1-(1-Ethoxyethenyl)piperidine 1-oxide

• 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-(1-Ethoxyethenyl)piperidine 1-oxide
• 英文别名: 1-(1-Ethoxyethenyl)-1-oxidopiperidin-1-ium
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: PDHLUHQDMHIUSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  27.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-羟基哌啶 、 乙氧基乙炔 以 四氢呋喃 、 正己烷 为溶剂， 反应 72.0h， 生成 1-(1-Ethoxyethenyl)piperidine 1-oxide
  参考文献：
  名称：

  Reverse Cope elimination reactions. 1. Mechanism and scope

  摘要：

  N-4-Pentenyl- and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1,2-dimethylpyrrolidine N-oxide and 1,2-dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of monosubstituted alkenylhydroxylamines to give cyclic hydroxylamines.

  DOI：

  10.1021/jo00123a013

文献信息

• Reverse Cope elimination reactions. 1. Mechanism and scope
  作者：Engelbert Ciganek、John M. Read、Joseph C. Calabrese

  DOI：10.1021/jo00123a013

  日期：1995.9

  N-4-Pentenyl- and N-5-hexenyl-N-methylhydroxylamine cyclized under mild conditions in a reverse Cope elimination reaction to give 1,2-dimethylpyrrolidine N-oxide and 1,2-dimethylpiperidine N-oxide, respectively. The reaction was shown to be concerted and thermodynamically controlled. The scope of this novel cyclization is discussed, and comparisons are made with the closely related and previously reported cyclization of monosubstituted alkenylhydroxylamines to give cyclic hydroxylamines.