ethyl 2-((4-fluorophenyl)amino)-2-(4-(methylamino)phenyl)acetate | 1609550-02-8

• 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-((4-fluorophenyl)amino)-2-(4-(methylamino)phenyl)acetate
• 英文别名: Ethyl 2-(4-fluoroanilino)-2-[4-(methylamino)phenyl]acetate；ethyl 2-(4-fluoroanilino)-2-[4-(methylamino)phenyl]acetate
• CAS: 1609550-02-8
• 化学式: C₁₇H₁₉FN₂O₂
• 分子量: 302.348
• InChiKey: LKNXJDBPKUKQKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯甲基苯胺 、 ethyl 2-((4-fluorophenyl)amino)-2-(4-(methylamino)phenyl)acetate 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以76%的产率得到ethyl 2-(4-(benzylamino)phenyl)-2-(4-(methylamino)phenyl)acetate
  参考文献：
  名称：

  Synthesis of Unsymmetrical α,α-Diarylacetates

  摘要：

  Ethyl bromofluoroacetate has been developed as a precursor for the convenient synthesis of unsymmetrical alpha,alpha-diarylacetates featuring indoles, anilines, and other electron-rich aromatics. In conjunction with a mild Lewis acid catalyzed C-N -> C-C exchange, intermediate arylglycines can be synthesized and transformed into alpha,alpha a-diarylacetates in a one-pot protocol, resulting in a net diarylation reaction exhibiting a wide scope. In the context of diarylacetates, the synthetic equivalence of the fluorinated reagent with a-nitro-a-diazo carbonyls was established.

  DOI：

  10.1021/acs.joc.5b02383
• 作为产物：
  描述：

  溴氟乙酸乙酯 、 N-甲基苯胺 、 4-氟苯胺 在 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以80%的产率得到ethyl 2-((4-fluorophenyl)amino)-2-(4-(methylamino)phenyl)acetate
  参考文献：
  名称：

  Synthesis of Unsymmetrical α,α-Diarylacetates

  摘要：

  Ethyl bromofluoroacetate has been developed as a precursor for the convenient synthesis of unsymmetrical alpha,alpha-diarylacetates featuring indoles, anilines, and other electron-rich aromatics. In conjunction with a mild Lewis acid catalyzed C-N -> C-C exchange, intermediate arylglycines can be synthesized and transformed into alpha,alpha a-diarylacetates in a one-pot protocol, resulting in a net diarylation reaction exhibiting a wide scope. In the context of diarylacetates, the synthetic equivalence of the fluorinated reagent with a-nitro-a-diazo carbonyls was established.

  DOI：

  10.1021/acs.joc.5b02383

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.
• Synthesis of Unsymmetrical α,α-Diarylacetates
  作者：Santosh D. Jadhav、Anand Singh

  DOI：10.1021/acs.joc.5b02383

  日期：2016.1.15

  Ethyl bromofluoroacetate has been developed as a precursor for the convenient synthesis of unsymmetrical alpha,alpha-diarylacetates featuring indoles, anilines, and other electron-rich aromatics. In conjunction with a mild Lewis acid catalyzed C-N -> C-C exchange, intermediate arylglycines can be synthesized and transformed into alpha,alpha a-diarylacetates in a one-pot protocol, resulting in a net diarylation reaction exhibiting a wide scope. In the context of diarylacetates, the synthetic equivalence of the fluorinated reagent with a-nitro-a-diazo carbonyls was established.