ethyl 4-trifluoromethylpyrimido[1,2-a]benzimidazole-3-carboxylate | 1240485-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: ethyl 4-trifluoromethylpyrimido[1,2-a]benzimidazole-3-carboxylate
• 英文别名: Ethyl 4-trifluoromethylpyrimido[1,2-a]benz-imidazole-3-carboxylate；ethyl 4-(trifluoromethyl)pyrimido[1,2-a]benzimidazole-3-carboxylate
• CAS: 1240485-93-1
• 化学式: C₁₄H₁₀F₃N₃O₂
• 分子量: 309.248
• InChiKey: DFQIBFXCFQGTBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基苯并咪唑 、 乙氧基-2-亚甲基三氟乙酰乙酸乙酯 以 四氢呋喃 为溶剂， 反应 2.0h， 以56%的产率得到ethyl 4-hydroxy-4-trifluoromethyl-1,4-dihydropyrimido[1,2-a]benzimidazole-3-carboxylate
  参考文献：
  名称：

  Regiodirected synthesis of polyfluoro-alkylated pyrimido[1,2-a]benzimidazoles

  摘要：

  Conditions have been found for the regiodirected cyclization of 2-aminobenzimidazoles using ethyl 3-oxo-3-polyfluoroalkyl-2-ethoxymethylidenepropionates at the ethoxymethylidenefluoroacyl fragment to give ethyl pyrimidobenzimidazole-3-carboxylates.

  DOI：

  10.1007/s10593-012-1000-8

文献信息

• Synthesis of pyrimido[1,2-a]benzimidazoles from ethyl 2-ethoxymethylidene-3-oxo-3-(polyfluoroalkyl)propionates
  作者：M. V. Goryaeva、Ya. V. Burgart、V. I. Saloutin

  DOI：10.1134/s1070428010030231

  日期：2010.3

  Cyclization of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with benzimidazol-2-amine in boiling 1,4-dioxane followed two concurrent pathways with participation of fluoroacyl and ethoxycarbonyl fragments and formation of, respectively, ethyl 4-hydroxy-4-polyfluoroalkyl-1,4-dihydropyrimido-[1,2-a]benzimidazole-3-carboxylates and 3-polyfluoroacylpyrimido[1,2-a]benzimidazol-4-ols. Dihydropyrimido[1,2-a]benzimidazole derivatives undergo dehydration to give ethyl 4-(polyfluoroalkyl)pyrimido[1,2-a]benzimidazole-3-carboxylates, whereas the hydroxy group in 3-polyfluoroacylpyrimido[1,2-a]benzimidazol-4-ols is capable of being replaced by the amino group of the second benzimidazole molecule with formation of 4-(1H-benzimidazol-2-ylamino)-3-polyfluoroacylpyrimido[1,2-a]benzimidazoles.
• Regiodirected synthesis of polyfluoro-alkylated pyrimido[1,2-a]benzimidazoles
  作者：M. V. Goryaeva、Ya. V. Burgart、V. I. Saloutin、O. N. Chupakhin

  DOI：10.1007/s10593-012-1000-8

  日期：2012.5

  Conditions have been found for the regiodirected cyclization of 2-aminobenzimidazoles using ethyl 3-oxo-3-polyfluoroalkyl-2-ethoxymethylidenepropionates at the ethoxymethylidenefluoroacyl fragment to give ethyl pyrimidobenzimidazole-3-carboxylates.