5α-cholest-2-en-6α-ol | 28398-76-7

• 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-cholest-2-en-6α-ol
• 英文别名: (5S,6S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-ol
• CAS: 28398-76-7
• 化学式: C₂₇H₄₆O
• 分子量: 386.662
• InChiKey: JBVRHPMPWKLVCJ-UGQJNTJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5α-cholest-2-en-6α-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 2β-Acetoxy-3β-hydroxy-5α-cholestanon-6
  参考文献：
  名称：

  Synthesis of analogs of α-ecdysone. A simplified synthesis of 2β,3β,14α-trihydroxy-7-en-6-one-5β-steroids

  摘要：

  DOI：

  10.1016/s0039-128x(70)80099-x
• 作为产物：
  描述：

  5α-cholest-2-en-6-one 在 丙醇 、 sodium 作用下， 以 丙醇 为溶剂， 以90%的产率得到5α-cholest-2-en-6α-ol
  参考文献：
  名称：

  Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies

  摘要：

  Disulfated and trisulfated steroids have been synthesized from cholesterol and their acetylcholinesterase inhibitory activity has been evaluated. In our studies we have found that the activity was not only dependent on the location of the sulfate groups but on their configurations. 2 beta,3 alpha,6 alpha-trihydroxy-5 alpha-cholestan-6-one trisulfate (18) was the most active steroid with an IC50 value of 15.48 mu M comparable to that of 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one disulfate (1). Both compounds were found to be less active than the reference compound eserine. The butyrylcholinesterase activity of 1 and 18 was one magnitude lower than that against acetylcholinesterase revealing a selective inhibitor profile. (C) 2013 Elsevier Inc.

  DOI：

  10.1016/j.steroids.2013.08.003

文献信息

• Potassium borohydride reductions of immobilised ketosteroids
  作者：Josie C Briggs、Philip Hodge、Zhengpu Zhang

  DOI：10.1016/s0040-4020(97)00011-2

  日期：1997.3

  insoluble supports (powdered polyethylene, microporous 2% crosslinked polystyrene beads, macroporous highly crosslinked polystyrene beads, silica gel and alumina) can be reduced using aqueous potassium borohydride. The use of phase transfer catalysts generally raises yields. In the case of 6-ketosteriods the supported reactions often follow a stereochemical course significantly different from that of

  可以使用硼氢化钾水溶液还原吸收到各种不溶性载体（粉状聚乙烯，2％交联的微孔聚苯乙烯微珠，大孔高度交联的聚苯乙烯微珠，硅胶和氧化铝）中的酮类固醇。相转移催化剂的使用通常提高产率。对于6-酮类化合物，所支持的反应通常遵循的立体化学过程与溶液中类似反应的显着不同。这归因于类固醇在载体内表面上的吸附。在这些情况下，基本上抑制了烷氧基硼氢化物对酮类固醇的还原，因此大部分还原是由BH 4-引起的。本身是一种相对空间上不需要的还原剂。最终结果是，尽管硼氢化钾可将溶液中的6-酮类固醇还原成15:85的6α-和6β-醇，但负载的类固醇的比例可高达90:10。
• Potassium borohydride reductions of ketones absorbed into polymer supports: stereochemical effects
  作者：Josie C. Briggs、Philip Hodge

  DOI：10.1039/c39880000310

  日期：——

  The proportions of 6α-alcohol obtained from aqueous potassium borohydride reductions of 3β-hydroxy-5α-cholestan-6-one (1) absorbed into various polymers varied from 0 to 90% depending on the polymer used and whether or not a phase transfer catalyst was added; some other ketones show similar stereochemical effects, the greatest effects probably arising when the substrates are adsorbed to the inner surfaces

  由硼氢化钾水溶液还原3β-羟基-5α-胆甾醇-6-一（1）吸收而得的6α-醇的比例在0至90％之间变化，具体取决于所用的聚合物以及是否使用相转移催化剂加入; 其他一些酮类化合物也显示出相似的立体化学效应，当底物吸附在适当聚合物的内表面上时，最大的效应可能会出现。
• 647. Steroids and walden inversion. Part VII. The stereochemistry and the mechanism of the i-steroid rearrangement
  作者：C. W. Shoppee、G. H. R. Summers

  DOI：10.1039/jr9520003361

  日期：——
• BRIGGS, JOSIE C.;HODGE, PHILIP, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 4, 310-311
  作者：BRIGGS, JOSIE C.、HODGE, PHILIP

  DOI：——

  日期：——
• Synthesis of analogs of α-ecdysone. A simplified synthesis of 2β,3β,14α-trihydroxy-7-en-6-one-5β-steroids
  作者：Malcolm J. Thompson、William E. Robbins、John N. Kaplanis、Charles F. Cohen、Stanton M. Lancaster

  DOI：10.1016/s0039-128x(70)80099-x

  日期：1970.7