5α,6α-epoxy-7-nor-5α-cholestan-3β-yl acetate | 40005-35-4

• 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-7-nor-5α-cholestan-3β-yl acetate
• 英文别名: acetic acid-(5,6α-epoxy-B-nor-5α-cholestan-3β-yl ester)；Essigsaeure-(5,6α-epoxy-B-nor-5α-cholestan-3β-ylester)；5α,6α-Epoxy-B-norcholestanol-(3β)-acetat；3β-Acetoxy-5α,6α-epoxy-B-norcholestan；3β-Acetoxy-5α,6α-oxido-B-norcholestan；5alpha,6alpha-Epoxy-7-norcholestan-3beta-yl acetate；[(1S,2S,4R,6S,9R,10S,13R,14R,17S)-9,13-dimethyl-14-[(2R)-6-methylheptan-2-yl]-3-oxapentacyclo[8.7.0.02,4.04,9.013,17]heptadecan-6-yl] acetate
• CAS: 40005-35-4
• 化学式: C₂₈H₄₆O₃
• 分子量: 430.671
• InChiKey: LBQTXYZZLUJRME-SMQGDZKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α,6α-epoxy-7-nor-5α-cholestan-3β-yl acetate 在 辛醇 、 Candida cylindracea lipase AY 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以96%的产率得到5α,6α-epoxy-7-norcholestan-3β-ol
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis, Cytotoxic Evaluation, and SAR of Epoxysterols

  摘要：

  A library of diastereomerically pure epoxysterols, prepared by combining chemical and enzymatic methodologies, was evaluated for cytotoxicity toward human cancer and noncancer cell lines. Unsaturated steroids were oxidized by magnesium bis(monoperoxyphthal ate) hexahydrate in acetonitrile, and the resulting epimeric epoxides were enzymatically separated using Novozym 435 or lipase AY. Some of the synthesized epoxysterols have potent cytotoxicity and higher activity on cancer cell lines HT29 and LAMA-84.

  DOI：

  10.1021/jm9003973
• 作为产物：
  描述：

  3β-acetoxy-B-norcholest-5-ene 在 MMPP 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以92%的产率得到5α,6α-epoxy-7-nor-5α-cholestan-3β-yl acetate
  参考文献：
  名称：

  使用双（邻过氧化邻苯二甲酸酯）六水合镁高效不饱和类固醇的环氧化

  摘要：

  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。

  DOI：

  10.1016/j.tet.2009.01.100

文献信息

• trans-Hydrindanes by Reduction: Synthesis of Dihydro-B-nortestosterone
  作者：Alexander Kasal、Hana Chodounská、Wojciech J. Szczepek

  DOI：10.1135/cccc19961386

  日期：——

  Reduction with diimide was employed in the synthesis of potential antiandrogens - 17β-hydroxy-B-nor-5α-androstan-3-one (26) and its 17α-methyl derivative (25). Other methods of reduction (hydroboration, catalytic hydrogenation) were less effective.

  使用二亚胺进行还原反应，用于合成潜在的抗雄激素 - 17β-羟基-B-去-5α-雄烷-3-酮（26）及其17α-甲基衍生物（25）。其他还原方法（氢硼化、催化加氢）效果较差。
• Sorm; Dykova, Collection of Czechoslovak Chemical Communications, 1948, vol. 13, p. 407,415
  作者：Sorm、Dykova

  DOI：——

  日期：——
• Joska,J. et al., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 4091 - 4098
  作者：Joska,J. et al.

  DOI：——

  日期：——
• Neurosteroids: 7-aza-allopregnanolone—a poor substitute for allopregnanolone
  作者：Alexander Kasal、Zdena Krištofíková、Miloš Buděšínský

  DOI：10.1016/j.tet.2007.08.078

  日期：2007.11

  7-Nor-20-oxopregn-5-en-3 beta-yl acetate was converted into (20R)-5 beta,6 beta-epoxy-7-nor-5 beta-pregnane-3 beta,20-diyl diacetate in three steps. Stereospecific migration of the 6 alpha-hydride ion led to a 6-oxo derivative with a 5 alpha-configuration. The (Z)- oxime of this ketone underwent Beckmann rearrangement to yield a lactam with the nitrogen in position 7. Lithium aluminium hydride reduction yielded the dihydroxy amine, which was either oxidised or Boc-protected and then oxidised to 7-aza-5 alpha-pregnane-3,20-dione. Its regioselective reduction produced 7-aza-3 alpha- hydroxy-5 alpha-pregnan-20-one-a poor inhibitor for the binding of [S-35] TBPS to the GABA(A) receptor. The corresponding lactam-7-aza3 alpha- hydroxy-5 alpha-pregnane-6,20-dione-was inactive. (C) 2007 Elsevier Ltd. All rights reserved.
• Joska,J. et al., Collection of Czechoslovak Chemical Communications, 1963, vol. 28, p. 82 - 100
  作者：Joska,J. et al.

  DOI：——

  日期：——