(Z)-1-Amino-1-(1-naphthyl)-1,3-butadiene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-Amino-1-(1-naphthyl)-1,3-butadiene
• 英文别名: (1Z)-1-naphthalen-1-ylbuta-1,3-dien-1-amine
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: ZFXPGZMGGUDTAU-NSIKDUERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氯丙烯镁 、 氰基萘 在 ammonium hydroxide 作用下， 生成 (E)-1-Amino-1-(1-naphthyl)-1,3-butadiene 、 (Z)-1-Amino-1-(1-naphthyl)-1,3-butadiene
  参考文献：
  名称：

  Preparation of Stable Primary Enamines: 1-Aminobutadienes by Allyl Grignard Addition to Aryl Cyanides Followed by Controlled Hydrolysis

  摘要：

  From thermochemical data it is suggested that 1-aminobutadienes are more stable than their nonconjugated imine tautomers by about 2 kcal mol(-1). High level ab initio calculations have established the thermodynamic preference of the conjugated primary enamines over their beta,gamma-unsaturated ketimine isomers in the gas phase. This general prediction of an increased stability of primary enamines by butadiene conjugation has been confirmed experimentally with a variety of representative examples. Allyl Grignard addition to a number of aryl or hetaryl cyanides followed by controlled hydrolysis yields the respective beta,gamma-unsaturated ketimine systems that subsequently rearrange completely to their 1-aminobutadiene isomers. Rearrangement to the thermodynamically more favored alpha,beta-unsaturated imine tautomers is kinetically inhibited and, hence, not observed in these systems. In some cases conjugated enamine formation is already observed at the stage of the organometallic intermediates.

  DOI：

  10.1021/jo00121a055

文献信息

• Preparation of Stable Primary Enamines: 1-Aminobutadienes by Allyl Grignard Addition to Aryl Cyanides Followed by Controlled Hydrolysis
  作者：Gerhard Erker、Michael Riedel、Sandra Koch、Tim Joedicke、Ernst-Ulrich Wuerthwein

  DOI：10.1021/jo00121a055

  日期：1995.8

  From thermochemical data it is suggested that 1-aminobutadienes are more stable than their nonconjugated imine tautomers by about 2 kcal mol(-1). High level ab initio calculations have established the thermodynamic preference of the conjugated primary enamines over their beta,gamma-unsaturated ketimine isomers in the gas phase. This general prediction of an increased stability of primary enamines by butadiene conjugation has been confirmed experimentally with a variety of representative examples. Allyl Grignard addition to a number of aryl or hetaryl cyanides followed by controlled hydrolysis yields the respective beta,gamma-unsaturated ketimine systems that subsequently rearrange completely to their 1-aminobutadiene isomers. Rearrangement to the thermodynamically more favored alpha,beta-unsaturated imine tautomers is kinetically inhibited and, hence, not observed in these systems. In some cases conjugated enamine formation is already observed at the stage of the organometallic intermediates.