(2Z)-4-[N-(4-methylbenzyl)-N-benzylamino]-2-butenenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z)-4-[N-(4-methylbenzyl)-N-benzylamino]-2-butenenitrile
• 英文别名: (Z)-4-[benzyl-[(4-methylphenyl)methyl]amino]but-2-enenitrile
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: ARRDGBZJIOXWHN-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(cyanomethyl)-1-(4-methylbenzyl)aziridine 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 (2Z)-4-[N-(4-methylbenzyl)-N-benzylamino]-2-butenenitrile
  参考文献：
  名称：

  Novel Synthesis of 3,4-Diaminobutanenitriles and 4-Amino-2-butenenitriles from 2-(Cyanomethyl)aziridines through Intermediate Aziridinium Salts:  An Experimental and Theoretical Approach

  摘要：

  1-Arylmethyl-2-(cyanomethyl)aziridines were transformed into 4-(N,N-bis(arylmethyl)amino)-3-(pyrrolidin-1-yl)butanenitriles and 4-(N,N-bis(arylmethyl)amino)-2-butenenitriles via 4-(N,N-bis(arylmethyl)amino)-3-bromobutanenitriles in high yields and purity. The key steps involve the unprecedented regiospecific ring opening of intermediate 2-(cyanomethyl)aziridinium salts by bromide and pyrrolidine in acetonitrile, exclusively at the substituted aziridine carbon atom. The results were rationalized on the basis of ab initio calculations.

  DOI：

  10.1021/jo0704210

文献信息

• Novel Synthesis of 3,4-Diaminobutanenitriles and 4-Amino-2-butenenitriles from 2-(Cyanomethyl)aziridines through Intermediate Aziridinium Salts:  An Experimental and Theoretical Approach
  作者：Matthias D'hooghe、Veronique Van Speybroeck、Andries Van Nieuwenhove、Michel Waroquier、Norbert De Kimpe

  DOI：10.1021/jo0704210

  日期：2007.6.1

  1-Arylmethyl-2-(cyanomethyl)aziridines were transformed into 4-(N,N-bis(arylmethyl)amino)-3-(pyrrolidin-1-yl)butanenitriles and 4-(N,N-bis(arylmethyl)amino)-2-butenenitriles via 4-(N,N-bis(arylmethyl)amino)-3-bromobutanenitriles in high yields and purity. The key steps involve the unprecedented regiospecific ring opening of intermediate 2-(cyanomethyl)aziridinium salts by bromide and pyrrolidine in acetonitrile, exclusively at the substituted aziridine carbon atom. The results were rationalized on the basis of ab initio calculations.