N,N-dimethyl-2-[2-(2-naphthyl)ethenyloxy]ethanamine | 199595-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-dimethyl-2-[2-(2-naphthyl)ethenyloxy]ethanamine
• 英文别名: N,N-dimethyl-2-(2-naphthalen-2-ylethenoxy)ethanamine
• CAS: 199595-29-4
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: VBDYDRFRTIITQL-UHFFFAOYSA-N

物化性质

• 沸点：
  377.2±25.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴苯 、 N,N-dimethyl-2-[2-(2-naphthyl)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 0.25h， 生成 N,N-dimethyl-2-[(1-phenyl-2-(2-naphthyl))ethenyloxy]ethanamine 、 (Z)-N,N-dimethyl-2-[(2-phenyl-2-(2-naphthyl))ethenyloxy]ethanamine 、 (E)-N,N-dimethyl-2-[(2-phenyl-2-(2-naphthyl))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
• 作为产物：
  描述：

  B-二甲胺基乙基 乙烯基 醚 、 2-溴萘 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 0.25h， 以85%的产率得到N,N-dimethyl-2-[2-(2-naphthyl)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

• Method for organic reactions
  申请人：Labwell AB

  公开号：US06136157A1

  公开（公告）日：2000-10-24

  Organic reactions catalyzed by palladium, except Pd/C, are conducted with heating by microwave energy. The preferred inorganic reactions involved are coupling reactions in which a new carbon-carbon bond is formed. Preferred reactions are the Heck, Stille and Suzuki reaction. The method provides high yields in very short reaction times.

  除了Pd/C之外，由钯催化的有机反应是通过微波能量加热进行的。所涉及的优选无机反应是偶联反应，其中形成了新的碳-碳键。优选反应包括Heck反应，Stille反应和Suzuki反应。该方法在非常短的反应时间内提供高收率。
• Microwave-Promoted Palladium-Catalyzed Coupling Reactions
  作者：Mats Larhed、Anders Hallberg

  DOI：10.1021/jo9612990

  日期：1996.1.1
• Larhed, Mats; Andersson, Carl-Magnus; Hallberg, Anders, Acta Chemica Scandinavica, 1993, vol. 47, # 2, p. 212 - 217
  作者：Larhed, Mats、Andersson, Carl-Magnus、Hallberg, Anders

  DOI：——

  日期：——
• 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.