3-(2-cyanophenyl)-N,N-dimethylpropanamide

• 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: 3-(2-cyanophenyl)-N,N-dimethylpropanamide
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: LQOLBPTZHHLVSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻氯苯腈 、 N,N-dimethyl-3-(trifluoro-λ⁴-boranyl)propanamide potassium salt 在 palladium diacetate 、 potassium carbonate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 、 甲苯 为溶剂， 反应 14.0h， 以83%的产率得到3-(2-cyanophenyl)-N,N-dimethylpropanamide
  参考文献：
  名称：

  Use of Potassium β-Trifluoroborato Amides in Suzuki−Miyaura Cross-Coupling Reactions

  摘要：

  Potassium beta-trifluoroborato amides were prepared and used as successful partners in Suzuki-Miyaura reactions with various aryl chlorides, including electron-rich and electron-poor derivatives, as well as several heteroaryl chloride partners.

  DOI：

  10.1021/jo900968h

文献信息

• Radical cyclisation onto nitriles
  作者：W.Russell Bowman、Colin F Bridge、Philip Brookes

  DOI：10.1016/s0040-4039(00)01596-3

  日期：2000.11

  Iminyl radicals, generated by 5-exo cyclisation of alkyl, vinyl and aryl C-centred radicals onto nitriles, undergo β-scission (nitrile translocation), reduction or tandem cyclisation onto alkenes depending on the nature of the α-substituent. 5-exo Cyclisations of aryl radicals onto nitriles undergo nitrile translocation when the α-substituent is CN, CO2R, SO2Ph or CONMe2. The rate of translocation

  通过将烷基，乙烯基和芳基C中心的自由基进行5 exo环化到腈上而生成的亚氨基自由基，根据α取代基的性质，经历β断裂（腈移位），还原或串联环化到烯烃上。当α-取代基为CN，CO 2 R，SO 2 Ph或CONMe 2时，芳基在腈上的5- exo环化经历腈移位。易位的速率快于5-或6- exo环化到烯烃上或烯丙基氢的1,5-氢提取上。当α-取代基为烷基时，中间体亚氨基不经历腈移位。
• Use of Potassium β-Trifluoroborato Amides in Suzuki−Miyaura Cross-Coupling Reactions
  作者：Gary A. Molander、Ludivine Jean-Gérard

  DOI：10.1021/jo900968h

  日期：2009.8.7

  Potassium beta-trifluoroborato amides were prepared and used as successful partners in Suzuki-Miyaura reactions with various aryl chlorides, including electron-rich and electron-poor derivatives, as well as several heteroaryl chloride partners.