1-(3,4,5-trimethoxybenzyl)-2-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazole | 205755-89-1

• 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-(3,4,5-trimethoxybenzyl)-2-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazole
• 英文别名: 1-(3,4,5-trimethoxybenzyl)-2-(3,4,5-trimethoxyphenyl)-1H-benzimidazole；2-(3,4,5-trimethoxyphenyl)-1-[(3,4,5-trimethoxyphenyl)methyl]benzimidazole
• CAS: 205755-89-1
• 化学式: C₂₆H₂₈N₂O₆
• 分子量: 464.518
• InChiKey: QAAROVZFKLWAGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 邻苯二胺 在 sodium fluoride 作用下， 以 溶剂黄146 为溶剂， 以70 %的产率得到1-(3,4,5-trimethoxybenzyl)-2-(3,4,5-trimethoxyphenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  氟化钠辅助、溶剂控制的区域选择性合成具有不同取代基的2-取代和1,2-二取代苯并咪唑，并揭示了机理见解

  摘要：

  在氟化钠（NaF）存在下，在两种不同的极性溶剂中，苯二胺衍生物与不同的醛反应，实现了N1和C2位具有相似取代基的2-取代苯并咪唑和1,2-二取代苯并咪唑的区域选择性形成。该方法简单、经济、适用范围广。当使用4.76mol%的NaF作为催化剂时，该方法有助于在无水二甲基甲酰胺中形成2-取代的苯并咪唑和在冰乙酸中以优异的收率形成具有相似取代基的1,2-二取代的苯并咪唑。此外，我们还证明了利用一锅法合成在 N1 和 C2 位具有不同取代基的 1,2-二取代苯并咪唑，无需分离中间体 2-取代苯并咪唑。除了光谱研究之外，还使用单晶 X 射线衍射分析证实了 1,2-二取代苯并咪唑 () 的结构。这些发现强调了我们生产苯并咪唑类药物分子方法的实际可行性。

  DOI：

  10.1016/j.molstruc.2024.137935

文献信息

• 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。
• Zn-Proline Catalyzed Selective Synthesis of 1,2-Disubstituted Benzimidazoles in Water
  作者：Varala Ravi、Enugala Ramu、Kotra Vijay、Adapa Srinivas Rao

  DOI：10.1248/cpb.55.1254

  日期：——

  Zn-proline (5 mol%) performs as a novel water-soluble and recyclable Lewis acid catalyst for the selective synthesis of 1,2-disubstituted benzimidazoles from wide range of substituted o-phenylenediamines and aldehydes in moderate to excellent isolated yields (42—92%) using water as solvent at ambient temperature.

  Zn-proline（5 mol%）作为一种新型水溶性和可回收的路易斯酸催化剂，可以在常温下以水为溶剂，从多种取代的邻苯二胺和醛中选择性合成1,2-二取代的苯并咪唑，得到了中到优良的分离产率（42%—92%）。
• Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation
  作者：Kumar Godugu、Venkata Divya Sri Yadala、Mohammad Khaja Mohinuddin Pinjari、Trivikram Reddy Gundala、Lakshmi Reddy Sanapareddy、Chinna Gangi Reddy Nallagondu

  DOI：10.3762/bjoc.16.156

  日期：——

  Natural dolomitic limestone (NDL) is employed as a heterogeneous green catalyst for the synthesis of medicinally valuable benzimidazoles, dihydropyrimidinones, and highly functionalized pyridines via C–N, C–C, and C–S bond formations in a mixture of ethanol and H2O under ultrasound irradiation. The catalyst is characterized by XRD, FTIR, Raman spectroscopy, SEM, and EDAX analysis. The main advantages

  天然白云质石灰石（NDL）被用作异质绿色催化剂，用于通过乙醇和H 2的混合物中C–N，C–C和C–S键的形成来合成具有药用价值的苯并咪唑，二氢嘧啶酮和高度官能化的吡啶O在超声波照射下。该催化剂通过XRD，FTIR，拉曼光谱，SEM和EDAX分析来表征。这种方法的主要优点包括广泛的底物范围，更清洁的反应曲线，较短的反应时间和优异的分离产率。该产品不需要色谱纯化，该催化剂可以重复使用七次。因此，与现有报道的催化剂相比，该催化剂是用于合成上述N-杂环的更绿色的替代物。
• 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。
• A novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity
  作者：Amit K. Chaturvedi、Amit Kumar Verma、Jay Prakash Thakur、Sudeep Roy、Shashi Bhushan Tripathi、Balagani Sathish Kumar、Sadiya Khwaja、Naresh K. Sachan、Ashok Sharma、Debabrata Chanda、Karuna Shanker、Dharmendra Saikia、Arvind S. Negi

  DOI：10.1016/j.bmc.2018.07.049

  日期：2018.8

  Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a-3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a-4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H (37)Rv, MIC at 16 mu M and 24 mu M respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.