ethyl 1-benzyl-5-(1-ethoxyvinyl)-1H-imidazole-4-carboxylate | 958867-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-benzyl-5-(1-ethoxyvinyl)-1H-imidazole-4-carboxylate
• 英文别名: Ethyl 1-benzyl-5-(1-ethoxyethenyl)imidazole-4-carboxylate
• CAS: 958867-84-0
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: IOPQEGGANYTQIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-5-(1-ethoxyvinyl)-1H-imidazole-4-carboxylate 在 吡啶 、 三氯化铁 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 58.0h， 生成 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 、 三丁基(1-乙氧基乙烯)锡 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以97%的产率得到ethyl 1-benzyl-5-(1-ethoxyvinyl)-1H-imidazole-4-carboxylate
  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