents (epoxides 9 and 10 and ketone 12) in the B ring were inactive. Similarly, B-normal ketones 17, and 18 and 6-azasteroids 20 and 21 were also inactive. B-Nor analogues 5 and 6 did not induce neurotoxicity at relevant concentrations. A computational analysis of active and inactive neurosteroid analogues allowed the proposal of a 3D pharmacophoric hypothesis of their interaction with the GABA(A) receptor.
• Knof,L., Justus Liebigs Annalen der Chemie, 1962, vol. 657, p. 171 - 178
  作者：Knof,L.

  DOI：——

  日期：——
• Joska,J. et al., Collection of Czechoslovak Chemical Communications, 1961, vol. 26, p. 2050 - 2057
  作者：Joska,J. et al.

  DOI：——

  日期：——
• Sanda,V. et al., Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 3446 - 3451
  作者：Sanda,V. et al.

  DOI：——

  日期：——