2-(2-oxo-2H-chromen-6-yl-amino)malonic acid diethyl ester | 1384975-61-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-(2-oxo-2H-chromen-6-yl-amino)malonic acid diethyl ester
• 英文别名: Diethyl 2-[(2-oxochromen-6-yl)amino]propanedioate
• CAS: 1384975-61-4
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: SSZZPTXHXKUFGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-2H-chromen-6-yl-amino)malonic acid diethyl ester 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 苯 为溶剂， 生成
  参考文献：
  名称：

  N-Aryl Modification in γ-Lactam: Design and Synthesis of Novel Monocyclic γ-Lactam Derivatives as Inhibitor for Bacterial Propagation

  摘要：

  In search of novel gamma-lactam antibacterial agents as non-beta-lactam mimics of some c-lactam antibiotics, N-aryl modification in the gamma-lactam ring has been made to synthesize compounds 4-8 in two to six steps. Compound 4 was synthesized using the intermolecular Michael addition of diethyl N-(6-coumarinyl)-2-aminomalonate and 3-aryl/(2-heteroaryl) acryloyl chloride followed by intramolecular amidification. Hydrolysis and stereoselective decarboxylation of 4 resulted in the formation of trans-gamma-lactam carboxylic acids (5), which on side chain homologation followed by saponification of the intermediate gamma-lactam monoester (7) afforded gamma-lactam carboxylic derivatives 8. Moderate to good bacterial growth inhibition was observed for some of the synthesized compounds against E. coli and S. aureus.

  DOI：

  10.1080/00397911.2011.574807
• 作为产物：
  描述：

  2H-1-苯并吡喃-2-酮,6-氨基- 、 溴代丙二酸二乙酯 反应 3.0h， 以70%的产率得到2-(2-oxo-2H-chromen-6-yl-amino)malonic acid diethyl ester
  参考文献：
  名称：

  N-Aryl Modification in γ-Lactam: Design and Synthesis of Novel Monocyclic γ-Lactam Derivatives as Inhibitor for Bacterial Propagation

  摘要：

  In search of novel gamma-lactam antibacterial agents as non-beta-lactam mimics of some c-lactam antibiotics, N-aryl modification in the gamma-lactam ring has been made to synthesize compounds 4-8 in two to six steps. Compound 4 was synthesized using the intermolecular Michael addition of diethyl N-(6-coumarinyl)-2-aminomalonate and 3-aryl/(2-heteroaryl) acryloyl chloride followed by intramolecular amidification. Hydrolysis and stereoselective decarboxylation of 4 resulted in the formation of trans-gamma-lactam carboxylic acids (5), which on side chain homologation followed by saponification of the intermediate gamma-lactam monoester (7) afforded gamma-lactam carboxylic derivatives 8. Moderate to good bacterial growth inhibition was observed for some of the synthesized compounds against E. coli and S. aureus.

  DOI：

  10.1080/00397911.2011.574807