ethyl 2-(4-aminophenyl)-2-(phenylamino)acetate | 1378021-00-1

• 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-(4-aminophenyl)-2-(phenylamino)acetate
• 英文别名: ethyl 2-(4-aminophenyl)-2-anilinoacetate
• CAS: 1378021-00-1
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: RCJNNIZZBNJGNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-aminophenyl)-2-(phenylamino)acetate 在 silver trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以94%的产率得到2,2-Bis-(4-amino-phenyl)-essigsaeure-aethylester
  参考文献：
  名称：

  路易斯酸催化苯胺和乙醛酸盐之间的选择性傅克反应或环化反应

  摘要：

  开发了苯胺和乙醛酸盐之间的路易斯酸催化选择性反应，用于合成二芳基甲烷或氧代咪唑烷。在AgOTf的催化下，以中等至良好的收率获得了一系列基于苯胺的二芳基甲烷，包括伯苯胺、仲苯胺和叔苯胺。此外，在Cu(OAc) 2 ·H 2 O的催化下，进行了立体选择性氧代咪唑烷的制备。

  DOI：

  10.1021/acs.orglett.2c01115
• 作为产物：
  描述：

  乙醛酸乙酯 、 苯胺 在 magnesium chloride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 10.0h， 以44%的产率得到ethyl 2-(4-aminophenyl)-2-(phenylamino)acetate
  参考文献：
  名称：

  路易斯酸催化苯胺和乙醛酸盐之间的选择性傅克反应或环化反应

  摘要：

  开发了苯胺和乙醛酸盐之间的路易斯酸催化选择性反应，用于合成二芳基甲烷或氧代咪唑烷。在AgOTf的催化下，以中等至良好的收率获得了一系列基于苯胺的二芳基甲烷，包括伯苯胺、仲苯胺和叔苯胺。此外，在Cu(OAc) 2 ·H 2 O的催化下，进行了立体选择性氧代咪唑烷的制备。

  DOI：

  10.1021/acs.orglett.2c01115

文献信息

• Internal Lewis acid assisted ureas: tunable hydrogen bond donor catalysts
  作者：David M. Nickerson、Veronica V. Angeles、Tyler J. Auvil、Sonia S. So、Anita E. Mattson

  DOI：10.1039/c2cc37073e

  日期：——

  The strategic incorporation of internal Lewis acids onto urea scaffolds gives rise to a family of tunable hydrogen bond donor catalysts. The nature of the Lewis acid and associated ligands affects the urea polarization, acidity, and activity in reactions of nitrocyclopropane carboxylates and nitrodiazoesters.

  内部路易斯酸在尿素支架上的战略性引入产生了一系列可调氢键供体催化剂。路易斯酸和相关配体的性质会影响尿素的极性，酸度以及硝基环丙烷羧酸酯和硝基二偶氮酯的反应活性。
• A catalyst-free N–H insertion/Mannich-type reaction cascade of α-nitrodiazoesters
  作者：Ting Yang、Hao Zhuang、Xichen Lin、Jia-Ning Xiang、John D. Elliott、Lianghui Liu、Feng Ren

  DOI：10.1016/j.tetlet.2013.05.131

  日期：2013.8

  A catalyst-free N-H insertion/Mannich-type reaction cascade of alpha-nitrodiazoesters with anilines has been developed to afford a variety of alpha-amino-alpha-aryl esters in 60-83% yields and under mild reaction conditions (23 or 40 degrees C). (C) 2013 Elsevier Ltd. All rights reserved.
• Urea Activation of α-Nitrodiazoesters: An Organocatalytic Approach to N–H Insertion Reactions
  作者：Sonia S. So、Anita E. Mattson

  DOI：10.1021/ja3031054

  日期：2012.5.30

  The combination of a urea catalyst and an a-nitro-a-diazo ester gives rise to a reactive species able to undergo insertion into the N-H bonds of anilines. This new strategy to achieve N-H insertion reactivity is in contrast to typical metal-catalyzed conditions for the generation of carbenoids from alpha-diazocarbonyl compounds. This report includes the extension of the insertion reaction to a three-component coupling for the construction of alpha-amino-alpha-aryl esters in high yield.
• Urea-Catalyzed N–H Insertion–Arylation Reactions of Nitrodiazoesters
  作者：Sonia S. So、Shameema Oottikkal、Jovica D. Badjić、Christopher M. Hadad、Anita E. Mattson

  DOI：10.1021/jo500698q

  日期：2014.6.6

  The power of hydrogen-bond donor catalysis has been harnessed to elicit and control carbene-like reactivity from nitrodiazoesters. Specifically, select ureas have been identified as effective catalysts for N-H insertion and multicomponent coupling reactions of nitrodiazoesters, anilines, and aromatic nucleophiles, thereby preparing a variety of alpha-aryl glycines in high yield. Experimental and computational studies designed to probe the plausible reaction pathways suggest that difluoroboronate ureas are particularly well-suited to catalyze reactions of nitrodiazoesters with a range of anilines through a polar reaction pathway Urea-facilitated loss of nitrite followed by addition of a nucleophile conceivably generates the observed aryl glycine products.