methyl-4-(1-benzyl-4-ethoxycarbonyl-1H-imidazol-5-yl)-4-ethoxy-2-oxobut-3-enoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl-4-(1-benzyl-4-ethoxycarbonyl-1H-imidazol-5-yl)-4-ethoxy-2-oxobut-3-enoate
• 英文别名: ethyl 1-benzyl-5-[(Z)-1-ethoxy-4-methoxy-3,4-dioxobut-1-enyl]imidazole-4-carboxylate
• 化学式: C₂₀H₂₂N₂O₆
• 分子量: 386.404
• InChiKey: OBCSLPLZDHLDMA-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  96.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl-4-(1-benzyl-4-ethoxycarbonyl-1H-imidazol-5-yl)-4-ethoxy-2-oxobut-3-enoate 在 三氯化铁 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以78%的产率得到methyl-4-(1-benzyl-4-ethoxycarbonyl-1H-imidazol-5-yl)-2-hydroxy-4-oxobut-2-enoate
  参考文献：
  名称：

  A Novel Strategy to Assemble the β-Diketo Acid Pharmacophore of HIV Integrase Inhibitors on Purine Nucleobase Scaffolds

  摘要：

  Claisen condensation, the key step in constructing the pharmacophore of aryl beta-diketo acids (DKA) as integrase inhibitors, fails in certain cases of highly electron-deficient heterocycles such as purines. A general synthetic strategy to assemble the DKA motif on the purine scaffold has been accomplished. The synthetic sequence entails a palladiumcatalyzed cross-coupling, a C-acylation.involving a tandem addition/elimination reaction, and a novel ferric ion-catalyzed selective hydrolysis of an enolic ether in the presence of a carboxylic acid ester.

  DOI：

  10.1021/jo701336r
• 作为产物：
  描述：

  ethyl-5-iodo-1-benzylimidazole-4-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 methyl-4-(1-benzyl-4-ethoxycarbonyl-1H-imidazol-5-yl)-4-ethoxy-2-oxobut-3-enoate
  参考文献：
  名称：

  A Novel Strategy to Assemble the β-Diketo Acid Pharmacophore of HIV Integrase Inhibitors on Purine Nucleobase Scaffolds

  摘要：

  Claisen condensation, the key step in constructing the pharmacophore of aryl beta-diketo acids (DKA) as integrase inhibitors, fails in certain cases of highly electron-deficient heterocycles such as purines. A general synthetic strategy to assemble the DKA motif on the purine scaffold has been accomplished. The synthetic sequence entails a palladiumcatalyzed cross-coupling, a C-acylation.involving a tandem addition/elimination reaction, and a novel ferric ion-catalyzed selective hydrolysis of an enolic ether in the presence of a carboxylic acid ester.

  DOI：

  10.1021/jo701336r