3β-chloro-5β,6β-oxidocholestane | 68521-96-0

• 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: 3β-chloro-5β,6β-oxidocholestane
• 英文别名: 3β-chloro-5β,6β-epoxycholestane；(1S,2R,5S,7S,9R,11S,12S,15R,16R)-5-chloro-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecane
• CAS: 68521-96-0
• 化学式: C₂₇H₄₅ClO
• 分子量: 421.107
• InChiKey: STUMUGIDOYWJQH-DTLXENBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 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：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3β-chloro-5β,6β-oxidocholestane 在 吡啶 、 三甲基氯硅烷 作用下， 以 乙醚 为溶剂， 反应 8.25h， 生成 6β-acetoxy-3β,5-dichloro-5α-cholestane
  参考文献：
  名称：

  Husain, Mubarak; Khan, Naseem Hasan, Synthetic Communications, 1981, vol. 11, # 3, p. 185 - 208

  摘要：

  DOI：
• 作为产物：
  描述：

  氯化胆固醇 在 2,4-bisperfluorooctylphenyl butyl selenide 、 水 、 双氧水 作用下， 以 苯 为溶剂， 生成 3β-chloro-5,6α-epoxy-5α-cholestane 、 3β-chloro-5β,6β-oxidocholestane
  参考文献：
  名称：

  A Selenium Catalyzed Epoxidation in Perfluorinated Solvents with Hydrogen Peroxide

  摘要：

  readily prepared 2,4-bisperfluorooctylphenyl butylselenide 催化了在氟相双相体系中用过氧化氢对各种烯烃进行的环氧化反应。该催化剂在全氟化溶剂中具有选择性的溶解性，并且通过相分离可以轻松回收。此外，该催化剂可以重复使用多次，而不会降低产率或延长反应时间。

  DOI：

  10.1055/s-1999-2630

文献信息

• Dichlororuthenium(IV) Complex ofmeso-Tetrakis(2,6-dichlorophenyl)porphyrin: Active and Robust Catalyst for Highly Selective Oxidation of Arenes, Unsaturated Steroids, and Electron-Deficient Alkenes by Using 2,6-DichloropyridineN-Oxide
  作者：Jun-Long Zhang、Chi-Ming Che

  DOI：10.1002/chem.200401008

  日期：2005.6.20

  under acid-free conditions, a wide variety of hydrocarbons including 1) cycloalkenes, conjugated enynes, electron-deficient alkenes (to afford epoxides), 2) arenes (to afford quinones), and 3) Delta5-unsaturated steroids, Delta4-3-ketosteroids, and estratetraene derivatives (to afford epoxide/ketone derivatives of steroids) in up to 99 % product yield within several hours with up to 100 % substrate conversion

  由[Ru（VI）（2,6-Cl2tpp）O2]与Me3SiCl的反应以90％的收率制备的[Ru（IV）（2,6-Cl2tpp）Cl2]是通过X射线晶体学表征的结构明显优于[Ru（IV）（tmp）Cl2]，[Ru（IV）（ttp）Cl2]和[Ru（II）（por）（CO）]（por = 2,6-Cl2tpp，F20-tpp ，F28-tpp）作为烯烃与2,6-Cl2pyNO（2,6-Cl2tpp = meso-tetrakis（2,6-dichlorophenyl）porphyrinato dianion; tmp = meso-tetramesitylporphyrinato dianion; ttp = meso-tetrakis（对甲苯基）卟啉二价阴离子; F20-tpp =间四（五氟苯基）卟啉二价阴离子; F28-tpp = 2,3,7,8,12,13,17,18-八氟-5,10,15
• 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.
• Shafiullah; Ghaffari,M.A., Synthetic Communications, 1979, vol. 9, p. 677 - 682
  作者：Shafiullah、Ghaffari,M.A.

  DOI：——

  日期：——