N-benzoyl-2-(2-bromopyridin-3-yl)-3-(1-phenylvinyl)-2,5-dihydro-1H-pyrrole | 1428883-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-benzoyl-2-(2-bromopyridin-3-yl)-3-(1-phenylvinyl)-2,5-dihydro-1H-pyrrole
• 英文别名: [2-(2-Bromopyridin-3-yl)-3-(1-phenylethenyl)-2,5-dihydropyrrol-1-yl]-phenylmethanone
• CAS: 1428883-62-8
• 化学式: C₂₄H₁₉BrN₂O
• 分子量: 431.332
• InChiKey: ZQBBCISESJKWHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2-(2-bromopyridin-3-yl)-3-(1-phenylvinyl)-2,5-dihydro-1H-pyrrole 在 sodium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以77%的产率得到N-benzoyl-4-phenyl-2,3-dihydro-1H-pyrrolo[2,3-f ]quinoline
  参考文献：
  名称：

  Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles

  摘要：

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.

  DOI：

  10.1021/jo400246d
• 作为产物：
  描述：

  N-allyl-N-(1-(2-bromopyridin-3-yl)-3-phenylprop-2-yn-1-yl)-benzamide 在 Grubbs catalyst first generation 、 乙烯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以69%的产率得到N-benzoyl-2-(2-bromopyridin-3-yl)-3-(1-phenylvinyl)-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles

  摘要：

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.

  DOI：

  10.1021/jo400246d