1-(4'-trifluoromethoxyphenyl)methyl-2-(4"-trifluoromethoxyphenyl)benzimidazole

• 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'-trifluoromethoxyphenyl)methyl-2-(4"-trifluoromethoxyphenyl)benzimidazole
• 英文别名: 1-(4-(trifluoromethoxy)benzyl)-2-(4-(trifluoromethoxy)phenyl)benzimidazole；2-[4-(Trifluoromethoxy)phenyl]-1-[[4-(trifluoromethoxy)phenyl]methyl]benzimidazole
• 化学式: C₂₂H₁₄F₆N₂O₂
• 分子量: 452.356
• InChiKey: USFLLYIPZKRUAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  对三氟甲氧基苯甲醛 、 邻苯二胺 在 mesoporous mixed metal oxide nanocrystals of Al₂O₃-Fe₂O₃, Al₂O₃-V₂O₅, Al₂O₃-CuO 作用下， 反应 0.01h， 以89%的产率得到1-(4'-trifluoromethoxyphenyl)methyl-2-(4"-trifluoromethoxyphenyl)benzimidazole
  参考文献：
  名称：

  Mesoporous mixed metal oxide nanocrystals: Efficient and recyclable heterogeneous catalysts for the synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles

  摘要：

  Present communication elicits the use of mesoporous mixed metal oxide nanocrystals of Al2O3-Fe2O3. Al2O3-V2O5 and Al2O3-CuO as heterogeneous catalysts for the preparation of series of medicinally significant 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles. These nanocrystalline catalysts exhibited remarkable catalytic activity with a high substrate to catalyst weight ratio (20:1) to achieve the synthetic targets in the range of yield 81-96%. The solvent-free microwave assisted synthesis of these compounds was an advantageous way which resulted in excellent yields in much lesser time (0.75-1.5 min) in comparison to conventional heating. The use of catalyst in eco-friendly green protocol and its reusability up to four cycles with similar catalytic response are the unique features of the heterogeneous catalysis. This protocol provided greater selectivity, cost-efficiency, clean reaction profiles, simple work-up procedure and high yields. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.03.027

文献信息

• Application of Sulfamic Acid as an Eco-friendly Catalyst in an Expedient Synthesis of Benzimidazoles
  作者：Peter Seeberger、Manas Chakrabarty、Sulakshana Karmakar、Ajanta Mukherji、Shiho Arima、Yoshihiro Harigaya

  DOI：10.3987/com-06-10692

  日期：——
• Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents
  作者：Prabal Bandyopadhyay、Manisha Sathe、S. Ponmariappan、Arti Sharma、Pratibha Sharma、A.K. Srivastava、M.P. Kaushik

  DOI：10.1016/j.bmcl.2011.10.034

  日期：2011.12

  Present communication deals with the in vitro time point quantitative antibacterial evaluation of newly synthesized 1,2-disubstituted benzimidazoles (3a-p) and 2-substituted benzothiazoles (5a-h) against Gram-positive bacteria Staphylococcus aureus, Bacillus cereus, and Gram-negative bacteria Vibrio cholerae, Shigella dysenteriae and Escherichia coli. These compounds were synthesized under mild reaction conditions using Al(2)O(3)-Fe(2)O(3) nanocrystals as heterogeneous catalyst. Bio-evaluation studies revealed that, compounds 3a, 5a and 5d exhibited moderate to good antibacterial activity against all the tested bacterial stains. The compounds 3a, 3f and 5a have shown enhanced inhibitory activity compared with standard antibacterial drug ciprofloxacin against V. cholerae, B. cereus, and S. dysenteriae, respectively. Additionally, the compounds 3a, 3e, 3f, 3h and 5b displayed complete bactericidal activity within 24 h, whereas ciprofloxacin took 48 h to kill those bacteria completely. (C) 2011 Elsevier Ltd. All rights reserved.
• Mesoporous mixed metal oxide nanocrystals: Efficient and recyclable heterogeneous catalysts for the synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles
  作者：Prabal Bandyopadhyay、Manisha Sathe、G.K. Prasad、Pratibha Sharma、M.P. Kaushik

  DOI：10.1016/j.molcata.2011.03.027

  日期：2011.5

  Present communication elicits the use of mesoporous mixed metal oxide nanocrystals of Al2O3-Fe2O3. Al2O3-V2O5 and Al2O3-CuO as heterogeneous catalysts for the preparation of series of medicinally significant 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles. These nanocrystalline catalysts exhibited remarkable catalytic activity with a high substrate to catalyst weight ratio (20:1) to achieve the synthetic targets in the range of yield 81-96%. The solvent-free microwave assisted synthesis of these compounds was an advantageous way which resulted in excellent yields in much lesser time (0.75-1.5 min) in comparison to conventional heating. The use of catalyst in eco-friendly green protocol and its reusability up to four cycles with similar catalytic response are the unique features of the heterogeneous catalysis. This protocol provided greater selectivity, cost-efficiency, clean reaction profiles, simple work-up procedure and high yields. (C) 2011 Elsevier B.V. All rights reserved.