1-[4-(benzyloxy)benzyl-2-4-(benzyloxy)phenyl]-1H-benzimidazole | 1407156-92-6

• 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-(benzyloxy)benzyl-2-4-(benzyloxy)phenyl]-1H-benzimidazole
• 英文别名: 2-(4-Phenylmethoxyphenyl)-1-[(4-phenylmethoxyphenyl)methyl]benzimidazole；2-(4-phenylmethoxyphenyl)-1-[(4-phenylmethoxyphenyl)methyl]benzimidazole
• CAS: 1407156-92-6
• 化学式: C₃₄H₂₈N₂O₂
• 分子量: 496.609
• InChiKey: FCEMHVONZHWGRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 邻苯二胺 在 perchloric acid on silica gel 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到1-[4-(benzyloxy)benzyl-2-4-(benzyloxy)phenyl]-1H-benzimidazole
  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

• 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。
• 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.
• Exploring the Synthetic and Antioxidant Potential of 1,2‐Disubstituted Benzimidazoles using [Et₃NH][HSO₄] Ionic Liquid Catalyst
  作者：Nusrat Sahiba、Pankaj Teli、Priyadarshi Meena、Shikha Agarwal

  DOI：10.1002/cbdv.202301159

  日期：——

  intermolecular C−N bond formation for 1,2-disubstituted benzimidazole synthesis was achieved by the reaction of OPD and substituted aldehydes at ambient reaction conditions. Operational simplicity, use of easily available substrate and reagents, good yields (74–95 %) in short reaction time (4–18 min), simple work-up, and column chromatographic free synthesis are the remarkable features of this new protocol. The

  通过OPD和取代醛在环境反应条件下的反应，实现了[Et 3 NH][HSO 4 ]离子液体催化的1,2-二取代苯并咪唑合成的分子间CN键形成。操作简单、使用容易获得的底物和试剂、短反应时间（4-18 分钟）内的高产率（74-95%）、简单的后处理以及无需柱色谱合成是该新方案的显着特征。 [Et 3 NH][HSO 4 ]离子液体作为一种绿色、廉价的催化剂，具有良好的可回收性以及与多种具有杂原子、吸电子和释放电子基团的官能团的相容性，其适用性表现出可持续性、生态性和环保性。 -当前方法的友好性和效率。此外，使用 DPPH 和 ABTS 测定对合成化合物进行抗氧化研究很有吸引力，并且几种合成化合物显示出显着的抗氧化活性。