4-[N-(4-chlorobenzyl)-N-(4-methylbenzyl)amino]-3-bromobutanenitrile | 942915-26-6

• 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: 4-[N-(4-chlorobenzyl)-N-(4-methylbenzyl)amino]-3-bromobutanenitrile
• 英文别名: 3-Bromo-4-[(4-chlorophenyl)methyl-[(4-methylphenyl)methyl]amino]butanenitrile
• CAS: 942915-26-6
• 化学式: C₁₉H₂₀BrClN₂
• 分子量: 391.738
• InChiKey: UKHHCTGARAKAHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 4-[N-(4-chlorobenzyl)-N-(4-methylbenzyl)amino]-3-bromobutanenitrile 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到4-[N-(4-chlorobenzyl)-N-(4-methylbenzyl)amino]-3-(pyrrolidin-1-yl)butanenitrile
  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
• 作为产物：
  描述：

  2-[1-[(4-Chlorophenyl)methyl]aziridin-2-yl]acetonitrile 、 4-甲基苄溴 以 乙腈 为溶剂， 以74%的产率得到4-[N-(4-chlorobenzyl)-N-(4-methylbenzyl)amino]-3-bromobutanenitrile
  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