16α,17α-epoxy-3β-formyloxypregn-5-en-20-one | 4420-27-3

• 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: 16α,17α-epoxy-3β-formyloxypregn-5-en-20-one
• 英文别名: 3β-Formyloxy-16α,17α-epoxy-pregnen-5-on-20；3β-Formyloxy-16α,17α-epoxy-20-oxo-Δ⁵-pregnen；16α,17-epoxy-3β-formyloxy-pregn-5-en-20-one；16α,17-Epoxy-3β-formyloxy-pregn-5-en-20-on；[(1R,2S,4R,6S,7S,10S,11R,14S)-6-acetyl-7,11-dimethyl-5-oxapentacyclo[8.8.0.02,7.04,6.011,16]octadec-16-en-14-yl] formate
• CAS: 4420-27-3
• 化学式: C₂₂H₃₀O₄
• 分子量: 358.478
• InChiKey: OWCAJDYRRYHSHE-LNFFIUOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16α,17α-epoxy-3β-formyloxypregn-5-en-20-one 生成 5-孕烯-3-beta,16-alpha-二醇-20-酮
  参考文献：
  名称：

  Synthesis of Polyhydroxy-steroids. II. Syntheses of Isomeric 5α-Pregnane-3, 5, 6, 16, 20-pentols and Related Compounds.

  摘要：

  考虑到5α-孕烯-3β, 5, 6β, 16β, 20α-五醇（POL）在动物实验中表现出与SEF相似的有趣的排钠活性，合成了一些在C-3、C-5、C-6、C-16和C-20位上具有羟基或羰基的多氧化孕烷化合物。同时还描述了3β, 5, 6β, 16α-四羟基-5α-孕烯-20-酮的合成，这是一种POL和SEF的杂合化合物。

  DOI：

  10.1248/cpb.11.95
• 作为产物：
  描述：

  N-(chloromethylidene) N-methylmethanaminium 、 16,17-环氧孕烯醇酮 在 N,N-二甲基甲酰胺 作用下， 生成 16α,17α-epoxy-3β-formyloxypregn-5-en-20-one
  参考文献：
  名称：

  Morita et al., Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 896

  摘要：

  DOI：

文献信息

• Highly efficient Lewis acid catalyzed, one step conversions of 16α,17α-epoxy-3β-hydroxypregn-5-en-20-one to d-homosteroid and Δ13-steroids
  作者：Navdeep K Girdhar、M.P.S Ishar、Rajiv Kumar、Rajinder Singh、Gurmit Singh

  DOI：10.1016/s0040-4020(01)00673-1

  日期：2001.8

  Conversion of 16 alpha ,17 alpha -epoxy-3 beta -hydroxypregn-5-en-20-one (1a) to 16 beta -chloro-3 beta ,17 alpha -dihydroxy-17 beta -methyl-17a-homoandrost-5-en-17a-one (3) in very high yields (95%), in one step by treatment with 3 equiv. of anhyd. AlCl3, has been achieved; use of two equiv. of AlCl3 affords mixture Of D-homosteroid 3 (70%) and chlorohydrin 4 (27%). On the other hand, treatment of la with excess of acetic anhydride and anhydrous ZnCl2 at room temperature leads to reversal of the direction of epoxide ring opening with concomitant methyl migration, leading to 3 beta ,16 alpha -diacetoxy-17-methyl-17 alpha -pregna-5,13-diene-20-one (6) in high yield (92%). The conversions are a remarkable improvement over related routes in terms of both yield and selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.