2-(2',3',4'-Trimethoxy)phenylbenzimidazole

• 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: 2-(2',3',4'-Trimethoxy)phenylbenzimidazole
• 英文别名: 2-(2,3,4-trimethoxyphenyl)-1H-benzimidazole
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: ZMRGQVVZKQOXCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2',3',4'-Trimethoxy)phenylbenzimidazole 、 苯丙炔酸乙酯 在 copper(II) acetate monohydrate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以54%的产率得到Ethyl 1,2,3-trimethoxy-6-phenylbenzimidazolo[2,1-a]isoquinoline-5-carboxylate
  参考文献：
  名称：

  Ruthenium-catalyzed benzimidazoisoquinoline synthesis via oxidative coupling of 2-arylbenzimidazoles with alkynes

  摘要：

  Synthesis of a fused bis-heterocyclic framework, benzimidazoisoquinoline, has been achieved using Ru-catalyzed reaction of alkynes with 2-aryl benzimidazoles in the presence of Cu salts. The method provides an easy access for the generation of a library of benzimidazoisoquinoline derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.106
• 作为产物：
  描述：

  邻苯二胺 、 2,3,4-三甲氧基苯甲醛 在 sodium sulfite 作用下， 以 水 为溶剂， 生成 2-(2',3',4'-Trimethoxy)phenylbenzimidazole
  参考文献：
  名称：

  Use of benzimidazole derivatives as light protection filters

  摘要：

  本发明涉及使用公式I的苯并咪唑衍生物，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和Ar的含义如权利要求1所述，作为化妆品配方中的光保护过滤剂，其中至少有一个基团R.sup.1至R.sup.4或Ar的烷基或烷氧基取代基含有至少4个C原子。

  公开号：

  US05501850A1

文献信息

• Direct synthesis of benzimidazoles by Pd(II) N^N^S-pincer type complexes via acceptorless dehydrogenative coupling of alcohols with diamines
  作者：Pennamuthiriyan Anandaraj、Rengan Ramesh、Jan Grzegorz Malecki

  DOI：10.1016/j.jorganchem.2022.122577

  日期：2023.2

  geometry of the synthesized complexes 1 and 2 was confirmed by single-crystal X-ray diffraction study. A wide range of benzimidazole derivatives (32 examples) up to 94% isolated yield has been derived via acceptorless dehydrogenative coupling of primary alcohols with derivatives of o-phenylenediamines. The present protocol operates smoothly with only 1 mol% catalyst loading. Furthermore, the mechanistic

  报道了一种通过钯催化剂对伯醇进行无受体脱氢偶联来构建取代苯并咪唑的可持续合成方法。合成了三种新的非经典对称 Pd(II) N^N^S 钳状配合物 ( 1–3 )，并通过光谱（FT-IR、UV-vis、NMR 和 ESI-MS）和分析技术对其进行了表征。此外，通过单晶 X 射线衍射研究证实了合成配合物1和2的扭曲方形平面几何形状。通过伯醇与o的衍生物的无受体脱氢偶联，衍生出范围广泛的苯并咪唑衍生物（32 个实例），分离产率高达 94%- 苯二胺。本协议运行平稳，催化剂负载量仅为 1 mol%。此外，在对照实验的帮助下进行的机理研究表明，反应是通过原位生成醛中间体进行的，并生成氢气和水作为唯一的副产物。
• Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres
  作者：Gabriel Navarrete-Vázquez、Hermenegilda Moreno-Diaz、Francisco Aguirre-Crespo、Ismael León-Rivera、Rafael Villalobos-Molina、Omar Muñoz-Muñiz、Samuel Estrada-Soto

  DOI：10.1016/j.bmcl.2006.05.082

  日期：2006.8

  A simple, fast, and efficient method for the preparation of several 2-(alkyloxyaryl)-1H-benzimidazole derivatives is reported. Compounds were synthesized through a rapid one-pot three component reaction via microwave irradiation, starting from commercially available aldehydes and o-phenylenediamine, in the presence of Na2S2O5 and solvent-free conditions. The design of these compounds explore the hypothesis that the stilbene framework could be mimicked with an appropriate 2-(Alkyloxyphenyl)benzimidazole scaffold. This framework has a similar structural motif as the 6-phenyinaphthalene and behaves like stilbene bioisosteres. The spasmolytic activity of these compounds was recorded using isolated rat ileum test. Compound 12 was the most active of the series, showing an IC50 of 1.19 mu M. (c) 2006 Elsevier Ltd. All rights reserved.
• VERWENDUNG VON BENZIMIDAZOL-DERIVATEN ALS LICHTSCHUTZFILTER
  申请人：MERCK PATENT GmbH

  公开号：EP0581955B1

  公开（公告）日：1996-10-16