2-(3-Oxo-4,4,4-trifluorobutanoyl)-1-methylbenzimidazole | 229317-78-6

• 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: 2-(3-Oxo-4,4,4-trifluorobutanoyl)-1-methylbenzimidazole
• 英文别名: 4,4,4-Trifluoro-1-(1-methylbenzimidazol-2-yl)butane-1,3-dione
• CAS: 229317-78-6
• 化学式: C₁₂H₉F₃N₂O₂
• mdl: MFCD12621847
• 分子量: 270.211
• InChiKey: DYEMPXAZRKVWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-Oxo-4,4,4-trifluorobutanoyl)-1-methylbenzimidazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以74%的产率得到5-Hydroxy-3-(1-methylbenzimidazol-2-yl)-5-trifluoromethyl-4,5-dihydropyrazole
  参考文献：
  名称：

  Formation and dehydration of a series of 5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles

  摘要：

  Reaction of five (3-oxo-4,4,4-trifluorobutanoyl)heterocycles with hydrazine hydrate under mild conditions gave the corresponding 3-heterocyclyl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles. Thermal elimination of water from the 3-(thien-2-yl), 3-(pyridin-2-yl) and 3-(pyridin-4-yl) compounds readily gave the corresponding pyrazoles but acid catalysis was required to form 3-(benzothiazol-2-yl)-5-trifluoromethylpyrazole and 3-(1-methylbenzimidazol-2-yl)-5-trifluoromethylpyrazole. More forcing conditions were required for the analogous dehydration/aromatisations giving 3,5-bis(trifluoromethyl)-1-(4-nitrophenyl)pyrazole and 3,5-bis(trifluoromethyl)-1-pentafluorophenylpyrazole. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00011-1
• 作为产物：
  描述：

  三氟乙酸乙酯 、 1-(1-甲基-1H-苯并咪唑-2-基)乙酮 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以34%的产率得到2-(3-Oxo-4,4,4-trifluorobutanoyl)-1-methylbenzimidazole
  参考文献：
  名称：

  Formation and dehydration of a series of 5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles

  摘要：

  Reaction of five (3-oxo-4,4,4-trifluorobutanoyl)heterocycles with hydrazine hydrate under mild conditions gave the corresponding 3-heterocyclyl-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazoles. Thermal elimination of water from the 3-(thien-2-yl), 3-(pyridin-2-yl) and 3-(pyridin-4-yl) compounds readily gave the corresponding pyrazoles but acid catalysis was required to form 3-(benzothiazol-2-yl)-5-trifluoromethylpyrazole and 3-(1-methylbenzimidazol-2-yl)-5-trifluoromethylpyrazole. More forcing conditions were required for the analogous dehydration/aromatisations giving 3,5-bis(trifluoromethyl)-1-(4-nitrophenyl)pyrazole and 3,5-bis(trifluoromethyl)-1-pentafluorophenylpyrazole. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00011-1