N-benzoyl-2-(2-bromophenyl)-3-(1-(4-methoxyphenyl)vinyl)-1,2,5,6-tetrahydropyridine | 1428883-89-9

• 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: N-benzoyl-2-(2-bromophenyl)-3-(1-(4-methoxyphenyl)vinyl)-1,2,5,6-tetrahydropyridine
• CAS: 1428883-89-9
• 化学式: C₂₇H₂₄BrNO₂
• 分子量: 474.397
• InChiKey: SFVCTCIEFQXOBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2-(2-bromophenyl)-3-(1-(4-methoxyphenyl)vinyl)-1,2,5,6-tetrahydropyridine 在 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以80%的产率得到(4aR*,5aR*,9bS*)-N-benzoyl-5a-(4-methoxyphenyl)-2,5,5a,9b-tetrahydro-1Hcyclopropa[2,3]indeno[1,2-b]pyridine
  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：

  苯甲酰氯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 乙烯 、 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 10.0h， 生成 N-benzoyl-2-(2-bromophenyl)-3-(1-(4-methoxyphenyl)vinyl)-1,2,5,6-tetrahydropyridine
  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