2,3α-epoxy-5α-cholestan-6-one | 20281-58-7

• 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: 2,3α-epoxy-5α-cholestan-6-one
• 英文别名: 2,3-epoxy-5α-cholestan-6-one；2α,3α-epoxy-5α-cholestan-6-one；2α,3α-Epoxy-5α-cholestan-6-on；(1S,2R,4R,6S,8S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-9-one
• CAS: 20281-58-7
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: DEGMOIUJNNXOFD-AYFCCLHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3α-epoxy-5α-cholestan-6-one 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 乙醚 、 溶剂黄146 作用下， 生成 (5alpha)-胆甾烷-3,6-二酮
  参考文献：
  名称：

  330.类固醇。第二部分 的制备外延胆固醇氯化物和溴化物

  摘要：

  DOI：

  10.1039/jr9520001790
• 作为产物：
  描述：

  5α-cholest-2-en-6-one 在 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以66%的产率得到2,3α-epoxy-5α-cholestan-6-one
  参考文献：
  名称：

  Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy-5α-cholestan-6-one

  摘要：

  Disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was evaluated and compared to that of disodium 2 beta,3 alpha-dihydroxy-5 alpha-cholestane disulfate (10) and diols 7 and 9. Compounds 8 and 10 were active with IC50 values of 14.59 and 59.65 mu M. respectively. Diols 7 and 9 showed no inhibitory activity (IC50 > 500 mu M). (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.005

文献信息

• Selective Epoxidation of Olefins by Perfluoro-<i>cis</i>-2,3-dialkyloxaziridines¹
  作者：Alberto Arnone、Darryl D. DesMarteau、Barbara Novo、Viacheslav A. Petrov、Massimo Pregnolato、Giuseppe Resnati

  DOI：10.1021/jo961196h

  日期：1996.1.1

  Alkyl-substituted olefins are epoxidized by perfluoro-cis-2,3-dialkyloxaziridines under particularly mild conditions. Electron deficient substrates (e.g, alpha,beta-enones) can also be epoxidized, and the more electron poor the double bond is, the more severe the reactions conditions become. The epoxidation is chemoselective (secondary alcohols and their ethers do not interfere), site selective (the monoepoxide of a diene can be obtained), and stereoselective (cis-alkenes afford cis-epoxides). Various complex and polyfunctional substrates of natural origin (monoterpenes, sesquiterpenes, steroids) have been transformed effectively.
• On steroids CXIII. Sterilizing effect of some 6-ketosteroids on housefly /Musca domestica L./
  作者：B REABOVA、J HORA、V LANDA、V CERNY、F SORM

  DOI：10.1016/s0039-128x(68)80063-7

  日期：1968.4
• Shiota; Mori, Nippon Kagaku Zasshi, 1955, vol. 76, p. 1192
  作者：Shiota、Mori

  DOI：——

  日期：——