3-((4-methoxyphenyl)amino)-2-methyl-3-phenylpropanenitrile | 959042-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-((4-methoxyphenyl)amino)-2-methyl-3-phenylpropanenitrile
• 英文别名: 2-methyl-3-phenyl-3-(4-methoxyphenylamino)propanenitrile；3-(4-Methoxy-phenylamino)-2-methyl-3-phenyl-propionitrile；3-(4-methoxyanilino)-2-methyl-3-phenylpropanenitrile
• CAS: 959042-54-7
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: SOYIJDCTBAZTCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-亚苄基-4-甲氧基苯胺 、 丙腈 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 以50%的产率得到3-((4-methoxyphenyl)amino)-2-methyl-3-phenylpropanenitrile
  参考文献：
  名称：

  Base-Controlled Diastereoselective Synthesis of Either anti- or syn-β-Aminonitriles

  摘要：

  Deprotonation of secondazty alkane nitriles with nBuLi and addition to aryl imines gives kinetic anti-beta-aminonitriles. Use of LHMDS allows reversible protonation of the reaction intermediate to give syn-beta-aminoriitriles. The pure diastereosiomers can be isolated in good yields, and the mechanism was elucidated.

  DOI：

  10.1021/acs.orglett.7b00679

文献信息

• Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination
  作者：Thomas Poisson、Vincent Gembus、Sylvain Oudeyer、Francis Marsais、Vincent Levacher

  DOI：10.1021/jo802763b

  日期：2009.5.1

  The first transition-metal-free addition of alkyl nitriles to unactivated irnines was developed using a catalytic combination of 4-MeOC6H4CNa and TMSCH2CO2Et to promote the reaction. The corresponding beta-amino nitriles are obtained in good to almost quantitative isolated yields under mild conditions. A mechanism involving an autocatalytic pathway is proposed on the basis of experimental observations.