1-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)-1H-benzo[d]imidazole | 2562-67-6

• 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-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)-1H-benzo[d]imidazole
• 英文别名: 1-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)-1H-benzimidazole；2-(3,4-dimethoxyphenyl)-1-[(3,4-dimethoxyphenyl)methyl]benzimidazole
• CAS: 2562-67-6
• 化学式: C₂₄H₂₄N₂O₄
• mdl: MFCD02630712
• 分子量: 404.466
• InChiKey: DVLPFAGTQLYEDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  589.4±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-Benzenediamine, N,N'-bis[(3,4-dimethoxyphenyl)methylene]- 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以93%的产率得到1-(3,4-dimethoxybenzyl)-2-(3,4-dimethoxyphenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Facile Synthesis of 1,2-Disubstituted Benzimidazoles Usingp-Toluenesulfonic Acid through Grinding Method

  摘要：

  An efficient synthetic method for the highly selective synthesis of pharmacologically active 1,2-disubstituted benzimidazole derivatives fromo-phenylenediamine and various aromatic aldehydes catalyzed byp-toluenesulfonic acid through grinding under solvent-free condition is described. The reaction requires the catalyst only during the conversion of intermediateN,N '-dibenzylidene-o-phenylenediamine into the desired product. The products were obtained within a short time with good yields by using only a mortar and pestle, which makes the proposed method convenient and cost-effective.

  DOI：

  10.1134/s1070428020090201

文献信息

• A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
  作者：Mudzuli Maphupha、Wanyama P. Juma、Charles B. de Koning、Dean Brady

  DOI：10.1039/c8ra07377e

  日期：——

  Green chemistry: laccase in acetonitrile and buffer in the presence of O₂ can synthesise benzimidazoles and benzothiazoles in good yields.

  绿色化学：在乙腈和缓冲液中，存在氧气的情况下，漆酶可以合成苯并咪唑和苯并噻唑，产率较高。
• Chemoselective reduction of nitroaromatics using recyclable alumina-supported nickel nanoparticles in aqueous medium—exploration to one pot synthesis of benzimidazoles
  作者：Avishek Ghatak、Sanjay Bhar

  DOI：10.1080/00397911.2021.2024853

  日期：2022.2.1

  protocol for chemoselective and regioselective reduction of nitroaromatics in water has been achieved using easily accessible alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst. Various sensitive substituents like allyloxy, benzyloxy, t-butyldimethylsilyloxy, hydroxymethyl, alkoxycarbonyl, formyl, keto, carboxylic acid, chloro, bromo, azo and cyano were tolerated in

  摘要 使用易于获得的氧化铝负载的镍纳米粒子作为稳定的可回收多相催化剂，实现了一种经济且生态兼容的合成方案，用于化学选择性和区域选择性还原水中的硝基芳烃。在上述方案中允许使用各种敏感的取代基，如烯丙氧基、苄氧基、叔丁基二甲基甲硅烷氧基、羟甲基、烷氧基羰基、甲酰基、酮基、羧酸、氯、溴、偶氮和氰基。该方法已扩展到通过 2-硝基苯胺与不同取代的苯甲醛的一锅还原缩合来构建咪唑衍生物。一些合成的咪唑已被用作抗菌剂、抗血小板剂和抗血栓剂。
• A simple and straightforward synthesis of substituted 2-arylbenzimidazoles over silica gel
  作者：Amit K. Chaturvedi、Arvind S. Negi、Puja Khare

  DOI：10.1039/c3ra22435j

  日期：——

  A solid phase strategy for the synthesis of substituted 2-arylbenzimidazoles over silica gel has been achieved starting from their corresponding o-phenylenediamines 1 and aromatic aldehydes 2. The reaction is very simple, convenient and straightforward, and the products are obtained in moderate to high yields (49–91%).

  用固相策略合成取代的2-芳基苯并咪唑 硅石从它们相应的邻苯二胺1和芳香醛2开始已经获得了凝胶。该反应非常简单，方便和直接，并且以中等至高收率（49–91％）获得了产物。
• A Green Route for the One-Pot Synthesis of 1,2-Disubstituted Benzimidazoles Using Iron(III) Phosphate under Solventless Conditions
  作者：F. K. Behbahani、Parisa Ziaei

  DOI：10.1002/cjoc.201180461

  日期：2012.1

  1,2‐Disubstituted benzimidazoles are selectively synthesized in high yields under extremely mild conditions via the condensation of o‐phenylenediamine derivatives with aldehyde derivatives using catalytic amount of iron(III) phosphate under solvent‐free conditions. The use of readily available iron(III) phosphate as a reusable and recyclable catalyst makes this process quite simple, convenient, and

  在极温和的条件下，通过催化量的磷酸铁（III）在无溶剂条件下邻苯二胺衍生物与醛衍生物的缩合，可以高产率选择性合成1,2-二取代的苯并咪唑。使用现成的磷酸铁（III）作为可重复使用和可循环使用的催化剂，使该过程非常简单，方便且对环境友好。
• Practical, Ecofriendly, and Chemoselective Method for the Synthesis of 2-Aryl-1-arylmethyl-1<i>H</i>-benzimidazoles Using Amberlite IR-120 as a Reusable Heterogeneous Catalyst in Aqueous Media
  作者：Saikat Das Sharma、Dilip Konwar

  DOI：10.1080/00397910802448440

  日期：2009.2.25

  environmentally benign method has been developed for the exclusive formation of biologically significant 2-aryl-1-arylmethyl-1H-benzimidazoles under the heterogeneous catalysis of Amberlite IR-120 in aqueous media in excellent yields. The catalyst is recyclable without loss of activity.

  摘要 开发了一种简单、高效且环境友好的方法，用于在水介质中 Amberlite IR-120 的多相催化下以优异的产率独家形成具有生物学意义的 2-芳基-1-芳基甲基-1H-苯并咪唑。该催化剂可回收而不会损失活性。