(E)-ethyl 2-(2,4-dioxochroman-3-ylidene)-2-(methylamino)acetate | 1429128-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-ethyl 2-(2,4-dioxochroman-3-ylidene)-2-(methylamino)acetate
• 英文别名: ethyl (2E)-2-(2,4-dioxochromen-3-ylidene)-2-(methylamino)acetate
• CAS: 1429128-22-2
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: BYPSFBYTHUMIIJ-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 N-(2-ethoxy-2-oxoethylidene)methylamine N-oxide 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以45.946%的产率得到
  参考文献：
  名称：

  Self-Catalyzed Mannich-Type Reaction of Enolizable Cyclic 1,3-Dicarbonyls to Acyclic Nitrones: An Entry to Functionalized β-Enamino Diones

  摘要：

  A new method for the preparation of highly functionalized beta-enamino diones has been developed. The protocol involves an initial self-catalyzed Mannich-type reaction of enolizable cyclic 1,3-dicarbonyls to nitrones, followed by a spontaneous intramolecular reorganization of the resulting nonisolated hydroxylamine to enamino derivatives. These compounds retain the features of unnatural a-amino acids. The ease of preparation makes them attractive intermediates for the synthesis of peptidomimetics, polyheterocycles, and other multifunctional compounds. All experimental results have been efficiently rationalized by in silico studies at the M06-2X level of theory, and a valid mechanistic pathway has been proposed.

  DOI：

  10.1021/jo400331b

文献信息

• Self-Catalyzed Mannich-Type Reaction of Enolizable Cyclic 1,3-Dicarbonyls to Acyclic Nitrones: An Entry to Functionalized β-Enamino Diones
  作者：Massimiliano Cordaro、Francesco Risitano、Angela Scala、Antonio Rescifina、Ugo Chiacchio、Giovanni Grassi

  DOI：10.1021/jo400331b

  日期：2013.4.19

  A new method for the preparation of highly functionalized beta-enamino diones has been developed. The protocol involves an initial self-catalyzed Mannich-type reaction of enolizable cyclic 1,3-dicarbonyls to nitrones, followed by a spontaneous intramolecular reorganization of the resulting nonisolated hydroxylamine to enamino derivatives. These compounds retain the features of unnatural a-amino acids. The ease of preparation makes them attractive intermediates for the synthesis of peptidomimetics, polyheterocycles, and other multifunctional compounds. All experimental results have been efficiently rationalized by in silico studies at the M06-2X level of theory, and a valid mechanistic pathway has been proposed.