Methyl 2-propyl-4(5)-iodoimidazole-5(4)-carboxylate | 150097-91-9

• 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 2-propyl-4(5)-iodoimidazole-5(4)-carboxylate
• 英文别名: methyl 5-iodo-2-propyl-1H-imidazole-4-carboxylate
• CAS: 150097-91-9
• 化学式: C₈H₁₁IN₂O₂
• 分子量: 294.092
• InChiKey: QUHZLQPTADOKDE-UHFFFAOYSA-N

物化性质

• 沸点：
  404.6±25.0 °C(Predicted)
• 密度：
  1.727±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-propyl-4(5)-iodoimidazole-5(4)-carboxylate 在 铜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 Methyl 4-(pentafluoroethyl)-2-propyl-1-<<2'-biphenyl-4-yl>methyl>imidazole-5-carboxylate
  参考文献：
  名称：

  Practical synthesis and regioselective alkylation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate to give DuP 532, a potent angiotensin II antagonist

  摘要：

  DuP 532 (2), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes. One route, which is more practical for large-scale synthesis, required the preparation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (9). This imidazole was synthesized in five steps from commercially available 11 in 32% overall yield. Alternate perfluoroalkylation methods of the iodoimidazole precursor 14 are presented. Imidazole 9 is remarkably stable to basic conditions and is alkylated by 2-[N-(triphenylmethyl)tetrazol-5-yl]-4'-(bromomethyl)-1,1'-biphenyl (8), giving only the desired regioisomer. A comparison of the alkylation of the trisubstituted precursors and analogues to 9 with 8 indicate that even under mildly basic conditions (K2CO3/DMF), the mechanism is S(E)2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole (11) which alkylates as a neutral species (S(E)2').

  DOI：

  10.1021/jo00069a029
• 作为产物：
  描述：

  2-Propyl-4(5)-iodoimidazole-5(4)-carboxaldehyde oxime 在 硫酸 、 乙酸酐 作用下， 反应 68.0h， 生成 Methyl 2-propyl-4(5)-iodoimidazole-5(4)-carboxylate
  参考文献：
  名称：

  Practical synthesis and regioselective alkylation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate to give DuP 532, a potent angiotensin II antagonist

  摘要：

  DuP 532 (2), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes. One route, which is more practical for large-scale synthesis, required the preparation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (9). This imidazole was synthesized in five steps from commercially available 11 in 32% overall yield. Alternate perfluoroalkylation methods of the iodoimidazole precursor 14 are presented. Imidazole 9 is remarkably stable to basic conditions and is alkylated by 2-[N-(triphenylmethyl)tetrazol-5-yl]-4'-(bromomethyl)-1,1'-biphenyl (8), giving only the desired regioisomer. A comparison of the alkylation of the trisubstituted precursors and analogues to 9 with 8 indicate that even under mildly basic conditions (K2CO3/DMF), the mechanism is S(E)2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole (11) which alkylates as a neutral species (S(E)2').

  DOI：

  10.1021/jo00069a029

文献信息

• Practical synthesis and regioselective alkylation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate to give DuP 532, a potent angiotensin II antagonist
  作者：Michael E. Pierce、David J. Carini、George F. Huhn、Gregory J. Wells、John F. Arnett

  DOI：10.1021/jo00069a029

  日期：1993.8

  DuP 532 (2), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes. One route, which is more practical for large-scale synthesis, required the preparation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (9). This imidazole was synthesized in five steps from commercially available 11 in 32% overall yield. Alternate perfluoroalkylation methods of the iodoimidazole precursor 14 are presented. Imidazole 9 is remarkably stable to basic conditions and is alkylated by 2-[N-(triphenylmethyl)tetrazol-5-yl]-4'-(bromomethyl)-1,1'-biphenyl (8), giving only the desired regioisomer. A comparison of the alkylation of the trisubstituted precursors and analogues to 9 with 8 indicate that even under mildly basic conditions (K2CO3/DMF), the mechanism is S(E)2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole (11) which alkylates as a neutral species (S(E)2').