(Z)-N,N-dimethyl-2-[2-phenyl-2-(4-N,N-dimethylaminophenyl)ethenyloxy]ethanamine

• 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: (Z)-N,N-dimethyl-2-[2-phenyl-2-(4-N,N-dimethylaminophenyl)ethenyloxy]ethanamine
• 英文别名: 4-[(Z)-2-[2-(dimethylamino)ethoxy]-1-phenylethenyl]-N,N-dimethylaniline
• 化学式: C₂₀H₂₆N₂O
• 分子量: 310.439
• InChiKey: FGZQQTKGXIDJGB-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴-N,N-二甲基苯胺 、 N,N-dimethyl-2-[2-(phenyl)ethenyloxy]ethanamine 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) sodium acetate 、 potassium carbonate 、 lithium chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 N,N-dimethyl-2-[2-phenyl-1-(4-N,N-dimethylaminophenyl)ethenyloxy]ethanamine 、 (Z)-N,N-dimethyl-2-[2-phenyl-2-(4-N,N-dimethylaminophenyl)ethenyloxy]ethanamine 、 (E)-N,N-dimethyl-2-[2-phenyl-2-(4-N,N-dimethylaminophenyl)ethenyloxy]ethanamine
  参考文献：
  名称：

  Microwave-Promoted and Chelation-Controlled Double Arylations of Terminal Olefinic Carbon of Vinyl Ethers

  摘要：

  Herein we report a rapid, palladium-catalyzed terminal diarylation of the chelating olefin N,N-dimethyl(2-ethenyloxy)ethanamine under noninert conditions utilizing controlled microwave heating as a convenient energy source. Among the aryl bromides examined, both electron-rich and electron-poor substrates were demonstrated to furnish useful yields after only 10-120 min of directed microwave heating at 160-200 degreesC. The good terminal regioselectivity suggests that the precatalyst (Herrmann's palladacycle) serves as a source of weakly coordinated palladium(0) in the investigated high-temperature Heck process.

  DOI：

  10.1021/jo035815f

文献信息

• Microwave-Promoted and Chelation-Controlled Double Arylations of Terminal Olefinic Carbon of Vinyl Ethers
  作者：Andreas Svennebring、Peter Nilsson、Mats Larhed

  DOI：10.1021/jo035815f

  日期：2004.5.1

  Herein we report a rapid, palladium-catalyzed terminal diarylation of the chelating olefin N,N-dimethyl(2-ethenyloxy)ethanamine under noninert conditions utilizing controlled microwave heating as a convenient energy source. Among the aryl bromides examined, both electron-rich and electron-poor substrates were demonstrated to furnish useful yields after only 10-120 min of directed microwave heating at 160-200 degreesC. The good terminal regioselectivity suggests that the precatalyst (Herrmann's palladacycle) serves as a source of weakly coordinated palladium(0) in the investigated high-temperature Heck process.