1-Methyl-4-oxo-1-pentadecylpiperidinium trifluoromethanesulfonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-Methyl-4-oxo-1-pentadecylpiperidinium trifluoromethanesulfonate
• 英文别名: 1-Methyl-1-pentadecylpiperidin-1-ium-4-one;trifluoromethanesulfonate
• 化学式: CF₃O₃S*C₂₁H₄₂NO
• 分子量: 473.641
• InChiKey: ANUVBNXCZMZOIC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  正十五胺 在 盐酸 、 甲醇 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 47.0h， 生成 1-Methyl-4-oxo-1-pentadecylpiperidinium trifluoromethanesulfonate
  参考文献：
  名称：

  Catalytic Epoxidation of Alkenes with Oxone

  摘要：

  A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables. A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96% yield.

  DOI：

  10.1021/jo00110a049

文献信息

• Catalytic Epoxidation of Alkenes with Oxone
  作者：Scott E. Denmark、David C. Forbes、David S. Hays、Jeffrey S. DePue、Richard G. Wilde

  DOI：10.1021/jo00110a049

  日期：1995.3

  A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables. A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96% yield.