5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one | 13485-13-7

• 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: 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one
• 英文别名: 16-dehydropregnenolone-5α,6α-epoxide；5α,6α-epoxy-3β-hydroxy-pregn-16-en-20-one；1-[(1S,2R,5S,7R,9S,11S,12S,16S)-5-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-14-en-15-yl]ethanone
• CAS: 13485-13-7
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: FJOFXGFQXDZWJF-XQYCTUDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one 在 Trichoderma Viride 作用下， 以 丙酮 为溶剂， 反应 96.0h， 以291 mg的产率得到3β,5α,6β-trihydroxypregn-16-en-20-one
  参考文献：
  名称：

  Microbial transformation of 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one by Trichoderma viride

  摘要：

  Fermentation of 5 alpha,6 alpha-epoxy-3 beta-hydroxy-16-pregnen-20-one (4) with Trichoderma viride under aerobic condition yielded 3 beta,5 alpha,6 beta-trihydroxy-16-pregnen-20-one (5) and 3 beta,5 alpha,6 alpha, 15p-tetrahydroxy-16-pregnen-20-one (6). Each microbial metabolite was characterized by spectroscopic methods. Compounds 6 and 3 beta,5 alpha,15 beta-trihydroxy-16-pregnen-6,20-dione (7) are reported for the first time. (c) 2007 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2006.12.009
• 作为产物：
  描述：

  3β-acetoxy-5,6-epoxy-16-pregnen-20-one 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以76%的产率得到5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one
  参考文献：
  名称：

  Microbial transformation of 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one by Trichoderma viride

  摘要：

  Fermentation of 5 alpha,6 alpha-epoxy-3 beta-hydroxy-16-pregnen-20-one (4) with Trichoderma viride under aerobic condition yielded 3 beta,5 alpha,6 beta-trihydroxy-16-pregnen-20-one (5) and 3 beta,5 alpha,6 alpha, 15p-tetrahydroxy-16-pregnen-20-one (6). Each microbial metabolite was characterized by spectroscopic methods. Compounds 6 and 3 beta,5 alpha,15 beta-trihydroxy-16-pregnen-6,20-dione (7) are reported for the first time. (c) 2007 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2006.12.009

文献信息

• Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate
  作者：João F.S. Carvalho、M. Manuel Cruz Silva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2009.01.100

  日期：2009.4

  Fast generation of epoxides from the corresponding homoallylic and allylic steroidal olefins was developed by using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) as oxidant suspended in acetonitrile (CH3CN) at reflux temperature. The protocol involves the use of a safe readily available oxidant along with an easy work-up, which renders the process very efficient. Selective 4,5- and 5,6-epoxidations

  通过在回流温度下使用悬浮在乙腈（CH 3 CN）中的双（双过氧邻苯二甲酸酯）六水合镁（MMPP）作为氧化剂，可以从相应的均烯丙基和烯丙基甾体烯烃快速生成环氧化物。该方案涉及使用安全易得的氧化剂以及易于后处理的方法，这使该过程非常有效。据报道类固醇的选择性4，5-和5，6-环氧化。其中，Δ的高立体选择性环氧化5 -B去甲胆甾烷达到了。而且，该方法对5，6-位是化学选择性的，可用于环A烯酮的环氧化。
• Chemoselective epoxidation of cholesterol derivatives on a surface-designed molecularly imprinted Ru–porphyrin catalyst
  作者：Satoshi Muratsugu、Hiroshi Baba、Tatsuya Tanimoto、Kana Sawaguchi、Satoru Ikemoto、Masahiro Tasaki、Yosuke Terao、Mizuki Tada

  DOI：10.1039/c8cc00896e

  日期：——

  High chemoselectivity for the C₅C₆epoxidation of cholesterol derivatives without protecting other oxidizable functional groups was achieved on a newly designed molecularly imprinted Ru–porphyrin catalyst using a SiO₂-support.

  胆固醇衍生物的C5-C6环氧化具有高度的化学选择性，而不需要保护其他可氧化的官能团，在新设计的分子印迹Ru-卟啉催化剂上实现，该催化剂使用SiO2支撑。
• Microbial transformation of 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one by Trichoderma viride
  作者：Hong-Min Liu、Wenzhong Ge、Heping Li、Jian Wu

  DOI：10.1016/j.steroids.2006.12.009

  日期：2007.6

  Fermentation of 5 alpha,6 alpha-epoxy-3 beta-hydroxy-16-pregnen-20-one (4) with Trichoderma viride under aerobic condition yielded 3 beta,5 alpha,6 beta-trihydroxy-16-pregnen-20-one (5) and 3 beta,5 alpha,6 alpha, 15p-tetrahydroxy-16-pregnen-20-one (6). Each microbial metabolite was characterized by spectroscopic methods. Compounds 6 and 3 beta,5 alpha,15 beta-trihydroxy-16-pregnen-6,20-dione (7) are reported for the first time. (c) 2007 Published by Elsevier Inc.