1-Nonyl-4-oxo-piperidine-3-carboxylic acid methyl ester | 167279-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Nonyl-4-oxo-piperidine-3-carboxylic acid methyl ester
• 英文别名: Methyl 1-nonyl-4-oxo-3-piperidinecarboxylate；methyl 1-nonyl-4-oxopiperidine-3-carboxylate
• CAS: 167279-51-8
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: MMXDFYIJUSDGEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Nonyl-4-oxo-piperidine-3-carboxylic acid methyl ester 在 盐酸 作用下， 反应 15.0h， 以49%的产率得到1-nonyl-piperidin-4-one (N-nonyl-4-piperidone)
  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
• 作为产物：
  描述：

  3-[(2-Methoxycarbonyl-ethyl)-nonyl-amino]-propionic acid methyl ester 在 甲醇 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 4.0h， 以89%的产率得到1-Nonyl-4-oxo-piperidine-3-carboxylic acid methyl ester
  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.