1-{4-(1H-benzimidazol-2-ylamino)pyrimido[1,2-a]benzimidazol-3-yl}-2,2,2-trifluoroethan-1-one | 1240485-98-6

• 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: 1-{4-(1H-benzimidazol-2-ylamino)pyrimido[1,2-a]benzimidazol-3-yl}-2,2,2-trifluoroethan-1-one
• 英文别名: 1-{4-(1h-Benzimidazol-2-ylamino)pyrimido-[1,2-a]benzimidazol-3-yl}-2,2,2-trifluoroethan-1-one；1-[4-(1H-benzimidazol-2-ylamino)pyrimido[1,2-a]benzimidazol-3-yl]-2,2,2-trifluoroethanone
• CAS: 1240485-98-6
• 化学式: C₁₉H₁₁F₃N₆O
• 分子量: 396.331
• InChiKey: RNBBNBOCOSQLKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  8

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 1,4-二氧六环 为溶剂， 以65%的产率得到ethyl 4-trifluoromethylpyrimido[1,2-a]benzimidazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of pyrimido[1,2-a]benzimidazoles from ethyl 2-ethoxymethylidene-3-oxo-3-(polyfluoroalkyl)propionates

  摘要：

  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.

  DOI：

  10.1134/s1070428010030231

文献信息

• 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.