Methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate | 150097-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate
• 英文别名: methyl 4-(pentafluoroethyl)-2-propyl-1H-imidazole-5-carboxylate；Methyl 5-(pentafluoroethyl)-2-propyl-1H-imidazole-4-carboxylate；methyl 5-(1,1,2,2,2-pentafluoroethyl)-2-propyl-1H-imidazole-4-carboxylate
• CAS: 150097-92-0
• 化学式: C₁₀H₁₁F₅N₂O₂
• 分子量: 286.202
• InChiKey: BCIVUDCPEOVGBW-UHFFFAOYSA-N

物化性质

• 沸点：
  354.5±42.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 5-Pentafluoroethyl-2-propyl-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid methyl ester
  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-戊炔酸,4,4,5,5,5-五氟-,甲基酯 在 sodium azide 、 碘苯二乙酸 、 potassium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.17h， 生成 Methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate
  参考文献：
  名称：

  通过无金属级联迈克尔加成/叠氮化/环化工艺有效合成氟代烷基化的咪唑

  摘要：

  据报道，通过迈克尔加成，叠氮化和环胺化反应，可以由伯胺与α-氢和氟代烷基炔烃有效地级联一锅合成氟代烷基化的咪唑。探索了底物的范围。阐明了该机制，并演示了该应用程序。

  DOI：

  10.1002/ejoc.201801310

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').
• Efficient Synthesis of Fluoroalkylated Imidazoles via a Metal-Free Cascade Michael Addition/Azidation/Cycloamination Process
  作者：Jun Wu、Hui Zhang、Xiao Ding、Xuefei Tan、Hong C. Shen、Jie Chen、Weimin He、Hongmei Deng、Liping Song、Weiguo Cao

  DOI：10.1002/ejoc.201801310

  日期：2018.12.19

  An efficient cascade one‐pot synthesis of fluoroalkylated imidazoles from primary amines with α‐hydrogen and fluoroalkylated alkynes via Michael addition, azidation and cycloamination was reported. Substrates scope was explored. The mechanism was elucidated and the application was also demonstrated.

  据报道，通过迈克尔加成，叠氮化和环胺化反应，可以由伯胺与α-氢和氟代烷基炔烃有效地级联一锅合成氟代烷基化的咪唑。探索了底物的范围。阐明了该机制，并演示了该应用程序。