4-(N,N-diphenylamino)-5-hydroxy-3H-furan-2-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(N,N-diphenylamino)-5-hydroxy-3H-furan-2-one
• 英文别名: 5-hydroxy-4-(N-phenylanilino)-3H-furan-2-one
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: BQUGXHXWDYPCBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  马来酸酐 、 二苯胺 以 甲苯 为溶剂， 反应 0.5h， 以65%的产率得到4-(N,N-diphenylamino)-5-hydroxy-3H-furan-2-one
  参考文献：
  名称：

  Tandem Michael addition of amines to maleic anhydride and 1,3-prototropic shift: experimental and theoretical results

  摘要：

  Amines, namely diethylamine, diphenylamine, benzylamine, and pyrrolidine react with maleic anhydride to form Michael adducts. The Michael adducts formed with the first three amines undergo tandem 1,3-prototropic shift to give the final products. Computational calculations at the DFT (B3LYP/6-31+G*) level reveal that a reactant-complex formed between the initially formed Michael adduct and the respective amine plays a crucial role in the 1,3-prototropic shift. In the reaction of pyrrolidine with maleic anhydride, Michael addition is not followed by 1,3-prototropic shift. The theoretical studies of the latter reaction show that a reactant-complex is not formed in this case. Dimethyl maleate and dimethyl fumarate react with pyrrolidine to give the same Michael addition product. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.003

文献信息

• Tandem Michael addition of amines to maleic anhydride and 1,3-prototropic shift: experimental and theoretical results
  作者：Asha Gurjar、Pragya Sinha、Raj K. Bansal

  DOI：10.1016/j.tet.2014.06.003

  日期：2014.8

  Amines, namely diethylamine, diphenylamine, benzylamine, and pyrrolidine react with maleic anhydride to form Michael adducts. The Michael adducts formed with the first three amines undergo tandem 1,3-prototropic shift to give the final products. Computational calculations at the DFT (B3LYP/6-31+G*) level reveal that a reactant-complex formed between the initially formed Michael adduct and the respective amine plays a crucial role in the 1,3-prototropic shift. In the reaction of pyrrolidine with maleic anhydride, Michael addition is not followed by 1,3-prototropic shift. The theoretical studies of the latter reaction show that a reactant-complex is not formed in this case. Dimethyl maleate and dimethyl fumarate react with pyrrolidine to give the same Michael addition product. (C) 2014 Elsevier Ltd. All rights reserved.