3-Anilino-3-(2-methoxyphenyl)-propionsaeurenitril | 145134-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-Anilino-3-(2-methoxyphenyl)-propionsaeurenitril
• 英文别名: 3-(2-methoxyphenyl)-3-(phenylamino)propanenitrile；3-Anilino-3-(2-methoxyphenyl)propionitrile；3-anilino-3-(2-methoxyphenyl)propanenitrile
• CAS: 145134-47-0
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: VXCYRLHNGPJKKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (E)-1-(2-甲氧基苯基)-N-苯基甲亚胺 、 乙腈 在 (三甲基硅基)乙酸乙酯 、 4-甲氧基苯基氧化钠 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以87%的产率得到3-Anilino-3-(2-methoxyphenyl)-propionsaeurenitril
  参考文献：
  名称：

  Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination

  摘要：

  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.

  DOI：

  10.1021/jo802763b

文献信息

• Direct Cyanoalkylation of Imines Driven by a Photoactive Electron Donor–Acceptor Complex
  作者：Wei Liu、Hao Hou、Haochuan Jing、Shiqing Huang、Wei Ou、Chenliang Su

  DOI：10.1021/acs.orglett.4c01673

  日期：2024.7.26

  β-Amino nitriles are important molecular scaffolds. Cyanoalkylation of imines is the most straightforward method for the construction of these scaffolds. In this study, we report the novel cyanoalkylation of imines via radical coupling enabled by a photoactive electron donor–acceptor complex. This strategy is characterized by mild conditions, broad reaction scopes, and high atom economy. The scalability

  β-氨基腈是重要的分子支架。亚胺的氰烷基化是构建这些支架的最直接的方法。在这项研究中，我们报道了通过光敏电子供体-受体复合物实现的自由基偶联实现亚胺的新型氰烷基化。该策略具有条件温和、反应范围广、原子经济性高等特点。该策略的可扩展性和实用性通过 40 g 连续流动系统得到了证明，从中获得了多种重要的药物相关分子。
• Elektrokatalytische Cyanomethylierung von Azomethinen: Eine neue Synthese f�r ?-Aminonitrile
  作者：U. Hess、A.-K. Raasch、M. Schulze

  DOI：10.1002/prac.19923340607

  日期：——

  Certain Schiff-bases (2 - 7) react in acetonitrile (1) at a Hg-cathode in a new electrocatalyzed cyanomethylation method in good yields without side-products to beta-aminonitriles (2a - 7a). The synthesis is initiated by an electrochemical deprotonation of 1 by azomethine-radical anions in catalytical amount to acetonitril anions (B-). During nucleophilic reaction of B- with 2 - 7 up to its complete consumption, the cyanomethylation synthon B- is regenerated in a cyclic, self-reproducing process. Quantum chemical calculation in context with cyanomethylation product analysis permit mechanistical insights and exact prediction of suitable azomethines and coupling position for B-.