5,6-dimethyl-2-(p-tolyl)-1H-benzo[d]imidazole | 70151-41-6

• 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: 5,6-dimethyl-2-(p-tolyl)-1H-benzo[d]imidazole
• 英文别名: 5,6-dimethyl-2-(4-methylphenyl)-1H-benzimidazole
• CAS: 70151-41-6
• 化学式: C₁₆H₁₆N₂
• mdl: MFCD11912388
• 分子量: 236.316
• InChiKey: JDJSPQLJMCMXAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 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：

  5,6-dimethyl-2-(p-tolyl)-1H-benzo[d]imidazole 在 4-二甲氨基吡啶 、 potassium acetate 、 fac-Ir(ppy)₃ 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 3,5,9,10-tetramethyl-5-(2,2,2-trifluoroethyl)benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one
  参考文献：
  名称：

  Redox-Neutral Photocatalytic Radical Cascade Cyclization for the Synthesis of CH₂CN/CF₂COOEt/CF₃-Containing Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-One Derivatives

  摘要：

  A novel method for the synthesis of benzo[4,5]imidazo[2,1-a]isoquinolin derivatives via visible-light-induced radical cascade cyclization is described. By using N-methacryloyl-2-phenylbenzoimidazoles and diverse radical precursors, various benzo[4,5]imidazo[2,1-a]isoquinolin derivatives containing CH2CN/CF2COOEt/CF3 can be formed in good to excellent yields under mild reaction conditions. This method exhibits good functional group tolerance and a wide range of substrate scope.

  DOI：

  10.1021/acs.joc.0c01688
• 作为产物：
  描述：

  4-甲基苯甲酸酐 、 4，5-二甲基-1，2-苯二胺 生成 5,6-dimethyl-2-(p-tolyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Jerchel et al., Justus Liebigs Annalen der Chemie, 1952, vol. 575, p. 162,167

  摘要：

  DOI：

文献信息

• Copper(I)-Catalyzed Regioselective Amination of <i>N</i>-Aryl Imines Using TMSN₃ and TBHP: A Route to Substituted Benzimidazoles
  作者：Devulapally Mahesh、Pradeep Sadhu、Tharmalingam Punniyamurthy

  DOI：10.1021/jo502574u

  日期：2015.2.6

  efficient copper-catalyzed amination of N-aryl imines is described. This one-pot, multicomponent reaction, in which imine acts as a directing group by chelating to the metal center, affords a potential route for the transformation of the commercial aryl amines, aldehydes, and azides into valuable benzimidazole structural units with wide substrate scope and diversity. The synthetic and mechanistic aspects

  描述了新颖和有效的铜催化的N-芳基亚胺的胺化。这种单锅多组分反应（其中亚胺通过与金属中心的螯合而充当导向基团）提供了潜在的途径，可将商业化的芳基胺，醛和叠氮化物转化为有价值的苯并咪唑结构单元，具有广泛的底物范围和多样性。提出了综合和机制方面。
• Simple and Efficient Method for the Synthesis of Benzimidazole Derivatives using Monoammonium Salt of 12‐Tungstophosphoric Acid
  作者：B. Y. Giri、B. L. A. Prabavathi Devi、K. N. Gangadhar、K. Vijaya Lakshmi、R. B. N. Prasad、N. Lingaiah、P. S. Sai Prasad

  DOI：10.1080/00397910701410681

  日期：2007.7

  Abstract Benzimidazoles have been synthesized in very good yield from o‐phenylenediamine and aromatic aldehydes in the presence of monoammonium salt of 12‐tungstophosphoric acid [(NH4)H2PW12O40], an efficient heterogeneous catalyst. This catalyst has the advantages of simple workup procedure, water insolubility, and good activity with high yield for the synthesis of benzimidazole derivatives.

  摘要 在 12-钨磷酸单铵盐 [(NH4)H2PW12O40]（一种高效的多相催化剂）存在下，由邻苯二胺和芳香醛以非常好的收率合成了苯并咪唑。该催化剂具有后处理简单、不溶于水、合成苯并咪唑衍生物活性好、收率高等优点。
• Boosting charge separation in conjugated microporous polymers <i>via</i> fluorination for enhancing photocatalysis
  作者：Penghao Sun、Peigen Wang、Dong Yan、Qian Liu、Weijie Zhang、Jiyong Deng、Qingquan Liu

  DOI：10.1039/d2cy01294d

  日期：——

  and promote charge separation in CMPs by selectively employing carbazole as the donor and fluorinated precursors as the acceptor, respectively. As a result, a series of fluorinated CbzCMP-n (n = 10–12) featuring π-conjugates of the donor (D)–acceptor (A) structure is obtained, in which both their effective charge separation and transfer and broadly visible light absorbance are facilitated. The fluorinated

  共轭微孔聚合物（CMPs）由于其易于功能化、高表面积和孔隙率以及可调节的带隙，已成为用于光催化有氧氧化的有前景的多相光催化剂。然而，由于快速的电荷复合和电荷分离不足，它们的光催化效率远低于预期。在此，通过选择性地使用咔唑作为供体和氟化前体作为受体，开发了一种氟化策略来抑制电荷复合并促进CMP中的电荷分离。结果，一系列氟化 CbzCMP- n ( n= 10-12) 获得了具有供体 (D)-受体 (A) 结构的 π 共轭体，其中促进了它们的有效电荷分离和转移以及宽可见光吸收。与不含氟化的对应物 CbzCMP-10 相比，氟化的 CbzCMP-11 和 CbzCMP-12 显着提高了光催化效率，苯并咪唑的光催化结构和硫化物的氧化证明了这一点。这种氟化策略有助于更好地平衡电子和空穴迁移速率、抑制电荷复合以及扩大 CMP 作为无金属光催化剂在各种有机转化转化中的前景。
• Rh(III)‐Catalyzed Oxidative Annulation of 2‐Aryl‐1 <i>H</i> ‐benzo[ <i>d</i> ]imidazoles with 1,4‐Quinones through C−H Activation
  作者：G. Siva Sankaram、B. Sridhar、B. V. Subba Reddy

  DOI：10.1002/ejoc.202201113

  日期：2022.12.19

  A new method has been developed for the synthesis of benzo[4,5]imidazo[1,2-f]phenanthridine-1,4-dione scaffolds by means of transition metal catalyzed oxidative annulation of 2-aryl-1H-benzo[d]imidazole with 1,4-quinones.

  通过过渡金属催化的 2-aryl-1 H -benzo[的氧化环化，开发了一种合成苯并 [4,5] 咪唑并 [1,2- f ] 菲啶 - 1,4- 二酮支架的新方法。 d ]咪唑与 1,4-醌。
• Efficient Synthesis of Benzimidazole and Quinoline Derivatives Catalyzed by Functionalized Amidato Ruthenium Complexes in Water <i>via</i> Acceptorless Dehydrogenative Coupling Strategy
  作者：Xin Liu、Wen‐Zhe Dong、Yining Liu、Wei‐Yu Shao、Yang Li、Xiaoqiang Yu、Yuichiro Himeda、Wan‐Hui Wang、Ming Bao

  DOI：10.1002/cctc.202300817

  日期：2023.8.21

  Versatile: A bifunctional amidato Ru catalyst was developed for highly efficient and selective synthesis of benzimidazole and quinoline derivatives in water via acceptorless dehydrogenative coupling strategy. Mechanistic studies revealed the significant synergetic effect of the ligand and Ru center in catalyzing dehydrogenation of the alcohols.dehydrogenative couplingaqueous phaseruthenium complexbenzimidazolequinoline

  绿色多功能：开发了一种双功能酰胺基钌催化剂，通过无受体脱氢偶联策略，在水中高效选择性合成苯并咪唑和喹啉衍生物。机理研究揭示了配体和Ru中心在催化醇脱氢过程中具有显着的协同作用。脱氢偶联水相钌配合物苯并咪唑喹啉