Ethyl 2-(2-bromophenylamino)-2-diethoxyphosphorylacetate | 187034-16-8

• 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-(2-bromophenylamino)-2-diethoxyphosphorylacetate
• 英文别名: Ethyl 2-(2-bromoanilino)-2-diethoxyphosphorylacetate
• CAS: 187034-16-8
• 化学式: C₁₄H₂₁BrNO₅P
• 分子量: 394.202
• InChiKey: JQNZPZYUOWPIGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(2-bromophenylamino)-2-diethoxyphosphorylacetate 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-(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：

  ethyl 2-diazo-2-(diethoxyphosphoryl)acetate 、 2-溴苯胺 在 rhodium(II) acetate dimer 作用下， 以 甲苯 为溶剂， 以70%的产率得到Ethyl 2-(2-bromophenylamino)-2-diethoxyphosphorylacetate
  参考文献：
  名称：

  铑类胡萝卜素的NH插入反应。部分2.制备ñ -取代的氨基（磷酰基）乙酸酯（ñ -取代的磷酰基甘氨酸酯）

  摘要：

  乙酸铑（II）催化2-重氮-2-二乙氧基磷酰乙酸乙酯2与氨基甲酸酯，酰胺，脲或苯胺的反应，通过中间体的NH插入反应，可得到一系列N取代的2-氨基-2-二乙氧基磷酰乙酸3–18。铑类胡萝卜素。

  DOI：

  10.1039/p19960002885

文献信息

• N–H insertion reactions of rhodium carbenoids. Part 2. Preparation of N-substituted amino(phosphoryl)acetates (N-substituted phosphorylglycine esters)
  作者：Leigh Ferris、David Haigh、Christopher J. Moody

  DOI：10.1039/p19960002885

  日期：——

  Rhodium(II) acetate-catalysed reaction of ethyl 2-diazo-2-diethoxyphosphorylacetate 2 with carbamates, amides, ureas or anilines gives a range of N-substituted 2-amino-2-diethoxyphosphorylacetates 3–18 by N-H insertion reaction of the intermediate rhodium carbenoid.

  乙酸铑（II）催化2-重氮-2-二乙氧基磷酰乙酸乙酯2与氨基甲酸酯，酰胺，脲或苯胺的反应，通过中间体的NH插入反应，可得到一系列N取代的2-氨基-2-二乙氧基磷酰乙酸3–18。铑类胡萝卜素。
• 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.