2-(3,4-dimethylphenyl)-1H-benzo[d]imidazole | 897796-35-9

• 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-(3,4-dimethylphenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(3,4-dimethylphenyl)-1H-benzimidazole；2-(3,4-dimethylphenyl)benzimidazole
• CAS: 897796-35-9
• 化学式: C₁₅H₁₄N₂
• mdl: MFCD06092517
• 分子量: 222.29
• InChiKey: AFKXUOXOEGHSDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碘苯 、 2-(3,4-dimethylphenyl)-1H-benzo[d]imidazole 在 palladium diacetate 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以75%的产率得到6,7-dimethylbenzo[4,5]imidazo[1,2-f]phenanthridine
  参考文献：
  名称：

  Palladium(II)-Catalyzed Sequential C–H Arylation/Aerobic Oxidative C–H Amination: One-Pot Synthesis of Benzimidazole-Fused Phenanthridines from 2-Arylbenzimidazoles and Aryl Halides

  摘要：

  Starting from 2-arylbenzimidazoles and aryl halides, an efficient palladium-based catalytic method for the synthesis of benzimidazole-fused phenanthridines has been developed. This reaction sequence comprises intermolecular C-H arylation and intramolecular aerobic oxidative C-H amination, involving the rupture of two C-H bonds, one C-X bond, and one N-H bond in one pot. The Pd-II-Pd-IV-Pd-II and Pd-II-Pd-0-Pd-II catalytic cycles work together under the reported conditions to generate phenanthridines with diverse substituents.

  DOI：

  10.1021/jo502632b
• 作为产物：
  描述：

  N-phenyl-3,4-dimethylbenzamidine 在 phenyliodine(III) diacetate 、 caesium carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 1.5h， 以86%的产率得到2-(3,4-dimethylphenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  苯并咪唑的合成PIDA促进的直接C（SP2） ？N-Arylamidines的H酰亚胺化

  摘要：

  无金属合成从多元化的苯并咪唑的Ñ -arylamidines通过phenyliodine（III）二乙酸酯（PIDA）促进分子内的直接C（SP 2） ħ酰亚胺化得到了发展。反应可在0°C或环境温度下顺利进行，以良好至极好的收率提供所需的产物。也可以实现通常通过类似的Pd或Cu催化方法无法获得的2烷基或2烷基稠合苯并咪唑的合成。

  DOI：

  10.1002/chem.201202271

文献信息

• Direct Imidation to Construct 1<i>H</i>-Benzo[<i>d</i>]imidazole through Pd^II-Catalyzed CH Activation Promoted by Thiourea
  作者：Qing Xiao、Wen-Hua Wang、Gang Liu、Fan-Ke Meng、Jia-Hua Chen、Zhen Yang、Zhang-Jie Shi

  DOI：10.1002/chem.200900154

  日期：2009.7.27

  method to construct 1H‐benzo[d]imidazole was developed by means of PdII‐catalyzed intramolecular CH activation starting from easily available N‐phenylbenzimidamide (see scheme). The detailed mechanism studies indicated that a palladacycle monomer or dimer is the key intermediate for this transformation and thiourea was used for the first time to promote the efficiency of CH activation.

  通过Pd II催化的分子内CH活化作用，从容易获得的N －苯基苯甲酰胺开始（见方案），开发了一种新的直接构建1 H苯并[ d ]咪唑的方法。详细的机理研究表明，palladacycle单体或二聚体是该转化的关键中间体，硫脲首次用于提高CH活化效率。
• The Synthesis of Benzimidazole Derivatives in the Absence of Solvent and Catalyst
  作者：Chuanming Yu、Peng Guo、Can Jin、Weike Su

  DOI：10.3184/030823409x447763

  日期：2009.5

  Differently substituted benzimidazoles have been synthesised from o-phenylenediamine and arylaldehydes or arylmethylene-malononitriles absorbed on silica gel. The reaction was carried out by intermittent grinding or by a microwave-assisted technique under solvent- and catalyst-free conditions giving good yields of the products.

  在硅胶上吸收邻苯二胺和芳基醛或芳基亚甲基丙二腈合成了不同取代的苯并咪唑。反应是在无溶剂和催化剂的条件下，通过间歇研磨或微波辅助技术进行的，产物收率很高。
• Cu(I)-Catalyzed Synthesis of 2-Substituted Benzimidazoles from 2-Iodoanilines and Amides
  作者：Hua Yuan、Yongxin Chen、Jinli Song、Chunxia Chen、Baohua Chen

  DOI：10.1002/cjoc.201300429

  日期：2013.10

  A novel and efficient approach to the synthesis of 2‐substituted benzimidazoles has been developed via CuI/DMEDA‐catalyzed coupling reaction and post‐cyclization with glacial acetic acid from readily available 2‐iodoanilines and amides. This method is suitable for the construction of a variety of benzimidazoles in moderate to good yields under short reaction times.

  通过CuI / DMEDA催化的偶联反应，以及从容易获得的2-碘苯胺和酰胺中用冰醋酸进行后环化反应，已开发出一种新颖且有效的合成2-取代苯并咪唑的方法。该方法适用于在短反应时间内以中等到良好的产率构建各种苯并咪唑。
• Synthesis of benzimidazoles by copper-catalyzed aerobic oxidative domino reaction of 1,2-diaminoarenes and arylmethyl halides
  作者：Dezhi Qiu、Haidong Wei、Lihong Zhou、Qingle Zeng

  DOI：10.1002/aoc.3089

  日期：2014.2

  Arylmethyl halides are readily synthesized via halogenation from the basic raw materials, even in green processes. They are used to replace their downstream products to prepare medicinally important 2‐aryl benzimidazoles. CuBr‐catalyzed synthesis of 2‐aryl benzimidazoles from arylmethyl halides and 1,2‐diaminoarenes via a one‐pot domino reaction is developed. This new synthetic method is simple, practical

  芳基甲基卤化物很容易通过卤化反应从基本原料合成，即使在绿色工艺中也是如此。它们被用来替代其下游产品，以制备具有医学重要性的2-芳基苯并咪唑。通过一锅多米诺反应，开发了CuBr催化的由芳基甲基卤化物和1,2-二氨基芳烃合成2-芳基苯并咪唑的方法。这种新的合成方法简单，实用且节省成本，并且可以耐受各种官能团。提出了通过一锅四步法进行CuBr催化的好氧氧化多米诺反应的机理。版权所有©2013 John Wiley＆Sons，Ltd.
• Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C–H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-<i>a</i>]isoquinolines
  作者：Jinsong Peng、Guoning Shang、Chunxia Chen、Zhongshuo Miao、Bin Li

  DOI：10.1021/jo302471z

  日期：2013.2.1

  An efficient "one-pot" route for the synthesis of benzo[4,5]imidazo[2,1-a] isoquinolines has been developed via nucleophilic addition of 2-aryl benzimidazoles to alkynyl bromides and subsequent palladium-catalyzed intramolecular C-H vinylation.