3-[2-[1-(6-Methoxynaphthalen-2-yl)ethenyl]pyrrol-1-yl]propanenitrile | 1226779-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[2-[1-(6-Methoxynaphthalen-2-yl)ethenyl]pyrrol-1-yl]propanenitrile
• CAS: 1226779-99-2
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: SBZMPHRCJHTVPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-2-氰乙基吡咯 、 2-乙炔基-6-甲氧基萘 在 十二羰基三钌 、 ammonium hexafluorophosphate 作用下， 以 苯 为溶剂， 以78%的产率得到3-[2-[1-(6-Methoxynaphthalen-2-yl)ethenyl]pyrrol-1-yl]propanenitrile
  参考文献：
  名称：

  Regioselective Formation of α-Vinylpyrroles from the Ruthenium-Catalyzed Coupling Reaction of Pyrroles and Terminal Alkynes Involving C−H Bond Activation

  摘要：

  The cationic ruthenium catalyst Ru-3(CO)(12)/NH4PF6 was found to be highly effective for the intermolecular coupling reaction of pyrroles and terminal alkynes to give gem-selective alpha-vinylpyrroles. The carbon isotope effect on the alpha-pyrrole carbon and the Hammett correlation from a series of para-substituted N-arylpyrroles (rho=-0.90) indicate a rate-limiting C-C bond formation step of the coupling reaction.

  DOI：

  10.1021/jo100269y

文献信息

• Regioselective Formation of α-Vinylpyrroles from the Ruthenium-Catalyzed Coupling Reaction of Pyrroles and Terminal Alkynes Involving C−H Bond Activation
  作者：Ruili Gao、Chae S. Yi

  DOI：10.1021/jo100269y

  日期：2010.5.7

  The cationic ruthenium catalyst Ru-3(CO)(12)/NH4PF6 was found to be highly effective for the intermolecular coupling reaction of pyrroles and terminal alkynes to give gem-selective alpha-vinylpyrroles. The carbon isotope effect on the alpha-pyrrole carbon and the Hammett correlation from a series of para-substituted N-arylpyrroles (rho=-0.90) indicate a rate-limiting C-C bond formation step of the coupling reaction.