trans-vaccenic acid methyl ester 11,12-oxide | 38520-28-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-vaccenic acid methyl ester 11,12-oxide
• 英文别名: trans-11,12-Epoxy-octadecancarbonsaeuremethylester；Methyl 10-[(2S,3S)-3-hexyloxiran-2-yl]decanoate
• CAS: 38520-28-4；38520-29-5；67101-30-8；126571-20-8
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: MSZLFFUXXWLIRE-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式-11-十八烯酸甲酯 在 perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以70%的产率得到trans-vaccenic acid methyl ester 11,12-oxide
  参考文献：
  名称：

  Selective Epoxidation of Olefins by Perfluoro-cis-2,3-dialkyloxaziridines¹

  摘要：

  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.

  DOI：

  10.1021/jo961196h

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.