1-(4-chlorobenzyl)-2-(4-chlorophenyl)-6-methyl-1H-benzo[d]imidazole | 77314-38-6

• 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-chlorobenzyl)-2-(4-chlorophenyl)-6-methyl-1H-benzo[d]imidazole
• 英文别名: 2-(4-Chlorophenyl)-1-[(4-chlorophenyl)methyl]-6-methylbenzimidazole
• CAS: 77314-38-6
• 化学式: C₂₁H₁₆Cl₂N₂
• 分子量: 367.277
• InChiKey: QKENJSHFNAOWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-benzyl-2-(p-chlorophenyl)-3-(p-chlorobenzyl)-5-methylbenzimidazoline 生成 1-(4-chlorobenzyl)-2-(4-chlorophenyl)-6-methyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  RAO, C. V. CHALAPATHI;REDDY, K. K.;RAO, N. V. SUBBA, INDIAN J. CHEM., 1980, 19, N 11, 967-969

  摘要：

  DOI：

文献信息

• Nickel-catalysed dehydrogenative coupling of aromatic diamines with alcohols: selective synthesis of substituted benzimidazoles and quinoxalines
  作者：Atanu Bera、Motahar Sk、Khushboo Singh、Debasis Banerjee

  DOI：10.1039/c9cc02319d

  日期：——

  The first nickel-catalysed dehydrogenative coupling of primary alcohols and ethylene glycol with aromatic diamines for selective synthesis of mono- and di-substituted benzimidazoles and quinoxalines is reported. The earth-abundant, non-precious and simple NiCl2/L1 system enables the synthesis of N-heterocycles releasing water and hydrogen gas as byproducts. Mechanistic studies involving deuterium labeling

  报道了伯醇和乙二醇与芳族二胺的首次镍催化的脱氢偶联，用于选择性合成单取代和二取代的苯并咪唑和喹喔啉。富含地球，不贵重且简单的NiCl 2 / L1系统可合成N杂环，释放出水和氢气作为副产物。进行了涉及氘标记实验和氢气定量测定的机理研究。
• Tunable Triazole-Phosphine-Copper Catalysts for the Synthesis of 2-Aryl-1<i>H</i> -benzo[d]imidazoles from Benzyl Alcohols and Diamines by Acceptorless Dehydrogenation and Borrowing Hydrogen Reactions
  作者：Zhaojun Xu、Duo-Sheng Wang、Xiaoli Yu、Yongchun Yang、Dawei Wang

  DOI：10.1002/adsc.201700179

  日期：2017.10.4

  activity. Mechanistic studies and deuterium labeling experiments indicated that the reactions proceeded by an initial and reversible alcohol dehydrogenation resulting in a copper hydride intermediate. This was also supported by the direct observation of a diagnostic copper hydride signal by solid‐state infrared spectroscopy. The TAP−Cu‐H complex showed absorptions at 912 cm−1 that could be assigned

  三唑-膦-铜配合物（TAP-Cu）已被合成并用作可调谐和有效的催化剂，用于选择性合成氟代2-芳基-1 H-苯并[d]咪唑和1-苄基-2-芳基1小时一步法制得的简单醇中的苯并[d]咪唑衍生物。TAP-Cu对脱氢和借用氢反应均显示出优异且可调节的催化活性，首次证明了80多个例子。观察到配体在催化剂活性中起关键作用。机理研究和氘标记实验表明，反应是通过初始且可逆的醇脱氢进行的，从而生成氢化铜中间体。固态红外光谱法直接观察氢化铜诊断信号也支持了这一点。TAP-Cu-H络合物在912 cm -1处显示吸收可以分配给氢化铜拉伸。此外，也成功地进行了中间双亚胺的直接捕集。
• Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines
  作者：Ali Maleki、Nakisa Ghamari、Maryam Kamalzare

  DOI：10.1039/c3ra47366j

  日期：——

  An environmentally benign and clean biopolymer-based heterogeneous nanocatalyst was prepared and its properties and morphology were characterized using scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX) and X-ray diffraction (XRD). Then, its catalytic activity was investigated in two important organic reactions. In these reactions, efficient and selective syntheses of 1,2-disubstituted benzimidazole and 1,5-benzodiazepine derivatives were carried out using 1,2-diamines and aldehydes or ketones in the presence of a catalytic amount of magnetically recoverable chitosan-supported iron oxide nanoparticles (Fe3O4/chitosan), as a biodegradable nanocomposite, in ethanol at ambient temperature in high yields. The Fe3O4/chitosan nanocatalyst can be recovered easily and reused without any significant loss of the catalytic activity.

  制备了一种环境友好且清洁的生物聚合物基异质纳米催化剂，并通过扫描电子显微镜（SEM）、能量色散X射线光谱（EDX）和X射线衍射（XRD）对其性质和形态进行了表征。随后，研究了其在两种重要有机反应中的催化活性。在这些反应中，使用1,2-二胺和醛或酮在催化量的可磁回收壳聚糖支持铁氧化物纳米颗粒（Fe3O4/壳聚糖）的存在下，在室温下的乙醇中高效且选择性地合成了1,2-取代的苯并咪唑和1,5-苯并二氮杂卓衍生物。Fe3O4/壳聚糖纳米催化剂可以轻松回收并重复使用，且没有显著的催化活性损失。
• Heterogenizing a Homogeneous Nickel Catalyst Using Nanoconfined Strategy for Selective Synthesis of Mono- and 1,2-Disubstituted Benzimidazoles
  作者：Shadab、Gargi Dey、Motahar Sk、Debasis Banerjee、Arshad Aijaz

  DOI：10.1021/acs.inorgchem.1c02017

  日期：2021.11.1

  homogeneous Ni-phenanthroline catalyst was successfully immobilized into the cavities of a metal–organic framework, ZIF-8. The as-synthesized heterogeneous catalyst, Ni-Phen@ZIF, represents the first MOF based catalyst that enables dehydrogenative coupling of alcohols with aromatic diamines for selective synthesis of both mono- and 1,2-disubstituted benzimidazoles. The catalyst survived under harsh basic

  均相 Ni-菲咯啉催化剂成功地固定在金属有机骨架 ZIF-8 的空腔中。合成的多相催化剂 Ni-Phen@ZIF 代表了第一种基于 MOF 的催化剂，它能够使醇与芳香二胺脱氢偶联，以选择性合成单和 1,2-二取代苯并咪唑。该催化剂在恶劣的碱性条件下仍然存在，通过 SEM、TEM、BET、PXRD 和 EDX 元素映射进行表征。通过 TPD 分析和动力学实验证实，纳米限制的 Ni-菲咯啉络合物的存在和在 Ni-Phen@ZIF 结构催化过程中形成额外的路易斯酸位点，可能是导致更高活性和选择性的原因。
• 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。