N,N-dimethyl-3-amino-3-phenylpropenamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N,N-dimethyl-3-amino-3-phenylpropenamide
• 英文别名: (Z)-3-amino-N,N-dimethyl-3-phenylprop-2-enamide
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: UTKJYIBMJLHZAZ-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-二甲基乙酰胺 、 苯甲腈 在 (diisopropylamino)magnesium 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以87%的产率得到N,N-dimethyl-3-amino-3-phenylpropenamide
  参考文献：
  名称：

  Convenient Direct Synthesis of Vinylogous Urea Derivatives Using Magnesium Amide-induced Amide/Nitrile Coupling

  摘要：

  The magnesium enolates, generated by treatment of acyclic (1) and cyclic tertiary amides (4) with a (diisopropylamino)magnesium reagent, reacted efficiently with nitriles (2) to afford the corresponding beta-aminoacrylamides (3) and alpha-(alpha-aminoalkylidene)lactams (5). The formation of alpha-(2-pyrrolidinylidene)lactams (7) from the reactions of N-methyl-2-pyrrolidone and N-methyl-2-piperidone with a gamma-cyanopropyl p-toluenesulfonate (6) is also described.

  DOI：

  10.3987/com-99-8833

文献信息

• US3970644A
  申请人：——

  公开号：US3970644A

  公开（公告）日：1976-07-20
• Convenient Direct Synthesis of Vinylogous Urea Derivatives Using Magnesium Amide-induced Amide/Nitrile Coupling
  作者：Kazuhiro Kobayashi、Tomohide Kitamura、Ryoji Nakahashi、Akiko Shimizu、Keiichi Yoneda、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.3987/com-99-8833

  日期：——

  The magnesium enolates, generated by treatment of acyclic (1) and cyclic tertiary amides (4) with a (diisopropylamino)magnesium reagent, reacted efficiently with nitriles (2) to afford the corresponding beta-aminoacrylamides (3) and alpha-(alpha-aminoalkylidene)lactams (5). The formation of alpha-(2-pyrrolidinylidene)lactams (7) from the reactions of N-methyl-2-pyrrolidone and N-methyl-2-piperidone with a gamma-cyanopropyl p-toluenesulfonate (6) is also described.