N-(4-Pentenylidene)methanamine N-oxide | 171819-40-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-(4-Pentenylidene)methanamine N-oxide
• 英文别名: N-methylpent-4-en-1-imine oxide
• CAS: 171819-40-2
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: UHLWRBHQHKZYTL-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-Pentenylidene)methanamine N-oxide 在 lithium aluminium tetrahydride 作用下， 生成 trans-1,2-Dimethylpyrrolidine 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
• 作为产物：
  描述：

  4-戊烯醛 、 N-甲基羟胺盐酸盐 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以83%的产率得到N-(4-Pentenylidene)methanamine N-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