Diethyl 3-(furan-2-yl)-5-oxo-1-(2-oxochromen-6-yl)pyrrolidine-2,2-dicarboxylate | 1384975-66-9

• 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: Diethyl 3-(furan-2-yl)-5-oxo-1-(2-oxochromen-6-yl)pyrrolidine-2,2-dicarboxylate
• CAS: 1384975-66-9
• 化学式: C₂₃H₂₁NO₈
• 分子量: 439.422
• InChiKey: CTOLJFIIPKGJPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Diethyl 3-(furan-2-yl)-5-oxo-1-(2-oxochromen-6-yl)pyrrolidine-2,2-dicarboxylate 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 potassium hydroxide 、 silver(l) oxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 1.5h， 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：

  溴代丙二酸二乙酯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 Diethyl 3-(furan-2-yl)-5-oxo-1-(2-oxochromen-6-yl)pyrrolidine-2,2-dicarboxylate
  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