1-(2-(4-bromophenyl)-3-(4-methoxyphenyl)-1,2-dihydrobenzo[b][1,6]naphthyridin-1-yl)propan-2-one | 1430118-27-6

• 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: 1-(2-(4-bromophenyl)-3-(4-methoxyphenyl)-1,2-dihydrobenzo[b][1,6]naphthyridin-1-yl)propan-2-one
• 英文别名: 1-[2-(4-bromophenyl)-3-(4-methoxyphenyl)-1H-benzo[b][1,6]naphthyridin-1-yl]propan-2-one
• CAS: 1430118-27-6
• 化学式: C₂₈H₂₃BrN₂O₂
• 分子量: 499.407
• InChiKey: VMVPCGRIAYQDLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-(4-bromophenyl)-3-(4-methoxyphenyl)-1,2-dihydrobenzo[b][1,6]naphthyridin-1-yl)propan-2-one 、 4-甲苯硼酸 在 1-(2-吡啶基)苯并三唑 、 palladium diacetate 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以72%的产率得到1-(3-(4-methoxyphenyl)-2-(4'-methyl-[1,1'-biphenyl]-4-yl)-1,2-dihydrobenzo[b][1,6] naphthyridin-1-yl)propan-2-one
  参考文献：
  名称：

  Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction

  摘要：

  An efficient approach for the silver-catalyzed regioselective tandem synthesis of highly functionalized 1,2-dihydorbenzo[1,6]naphthyridines 6a-z and 7a-e by the reaction of ortho-alkynylaldehydes 3a-n with amines 4a-d and ketones 5a-c/active methylene compounds 5d-g, under mild reaction conditions, is described. The scope of the developed chemistry was successfully extended for the direct synthesis of 1,2-dihydorbenzo[4,5]thieno[2,3-c]pyridines 8a-e, which is known as the sulfur analogue of beta-carbolines. Naphthyridines 6a-z and thienopyridines 8a-e were obtained via dual activation concept using L-proline as organocatalyst; however, naphthyridines 7a-e were synthesized without using organocatalyst. The reaction shows selective N-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-digcyclized products. Reactivity behavior of electron-deficient and electron-rich ortho-alkynylaldehydes in the synthesis of naphthyridines and thienopyridine by three-component reaction is supported by the control experiment.

  DOI：

  10.1021/jo400400c
• 作为产物：
  描述：

  4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 silver nitrate 、 三乙胺 、 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 1-(2-(4-bromophenyl)-3-(4-methoxyphenyl)-1,2-dihydrobenzo[b][1,6]naphthyridin-1-yl)propan-2-one
  参考文献：
  名称：

  Silver-Catalyzed Tandem Synthesis of Naphthyridines and Thienopyridines via Three-Component Reaction

  摘要：

  An efficient approach for the silver-catalyzed regioselective tandem synthesis of highly functionalized 1,2-dihydorbenzo[1,6]naphthyridines 6a-z and 7a-e by the reaction of ortho-alkynylaldehydes 3a-n with amines 4a-d and ketones 5a-c/active methylene compounds 5d-g, under mild reaction conditions, is described. The scope of the developed chemistry was successfully extended for the direct synthesis of 1,2-dihydorbenzo[4,5]thieno[2,3-c]pyridines 8a-e, which is known as the sulfur analogue of beta-carbolines. Naphthyridines 6a-z and thienopyridines 8a-e were obtained via dual activation concept using L-proline as organocatalyst; however, naphthyridines 7a-e were synthesized without using organocatalyst. The reaction shows selective N-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-digcyclized products. Reactivity behavior of electron-deficient and electron-rich ortho-alkynylaldehydes in the synthesis of naphthyridines and thienopyridine by three-component reaction is supported by the control experiment.

  DOI：

  10.1021/jo400400c