ethyl 2-(5-chloro-1H-indol-3-yl)-2-((4-fluorophenyl)amino)acetate | 1609550-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 2-(5-chloro-1H-indol-3-yl)-2-((4-fluorophenyl)amino)acetate
• 英文别名: ethyl 2-(5-chloro-1H-indol-3-yl)-2-(4-fluoroanilino)acetate
• CAS: 1609550-05-1
• 化学式: C₁₈H₁₆ClFN₂O₂
• 分子量: 346.789
• InChiKey: RZLBEGRPWPCBBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-nitro-2-diazoacetate 、 5-氯吲哚 、 4-氟苯胺 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-(2-(difluoroboryl)phenyl)urea 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以58%的产率得到ethyl 2-(5-chloro-1H-indol-3-yl)-2-((4-fluorophenyl)amino)acetate
  参考文献：
  名称：

  Urea-Catalyzed N–H Insertion–Arylation Reactions of Nitrodiazoesters

  摘要：

  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.

  DOI：

  10.1021/jo500698q

文献信息

• 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.