(Z)-2-(2-Bromo-phenylamino)-3-(2-iodo-5-nitro-phenyl)-acrylic acid ethyl ester | 265308-32-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2-(2-Bromo-phenylamino)-3-(2-iodo-5-nitro-phenyl)-acrylic acid ethyl ester
• CAS: 265308-32-5
• 化学式: C₁₇H₁₄BrIN₂O₄
• 分子量: 517.118
• InChiKey: WJKIMEYUHPLPFN-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-(2-Bromo-phenylamino)-3-(2-iodo-5-nitro-phenyl)-acrylic acid ethyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以90%的产率得到1-(2-Bromo-phenyl)-5-nitro-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of N-aryl indole-2-carboxylates via an intramolecular palladium-catalysed annulation of didehydrophenylalanine derivatives

  摘要：

  Nitrogen substituted indole-2-carboxylates can be prepared via an intramolecular palladium-catalysed amination reaction of didehydrophenylalanine derivatives using PdCl2(dppf) and KOAc in DMF at 90 degrees C to form the indole nucleus. The specific formation of (Z)-isomers from Horner-Wadsworth-Emmons reaction of phosphonylglycinates and 2-iodobenzaldehydes was crucial to the success of the process, The product N-substituted indole-2-carboxylates were isolated in high yield. (C) 2000 Elsevier Science Ltd, Ail rights reserved.

  DOI：

  10.1016/s0040-4039(99)02344-8
• 作为产物：
  描述：

  2-溴苯胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 dirhodium tetraacetate 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 (Z)-2-(2-Bromo-phenylamino)-3-(2-iodo-5-nitro-phenyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of N-aryl indole-2-carboxylates via an intramolecular palladium-catalysed annulation of didehydrophenylalanine derivatives

  摘要：

  Nitrogen substituted indole-2-carboxylates can be prepared via an intramolecular palladium-catalysed amination reaction of didehydrophenylalanine derivatives using PdCl2(dppf) and KOAc in DMF at 90 degrees C to form the indole nucleus. The specific formation of (Z)-isomers from Horner-Wadsworth-Emmons reaction of phosphonylglycinates and 2-iodobenzaldehydes was crucial to the success of the process, The product N-substituted indole-2-carboxylates were isolated in high yield. (C) 2000 Elsevier Science Ltd, Ail rights reserved.

  DOI：

  10.1016/s0040-4039(99)02344-8