N-((E)-2-Hexen-1-yl)-N-methyl-3-methoxyaniline | 150596-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-((E)-2-Hexen-1-yl)-N-methyl-3-methoxyaniline
• 英文别名: N-[(E)-hex-2-enyl]-3-methoxy-N-methylaniline
• CAS: 150596-81-9
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: TUOGTDHWMIZBHX-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-((E)-2-Hexen-1-yl)-N-methyl-3-methoxyaniline 在 zinc(II) chloride 作用下， 生成 N-Methyl-4-((E)-2-hexen-1-yl)-3-methoxyaniline
  参考文献：
  名称：

  Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allylanilines

  摘要：

  The 3-aza-Cope rearrangement of N-alkyl-N-allylaniline substrates, which required 250-degrees-C to proceed thermally, was promoted by Lewis acid reagents at 111-140-degrees-C. Systematic studies of this reaction were performed to examine a number of reaction variables such as concentration, the stoichiometry of the Lewis acid with the substrate, the optimum temperature for rearrangement, and the type of Lewis acid reagent. Of the many Lewis acids investigated, ZnCl2 (140-degrees-C) and Et2O.BF3 (111-degrees-C) were the most generally successful reagents for promoting the aromatic 3-aza-Cope rearrangement. With respect to substrate variation, the presence of a methoxy substituent para to the N-allyl group slowed the reaction slightly, while a meta substituent accelerated the rate of [3,3] rearrangement and produced moderate site selectivity on the aromatic ring. Lewis acid-promoted rearrangement of an unsymmetrically substituted allyl moiety resulted in [3,3] sigmatropic rearrangement to give the 1-hexen-3-yl substituent on the aromatic ring. Overall, both ZnCl2 and Et2O.BF3 were shown to efficiently accelerate the regiospecific 3-aza-Cope rearrangement of N-alkyl-N-allylanilines for the purpose of forming a carbon-carbon bond between a secondary alkyl substituent and an aromatic ring.

  DOI：

  10.1021/jo00071a018
• 作为产物：
  描述：

  2-己烯醇 在 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 N-((E)-2-Hexen-1-yl)-N-methyl-3-methoxyaniline
  参考文献：
  名称：

  Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allylanilines

  摘要：

  The 3-aza-Cope rearrangement of N-alkyl-N-allylaniline substrates, which required 250-degrees-C to proceed thermally, was promoted by Lewis acid reagents at 111-140-degrees-C. Systematic studies of this reaction were performed to examine a number of reaction variables such as concentration, the stoichiometry of the Lewis acid with the substrate, the optimum temperature for rearrangement, and the type of Lewis acid reagent. Of the many Lewis acids investigated, ZnCl2 (140-degrees-C) and Et2O.BF3 (111-degrees-C) were the most generally successful reagents for promoting the aromatic 3-aza-Cope rearrangement. With respect to substrate variation, the presence of a methoxy substituent para to the N-allyl group slowed the reaction slightly, while a meta substituent accelerated the rate of [3,3] rearrangement and produced moderate site selectivity on the aromatic ring. Lewis acid-promoted rearrangement of an unsymmetrically substituted allyl moiety resulted in [3,3] sigmatropic rearrangement to give the 1-hexen-3-yl substituent on the aromatic ring. Overall, both ZnCl2 and Et2O.BF3 were shown to efficiently accelerate the regiospecific 3-aza-Cope rearrangement of N-alkyl-N-allylanilines for the purpose of forming a carbon-carbon bond between a secondary alkyl substituent and an aromatic ring.

  DOI：

  10.1021/jo00071a018