3-(4-tert-butylphenylamino)-4-(4-nitrophenylamino)cyclobut-3-ene-1,2-dione | 1233032-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-tert-butylphenylamino)-4-(4-nitrophenylamino)cyclobut-3-ene-1,2-dione
• 英文别名: 3-(4-Tert-butylanilino)-4-(4-nitroanilino)cyclobut-3-ene-1,2-dione
• CAS: 1233032-34-2
• 化学式: C₂₀H₁₉N₃O₄
• 分子量: 365.389
• InChiKey: WSDCFHOBLWQRAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(4-nitrophenylamino)-4-ethoxycyclobut-3-ene-1,2-dione 、 4-叔丁基苯胺 在 zinc trifluoromethanesulfonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 以93%的产率得到3-(4-tert-butylphenylamino)-4-(4-nitrophenylamino)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  N,N′-Diarylsquaramides: General, High-Yielding Synthesis and Applications in Colorimetric Anion Sensing

  摘要：

  Zinc trilluoromethanesullonate promotes efficient condensations of anilines with squarate esters, providing access to symmetrical and unsymmetrical squaramides in high yields from readily available starting materials. Efficient access to electron-deficient diaryl squaramides has enabled a systematic investigation of the colorimetric anion-sensing behavior of a p-nitro-substituted squaramide. Its behavior differs in dramatic and unexpected ways from that of structurally similar p-nitroaniline-based ureas, an effect that highlights the remarkable differences in acidity between the squaramide and urea functional groups. Computational studies illustrating the enhanced hydrogen bond donor ability and acidity of squaramides in comparison to ureas are presented.

  DOI：

  10.1021/jo100104g

文献信息

• <i>N</i>,<i>N′</i>-Diarylsquaramides: General, High-Yielding Synthesis and Applications in Colorimetric Anion Sensing
  作者：Ali Rostami、Alexis Colin、Xiao Yu Li、Michael G. Chudzinski、Alan J. Lough、Mark S. Taylor

  DOI：10.1021/jo100104g

  日期：2010.6.18

  Zinc trilluoromethanesullonate promotes efficient condensations of anilines with squarate esters, providing access to symmetrical and unsymmetrical squaramides in high yields from readily available starting materials. Efficient access to electron-deficient diaryl squaramides has enabled a systematic investigation of the colorimetric anion-sensing behavior of a p-nitro-substituted squaramide. Its behavior differs in dramatic and unexpected ways from that of structurally similar p-nitroaniline-based ureas, an effect that highlights the remarkable differences in acidity between the squaramide and urea functional groups. Computational studies illustrating the enhanced hydrogen bond donor ability and acidity of squaramides in comparison to ureas are presented.