2-<(2-methyl-1-phenylpropyl)amino>propanenitrile | 131703-41-8

• 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: 2-<(2-methyl-1-phenylpropyl)amino>propanenitrile
• 英文别名: 2-[(2-methyl-1-phenylpropyl)amino]propanenitrile
• CAS: 131703-41-8；131703-42-9
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: GYENVXCGCBRSNY-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.82
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-甲基-1-苯丙胺 、 氰化钾 、 乙醛 在 sodium hydrogensulfite 作用下， 以 甲醇 、 水 为溶剂， 生成 2-<(2-methyl-1-phenylpropyl)amino>propanenitrile 、 2-<(2-methyl-1-phenylpropyl)amino>propanenitrile
  参考文献：
  名称：

  Thermodynamically controlled 1,3-asymmetric induction in an acyclic system: equilibration of .alpha.-amino nitriles derived from .alpha.-alkylbenzylamines and aldehydes

  摘要：

  Acyclic-alpha-amino nitriles 1, derived from alpha-alkylbenzylamines 3 and aldehydes 4 via a Strecker-type reaction, readily epimerize in MeOH at the newly emerged asymmetric center alpha-to the cyano group. The equilibrium diastereomeric ratio [(R*,R*)-1]:[(R*,S*)-1] varies from 73:27 for le to 90:10 for 1h. The latter ratio is unprecedentedly high for thermodynamically controlled 1,3-asymmetric induction. The aromatic group and a bulky alkyl group (R1) of the parent amine 3 are required to obtain high concentrations of (R*,R*)-1, whereas the bulkiness of the alkyl group (R2) of the parent aldehyde 4 has little effect. The reasons for the thermodynamic predominance of (R*,R*)-1 over (R*,S*)-1 were addressed by MM2 calculations, which predicted the most stable conformers of (R*,R*)-1 and (R*,S*)-1. The structures of these conformers were verified by H-1 NMR spectroscopy and X-ray crystallography.

  DOI：

  10.1021/jo00003a061