1-(4-(trifluoromethyl)benzyl)-2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole | 1351357-02-2

• 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-(trifluoromethyl)benzyl)-2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole
• 英文别名: 1-[4-(trifluoromethyl)benzyl]-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole；2-[4-(Trifluoromethyl)phenyl]-1-[[4-(trifluoromethyl)phenyl]methyl]benzimidazole
• CAS: 1351357-02-2
• 化学式: C₂₂H₁₄F₆N₂
• 分子量: 420.357
• InChiKey: YVYXTHGQLJKDEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 邻苯二胺 在 perchloric acid on silica gel 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以85%的产率得到1-(4-(trifluoromethyl)benzyl)-2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity

  摘要：

  在形成1,2-二取代苯并咪唑的反应中，已经实现了选择性控制，该反应是对邻苯二胺与醛类在固态酸催化剂的存在下进行的，同时选择了合适的反应介质。研究发现，吸附在硅胶上的高氯酸（HClO4–SiO2）是合成1,2-二取代苯并咪唑在室温下使用乙醇的最有效催化体系。除了催化剂和溶剂之外，醛的电子和空间因素以及邻苯二胺的电子因素也是决定选择性的显著因素。对于1,2-二取代苯并咪唑的形成机制的理解也已被概述，这将有助于解释在设定实验参数下选择性控制的来源。

  DOI：

  10.1039/c2ra21994h

文献信息

• An organoantimony nitrate complex with azastibocine framework as water tolerant Lewis acid catalyst for the synthesis of 1,2‐disubstitued benzimidazoles
  作者：Cong Zhou、Jian Lei、Yongping Liu、Chak‐Tong Au、Yi Chen、Shuang‐Feng Yin

  DOI：10.1002/aoc.5881

  日期：2020.10

  techniques such as NMR spectra, TG‐DSC, and X‐ray diffraction. It was found that the complex 2 exhibits relatively strong Lewis acidity (3.3 < Ho ≤ 4.8) and could be employed as a water tolerant Lewis acid catalyst for the synthesis of synthetically valuable benzimidazole derivatives starting from aldehydes and arylenediamines. This catalytic system shows excellent tolerance toward a wide variety of functional

  合成了一种新型的6-环己基-6,7-二氢二苯并[ c，f ] [ 1,5 ]氮杂阿司匹林-12（5H）-硝酸硝酸根（2）的有机锑配合物，并通过NMR光谱，TG- DSC和X射线衍射。结果发现，复合2只表现出相对强的路易斯酸性（3.3 <何≤4.8），并且可以用作用于从醛和arylenediamines开始合成有价值的苯并咪唑衍生物的合成中的水耐受性路易斯酸催化剂。该催化体系对各种官能团（例如甲基，甲氧基，氟，氯，溴，硝基，氰基，三氟甲基，1-萘醛，糠醛和n-丁基，再加上5倍规模的合成的简便可重复使用性。
• Nano Copper(0)-Stabilized on Alumina: Efficient and Recyclable Heterogeneous Catalyst for Chemoselective Synthesis of 1,2-Disubstituted Benzimidazoles and Quinoxalines in Aqueous Medium
  作者：Jaya Pogula、Soumi Laha、Pravin R. Likhar

  DOI：10.1007/s10562-017-2166-6

  日期：2017.11

  communication elicits the use of copper nanoparticles on aluminium oxide derived from Cu–Al hydrotalcite as a heterogeneous catalyst in the green and operationally simple approach for the synthesis of selective 1,2-disubstituted benzimidazoles and quinoxaline. Wide ranges of substituted o-phenylenediamines and aldehydes or α-bromo ketones were used to achieve the desired products using water as the reaction

  本通讯引出在源自 Cu-Al 水滑石的氧化铝上使用铜纳米颗粒作为非均相催化剂，以绿色且操作简单的方法合成选择性 1,2-二取代苯并咪唑和喹喔啉。使用范围广泛的取代邻苯二胺和醛或 α-溴酮，以水作为反应介质来获得所需的产物。催化剂的可回收性和可重复使用性是这种环保绿色协议的显着特征。图文摘要描述了一种在室温下在 Cu (0) / Al2O3 催化剂存在下合成苯并咪唑和喹喔啉的简单有效方法。
• Hydrogen-Bond-Driven Electrophilic Activation for Selectivity Control: Scope and Limitations of Fluorous Alcohol-Promoted Selective Formation of 1,2-Disubstituted Benzimidazoles and Mechanistic Insight for Rationale of Selectivity
  作者：Rajesh Chebolu、Damodara N. Kommi、Dinesh Kumar、Narendra Bollineni、Asit K. Chakraborti

  DOI：10.1021/jo301793z

  日期：2012.11.16

  Hydrogen-bond-driven electrophilic activation for selectivity control during competitive formation of 1,2-disubstituted and 2-substituted benzimidazoles from o-phenylenediamine and aldehydes is reported. The fluorous alcohols trifluoroethanol and hexafluoro-2-propanol efficiently promote the cyclocondensation of o-phenylenediamine with aldehydes to afford selectively the 1,2-disubstituted benzimidazoles at rt in short times. A mechanistic insight is invoked by NMR, mass spectrometry, and chemical studies to rationalize the selectivity. The ability of the fluorous alcohols in promoting the reaction and controlling the selectivity can be envisaged from their better hydrogen bond donor (HBD) abilities compared to that of the other organic solvents as well as of water. Due to the better HBD values, the fluorous alcohols efficiently promote the initial bisimine formation by electrophilic activation of the aldehyde carbonyl. Subsequently the hydrogen-bond-mediated activation of the in situ-formed bisimine triggers the rearrangement via 1,3-hydride shift to form the 1,2-disubstituted benzimidazoles.
• 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.
• Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity
  作者：Dinesh Kumar、Damodara N. Kommi、Rajesh Chebolu、Sanjeev K. Garg、Raj Kumar、Asit K. Chakraborti

  DOI：10.1039/c2ra21994h

  日期：——

  Selectivity control during the formation of 1,2-disubstituted benzimidazoles has been achieved for the reaction of o-phenylenediamine with aldehydes in the presence of solid supported protic acids as catalysts and choosing an appropriate reaction medium. Perchloric acid adsorbed on silica-gel (HClO4–SiO2) was found to be the most effective catalyst system for the synthesis of 1,2-disubstituted benzimidazoles in EtOH at rt. Apart from the catalyst and solvent, the electronic and steric factors of the aldehyde and the electronic factor of the o-phenylenediamine are also significant contributory factors in dictating the selectivity. An understanding of the mechanistic course of the formation of the 1,2-disubstituted benzimidazoles has been outlined that would rationalise the origin of selectivity control under the set experimental parameters.

  在形成1,2-二取代苯并咪唑的反应中，已经实现了选择性控制，该反应是对邻苯二胺与醛类在固态酸催化剂的存在下进行的，同时选择了合适的反应介质。研究发现，吸附在硅胶上的高氯酸（HClO4–SiO2）是合成1,2-二取代苯并咪唑在室温下使用乙醇的最有效催化体系。除了催化剂和溶剂之外，醛的电子和空间因素以及邻苯二胺的电子因素也是决定选择性的显著因素。对于1,2-二取代苯并咪唑的形成机制的理解也已被概述，这将有助于解释在设定实验参数下选择性控制的来源。