N-<5-(5-Methyl-5H-dibenzocycloheptenyl)>-N-methylhydroxylamine | 126899-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: N-<5-(5-Methyl-5H-dibenzocycloheptenyl)>-N-methylhydroxylamine
• 英文别名: N-methyl-N-(2-methyl-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)hydroxylamine
• CAS: 126899-95-4
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: UNQDESDNHPKMOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<5-(5-Methyl-5H-dibenzocycloheptenyl)>-N-methylhydroxylamine 以 氯仿 为溶剂， 反应 2.5h， 生成 5,12-Dimethyl-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine 12-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：

  5-methyl-5H-dibenzocyclohepten-5-ol 、 N-甲基羟胺盐酸盐 在 sodium acetate 、 氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以24%的产率得到N-<5-(5-Methyl-5H-dibenzocycloheptenyl)>-N-methylhydroxylamine
  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 eliminations. Pyrrolidine and piperidine N-oxides by intramolecular addition of N,N-disubstituted hydroxylamines to unactivated double bonds
  作者：Engelbert Ciganek

  DOI：10.1021/jo00297a011

  日期：1990.5
• CIGANEK, ENGELBERT, J. ORG. CHEM., 55,(1990) N0, C. 3007-3009
  作者：CIGANEK, ENGELBERT

  DOI：——

  日期：——
• 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.