Ethyl 2-[diethoxy(oxido)phosphaniumyl]-2-[4-(2-ethoxy-2-oxoethyl)anilino]acetate | 265308-29-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 2-[diethoxy(oxido)phosphaniumyl]-2-[4-(2-ethoxy-2-oxoethyl)anilino]acetate
• 英文别名: ethyl 2-[diethoxy(oxido)phosphaniumyl]-2-[4-(2-ethoxy-2-oxoethyl)anilino]acetate
• CAS: 265308-29-0
• 化学式: C₁₈H₂₈NO₇P
• 分子量: 401.397
• InChiKey: QCWUMFPEIVDQDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[diethoxy(oxido)phosphaniumyl]-2-[4-(2-ethoxy-2-oxoethyl)anilino]acetate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-(4-Ethoxycarbonylmethyl-phenyl)-6-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：

  ethyl 2-diazo-2-(diethoxyphosphoryl)acetate 、 4-氨基苯乙酸乙酯 在 dirhodium tetraacetate 作用下， 以 甲苯 为溶剂， 以90%的产率得到Ethyl 2-[diethoxy(oxido)phosphaniumyl]-2-[4-(2-ethoxy-2-oxoethyl)anilino]acetate
  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

文献信息

• Synthesis of N-aryl indole-2-carboxylates via an intramolecular palladium-catalysed annulation of didehydrophenylalanine derivatives
  作者：Julien A Brown

  DOI：10.1016/s0040-4039(99)02344-8

  日期：2000.3

  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.