3β-chloro-5,6β-dihydroxy-5α-cholestane | 53531-23-0

• 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-5,6β-dihydroxy-5α-cholestane
• 英文别名: 3β-chloro-5α,6β-dihydroxycholestane；3β-chloro-5α-cholestane-5,6β-diol；3β-chlorocholestan-5α,6β-diol；3β-Chlor-5α-cholestan-5,6β-diol；3β-Chlor-cholestan-5α,6β-diol；3β-Chloro-5α,6β-cholestandiol；3b-Chloro-5a-cholestan-5,6b-diol；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-3-chloro-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-5,6-diol
• CAS: 53531-23-0
• 化学式: C₂₇H₄₇ClO₂
• 分子量: 439.122
• InChiKey: QVYBGWRRVUFCLI-RUXQDQFYSA-N

物化性质

• 沸点：
  514.8±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-chloro-5,6β-dihydroxy-5α-cholestane 在 sodium hydroxide 、 高氯酸 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 cholestane-3α,5α,6β-triol
  参考文献：
  名称：

  A MULTIGRAM PREPARATIVE SYNTHESIS OF CHOLEST-4-EN-3α,6β- AND -3α,6α-DIOLS

  摘要：

  A preparative synthesis of cholest-4-en-3 alpha ,6 beta- and -3 alpha ,6 beta -diols 10 and 15 using cheap reagents and simple working-up procedures without chromatography on a multigram scale is described.

  DOI：

  10.1081/scc-100105387
• 作为产物：
  描述：

  3β-chloro-5,6α-epoxy-5α-cholestane 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 20.0h， 生成 3β-chloro-5,6β-dihydroxy-5α-cholestane
  参考文献：
  名称：

  Reaction of 3β-chloro-5α,6α-epoxysteroids with trifluoroacetic acid

  摘要：

  It has been established that on the interaction of the 5 alpha, 6 alpha-eponysteroids (1a-c) with trifluoroacetic acid in chloroform the 6-trifluoroacetates of the 5 alpha,6 beta-diols (2a-c) are formed in high yield. The alkaline hydrolysis of the trifluoroacetates (2a-c) leads to the corresponding diols (3a-c).

  DOI：

  10.1007/bf02234929

文献信息

• Applications of chromous chloride—II
  作者：J.R. Hanson、E. Premuzic

  DOI：10.1016/s0040-4020(01)97921-9

  日期：1967.1

  The reduction by chromous chloride of 6-nitrocholesteryl acetate and some 5α-chloro-6β-nitro-steroids to 5α-hydroxy-6-oximino steroids is described.

  描述了用氯化铬将乙酸6-硝基胆固醇酯和一些5α-氯-6β-硝基甾族化合物还原为5α-羟基-6-肟基甾族化合物。
• 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.
• Synthesis of aminosterols and their derivatives
  作者：Shafiullah、R.K. Singh、Malik Jamaluddin、H. Ogura、H. Takayanagi

  DOI：10.1016/0039-128x(90)90007-x

  日期：1990.3

  Reactions of steroidal epoxides such as 5,6 alpha-epoxy-5 alpha-cholestane (I) and its 3 beta-chloro (II) and 3 beta-acetoxy (III) analogs with urea in dimethylformamide afforded 6 beta-amino-5 alpha-cholestan-5-ol (IV-VI), 6 beta-amino-N-formyl-5 alpha-cholestan-5-ol (VII-IX), and 6 beta-amino-N-amido-5 alpha-cholestan-5-ol (X-XII), along with the 5 alpha-cholestane-5,6 beta-diol (XIII-XV). In addition to these compounds, the 3 beta-acetoxy analog also afforded the N-carboxyl derivative (XVI).
• Shoppee et al., Journal of the Chemical Society, 1956, p. 2492,2497
  作者：Shoppee et al.

  DOI：——

  日期：——
• Shafiullah; Jamaluddin, Malik; Siddiqui, Ishrat H, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 7, p. 700 - 701
  作者：Shafiullah、Jamaluddin, Malik、Siddiqui, Ishrat H、Ogura, H、Takayanagi, H

  DOI：——

  日期：——

表征谱图