3-(4-fluorophenyl)-4-phenyl-1H-pyrrole | 1398057-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(4-fluorophenyl)-4-phenyl-1H-pyrrole
• CAS: 1398057-68-5
• 化学式: C₁₆H₁₂FN
• 分子量: 237.276
• InChiKey: NGWWNCPOOJBNPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(1-叠氮乙烯基)-4-氟苯 、 苯乙醛 在 nickel dichloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以77%的产率得到3-(4-fluorophenyl)-4-phenyl-1H-pyrrole
  参考文献：
  名称：

  2,4- vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts

  摘要：

  A novel and efficient copper or nickel catalyzed highly selective denitrogenative annulation of vinyl azides with aryl acetaldehydes has been developed. 2,4- and 3,4-diaryl substituted pyrroles, which are difficult to synthesize by the reported methods, can be highly regioselectively prepared by this protocol simply switched by the selection of the transition metal catalysts. Compared with the reported acidic or basic conditions for polysubstituted pyrrole synthesis, the present reaction conditions are mild, neutral, and very simple without any additives.

  DOI：

  10.1021/ol302270z

文献信息

• 2,4- vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts
  作者：Feng Chen、Tao Shen、Yuxin Cui、Ning Jiao

  DOI：10.1021/ol302270z

  日期：2012.9.21

  A novel and efficient copper or nickel catalyzed highly selective denitrogenative annulation of vinyl azides with aryl acetaldehydes has been developed. 2,4- and 3,4-diaryl substituted pyrroles, which are difficult to synthesize by the reported methods, can be highly regioselectively prepared by this protocol simply switched by the selection of the transition metal catalysts. Compared with the reported acidic or basic conditions for polysubstituted pyrrole synthesis, the present reaction conditions are mild, neutral, and very simple without any additives.