2-Propyl-4(5)-cyano-5(4)-iodoimidazole | 134380-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Propyl-4(5)-cyano-5(4)-iodoimidazole
• 英文别名: 5-Iodo-2-propyl-1H-imidazole-4-carbonitrile
• CAS: 134380-65-7
• 化学式: C₇H₈IN₃
• 分子量: 261.065
• InChiKey: KAAOPNAXJOHPFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-Propyl-4(5)-cyano-5(4)-iodoimidazole 在 盐酸 、 sodium hydroxide 、 硫酸 、 铜 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 5-(1,1,2,2,2-五氟乙基)-2-丙基-3-[[4-[2-(2H-四唑-5-基)苯基]苯基]甲基]咪唑-4-羧酸
  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-n-Propyl-4-hydroxymethylimidazole 在 吡啶 、 manganese(IV) oxide 、 sodium periodate 、 硫酸 、 盐酸羟胺 、 碘 、 乙酸酐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 2-Propyl-4(5)-cyano-5(4)-iodoimidazole
  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