2-Propyl-4(5)-(hydroxymethyl)-5(4)-iodoimidazole | 134051-69-7

• 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)-(hydroxymethyl)-5(4)-iodoimidazole
• 英文别名: 5-hydroxymethyl-4-iodo-2-n-propylimidazole；(4-iodo-2-propyl-1H-imidazol-5-yl)methanol
• CAS: 134051-69-7
• 化学式: C₇H₁₁IN₂O
• 分子量: 266.082
• InChiKey: FFDQDZXYBCHORZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Propyl-4(5)-(hydroxymethyl)-5(4)-iodoimidazole 在 吡啶 、 manganese(IV) oxide 、 硫酸 、 盐酸羟胺 、 乙酸酐 、 铜 作用下， 以 二氯甲烷 为溶剂， 反应 123.0h， 生成 Methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-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
• 作为产物：
  描述：

  2-n-Propyl-4-hydroxymethylimidazole 在 sodium periodate 、 硫酸 、 碘 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以77%的产率得到2-Propyl-4(5)-(hydroxymethyl)-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

文献信息

• Fused aryl substituted imidazole angiotensin II receptor inhibitors
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05254546A1

  公开（公告）日：1993-10-19

  Substituted imidazoles such as ##STR1## which are useful as angiotensin II receptor inhibitors. These compounds have activity in treating hypertension and congestive heart failure.

  取代咪唑类化合物，如##STR1##，可用作抑制血管紧张素II受体的药物。这些化合物具有治疗高血压和充血性心力衰竭的活性。
• Angiotensin II receptor blocking imidazoles
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05354867A1

  公开（公告）日：1994-10-11

  Substituted imidazoles such as ##STR1## are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.

  替代咪唑，例如##STR1##，可用作血管紧张素II受体拮抗剂。这些化合物对治疗高血压和充血性心力衰竭具有活性。
• FUSED-RING ARYL SUBSTITUTED IMIDAZOLES
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0479892A1

  公开（公告）日：1992-04-15
• SUBSTITUTED IMIDAZOLES
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0479903A1

  公开（公告）日：1992-04-15
• SUBSTITUTED IMIDAZOLES USEFUL AS ANGIOTENSIN II BLOCKERS
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0479903B1

  公开（公告）日：1996-02-21