(4,5)β-epoxy-5β-cholestan-3β-ol | 20220-27-3

• 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: (4,5)β-epoxy-5β-cholestan-3β-ol
• 英文别名: 4β,5 β-epoxycholestan-3β-ol；4β,5β-epoxycholestan-3β-ol；4β,5-epoxy-5β-cholestan-3β-ol；(1S,2R,5S,6S,8R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadecan-5-ol
• CAS: 20220-27-3
• 化学式: C₂₇H₄₆O₂
• 分子量: 402.661
• InChiKey: AJIBEBUBGLMKAS-JIGCPDEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4,5)β-epoxy-5β-cholestan-3β-ol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 Chloro-5α-cholestandiol-3β,4β
  参考文献：
  名称：

  Lorne,R.; Julia,S., Bulletin de la Societe Chimique de France, 1973, p. 1357 - 1368

  摘要：

  DOI：
• 作为产物：
  描述：

  4-胆甾烯-3-酮 在 甲醇 、 sodium hydroxide 、 乙醚 、 乙醇 、 双氧水 、 铂 作用下， 生成 (4,5)β-epoxy-5β-cholestan-3β-ol
  参考文献：
  名称：

  关于类固醇和性激素。155。约3α，5-二氧-邻前列腺素和两个差向异构的3,4-二氧-胆甾烷

  摘要：

  通过胆甾醇环氧化物的催化还原，可以以部分合成的方式制备3α，5-二氧-共前列腺素，其在不对称中心5的空间排列上对应于司他啡啶和相关糖苷配基的构型。

  DOI：

  10.1002/hlca.19480310647

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。
• Circular dichroism of some optically active steroidal iodides
  作者：R. C. Cookson、J. M. Coxon

  DOI：10.1039/j39710001466

  日期：——

  A series of steroid iodides show the expected absorption maximum at 260–270 nm in their u.v. spectra, and a corresponding maximum in their circular dichroism curves at slightly shorter wavelengths, the sign of which for the secondary iodides usually agrees with that recently reported for alkyl iodides. However, adjacent hetero-substituents or unsaturation may reverse the sign.

  一系列类固醇碘化物在uv光谱中显示在260-270 nm处具有预期的最大吸收，在稍短的波长处其圆二色性曲线中也具有相应的最大吸收，其中次级碘化物的符号通常与最近报道的烷基碘相符碘化物。但是，相邻的杂取代基或不饱和键可能会使符号反转。
• Atypical regioselective biohydrolysis on steroidal oxiranes by Aspergillus niger whole cells: Some stereochemical features
  作者：Fabricio R. Bisogno、Alejandro A. Orden、Celeste Aguirre Pranzoni、Diego A. Cifuente、Oscar S. Giordano、Marcela Kurina Sanz

  DOI：10.1016/j.steroids.2007.04.003

  日期：2007.7

  5,6-Epoxycholestan-3 beta-ol derivatives were hydrolyzed in a diastereoconvergent manner by growing and resting cells of several strains of Aspergillus niger, particularly A. niger ATCC 11394. These strains displayed opposite regioselectivity toward each isomer in an a and P epoxide mixture, thus, the nucleophilic attack took place at the less substituted and the most substituted carbon atom on each diasteromer, respectively These biocatalysts opened trisubstituted oxiranes but were unable to hydrolyze the disubstituted oxiranes in the tested sterol derivatives. These findings suggest that A. niger strains possess another hydrolytic ability different from the commercial A. niger epoxide hydrolase (EH) that did not accept this kind of steroidal oxiranes as substrates. (c) 2007 Elsevier Inc. All rights reserved.
• Efficient Chemoenzymatic Synthesis, Cytotoxic Evaluation, and SAR of Epoxysterols
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm9003973

  日期：2009.7.9

  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.
• Steric control of epoxidation by carbamate and amide groups. Evidence for the carbonyl-directed epoxidation
  作者：Pavel Kocovsky、Ivo Stary

  DOI：10.1021/jo00297a047

  日期：1990.5