3β,7β-dihydroxy-5β,6β-epoxycholestane | 62073-79-4

• 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: 3β,7β-dihydroxy-5β,6β-epoxycholestane
• 英文别名: 5β,6β-epoxycholestane-3β,7β-diol；5,6β-epoxy-5β-cholestane-3β,7β-diol；5,6β-Epoxy-5β-cholestan-3β,7β-diol；5β,6β-Epoxycholestan-3β,7β-diol；(1S,2R,5S,7S,9R,10R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecane-5,10-diol
• CAS: 62073-79-4
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: NFSVGWISRPLYOZ-POKZUXAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 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：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,7β-dihydroxy-5β,6β-epoxycholestane 在 高氯酸 作用下， 以 丁酮 为溶剂， 生成 5α-cholestane-3β,5,6β,7β-tetrol
  参考文献：
  名称：

  水性分散液中无金属自氧化胆固醇的新产品。

  摘要：

  DOI：

  10.1248/cpb.24.3109
• 作为产物：
  描述：

  5-bromo-5α-cholestane-3β,6β,7β-triol 在 氢氧化钾 作用下， 生成 3β,7β-dihydroxy-5β,6β-epoxycholestane
  参考文献：
  名称：

  Notes - Reaction of NBS with Allylic Alcohols

  摘要：

  DOI：

  10.1021/jo01361a615

文献信息

• <i>J</i>-Based Analysis and DFT-NMR Assignments of Natural Complex Molecules: Application to 3β,7-Dihydroxy-5,6-epoxycholestanes
  作者：Jesús Javier Poza、Carlos Jiménez、Jaime Rodríguez

  DOI：10.1002/ejoc.200800358

  日期：2008.8

  four 3β,7-hydroxy-5,6-epoxycholestanes were easily prepared from cholesterol, and their NMR spectroscopic data were experimentally obtained from 1D and 2D NMR experiments. An exhaustive QM-J-based analysis was then performed to replicate the experimental H–H and C–H coupling constants as well as the 13C NMR chemical shifts. The B3LYP GIAO methodology with the 6-311-G(d,p) basis set was chosen and showed

  为了重现环氧和羟基官能团的立体化学配置，从胆固醇中很容易制备了四种 3β,7-羟基-5,6-环氧胆甾烷，它们的核磁共振光谱数据是从一维和二维核磁共振实验中获得的。然后进行基于 QM-J 的详尽分析以复制实验 H-H 和 C-H 耦合常数以及 13C NMR 化学位移。选择了具有 6-311-G(d,p) 基组的 B3LYP GIAO 方法，并表明从环 A 和 B 获得的数据足以计算 5,6-环氧基和 7-羟基的正确立体化学. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• 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.
• Notes - Reaction of NBS with Allylic Alcohols
  作者：Miguel Romero

  DOI：10.1021/jo01361a615

  日期：1957.10
• A new product of cholesterol by metal-free autoxidation in aqueous dispersion.
  作者：MEIJI KAWATA、MASAHIKO TOHMA、TAKUJI SAWAYA、MICHIYA KIMURA

  DOI：10.1248/cpb.24.3109

  日期：——