1-(3,5-difluorobenzyl)-2-(3,5-difluorophenyl)-1H-benzo[d]imidazole | 1493791-56-2

• 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-(3,5-difluorobenzyl)-2-(3,5-difluorophenyl)-1H-benzo[d]imidazole
• CAS: 1493791-56-2
• 化学式: C₂₀H₁₂F₄N₂
• 分子量: 356.322
• InChiKey: PMKKESCRSORKFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,5-二氟苯甲醛 、 邻苯二胺 在 cerium(IV) oxide 作用下， 以 水 为溶剂， 反应 0.67h， 以88%的产率得到1-(3,5-difluorobenzyl)-2-(3,5-difluorophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media

  摘要：

  A series of substituted benzimidazoles, benzothiazoles, and benzoxazoles was synthesized by combining 1,2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, heteroaryl, aliphatic, alpha,beta-unsaturated aldehydes in the presence of nano ceria (CeO2) as an efficient heterogeneous catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.092

文献信息

• The synthesis and structure of an amazing and stable carbonized material Cu-PC@OFM and its catalytic applications in water with mechanism explorations
  作者：An-Qi Tian、Xiang-Hao Luo、Zhi-Lin Ren、Jun Zhao、Long Wang

  DOI：10.1039/d1nj00861g

  日期：——

  structure, but also the nano copper particles generated in situ significantly improve the catalytic performance and stability. It was disclosed that the copper-based catalyst material Cu-PC@OFM showed high catalytic activity in the borrowing hydrogen reaction and the synthesis of 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives with high yields in water. This copper catalytic system provided a much greener

  通过HRTEM，SEM，XRD，XPS和拉曼光谱以及氮吸附/解吸分析，合成并表征了一种令人惊奇且稳定的碳化八面体框架材料Cu-PC @ OFM。特别地，负载有纳米铜的碳基质载体不仅保持原始结构，而且原位产生的纳米铜颗粒也显着改善了催化性能和稳定性。公开了铜基催化剂材料Cu-PC @ OFM在借位氢反应和1-苄基-2-芳基-1 H-苯并[ d]的合成中显示出高催化活性。]咪唑衍生物在水中的产率高。该铜催化体系为合成功能化的胺和1-苄基-2-芳基-1 H-苯并[ d ]咪唑在水中具有良好的回收性能提供了更加绿色和高效的催化剂，这是Cu-的第一个实例。 PC @ OFM材料催化的1-苄基-2-芳基-1 H-苯并[ d ]咪唑的合成。此外，通过一些条件控制实验，氘标记实验和中间体分离实验，提出了合理的反应机理。
• BINAP-copper supported by hydrotalcite as an efficient catalyst for the borrowing hydrogen reaction and dehydrogenation cyclization under water or solvent-free conditions
  作者：Zhaojun Xu、Xiaoli Yu、Xinxin Sang、Dawei Wang

  DOI：10.1039/c8gc00557e

  日期：——

  A BINAP-Cu system supported by hydrotalcite has been developed and proved to be a highly efficient catalyst for the atom-efficient and green borrowing hydrogen reaction and dehydrogenative cyclization. This BINAP-Cu complex supported by hydrotalcite is highly air-stable and can be recycled at least five times under solvent-free conditions. Notably, 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives could

  已经开发了由水滑石支撑的BINAP-Cu系统，并被证明是一种高效的催化剂，用于原子效率高的绿色借入氢反应和脱氢环化反应。这种由水滑石负载的BINAP-Cu络合物具有高度的空气稳定性，在无溶剂条件下可以循环至少五次。值得注意的是，第一次以水为溶剂仅一步即可由醇合成1-苄基-2-芳基-1 H-苯并[ d ]咪唑衍生物。这为在水或无溶剂条件下以高收率合成官能化的胺，酮和1-苄基-2-芳基-1 H-苯并[ d ]咪唑衍生物提供了一种更加绿色有效的催化方法。
• 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。
• A Zirconium Indazole Carboxylate Coordination Polymer as an Efficient Catalyst for Dehydrogenation‐Cyclization and Oxidative Coupling Reactions
  作者：Xinxin Sang、Xinyu Hu、Rong Tao、Yilin Zhang、Haiyan Zhu、Dawei Wang

  DOI：10.1002/cplu.201900349

  日期：2020.1

  The development of efficient ligands is well recognized to be crucial for the widespread applications of coordination polymers. Herein, we reported the preparation, structural characterisation and catalytic applications of zirconium (Ⅳ) coordination polymer (Zr‐IDA), which was derived from 1‐(carboxymethyl)‐1H‐indazole‐5‐carboxylic acid. The Zr‐IDA catalyst was composed of porous and highly crystallized

  有效配体的开发对于配位聚合物的广泛应用至关重要。本文中，我们报道了衍生自1-（羧甲基）-1H-吲唑-5-羧酸的锆（Ⅳ）配位聚合物（Zr-IDA）的制备，结构表征和催化应用。Zr-IDA催化剂由多孔且高度结晶的颗粒组成，其准球形形态在100 nm附近，并且FT-IR和XPS揭示Zr与O和N均具有配位作用。令我们高兴的是，Zr-IDA催化剂在苄基氰化物与叔丁基过氧化氢的氧化偶合中获得了优异的活性，选择性和稳定性，从而得到叔丁基过酸酯，邻苯二胺与芳香醇的脱氢环化得到了芳烃。 1，2-二取代的苯并咪唑衍生物。进行了进一步的研究，以阐明反应机理并深入了解已开发的催化系统。