2-(3-nitrophenyl)-1-methyl-1H-benzimidazole | 3718-02-3

• 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-nitrophenyl)-1-methyl-1H-benzimidazole
• 英文别名: 1-methyl-2-(3'-nitrophenyl)benzimidazole；1-methyl-2-(3-nitrophenyl)-1H-benzo[d]imidazole；1-methyl-2-(3-nitro-phenyl)-1H-benzoimidazole；1-methyl-2-(3-nitrophenyl)-1H-1,3-benzodiazole；1-methyl-2-(3-nitrophenyl)benzimidazole
• CAS: 3718-02-3
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: ZUSUIYNBLDOINK-UHFFFAOYSA-N

物化性质

• 熔点：
  151-154 °C
• 沸点：
  454.4±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)-1-methyl-1H-benzimidazole 在 palladium on activated charcoal 哌啶 、 sodium hydroxide 、 氢气 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 7.0h， 生成 N-[3-(1-methyl-1H-benzimidazol-2-yl)-phenyl]-2-phenylthio-acetamide
  参考文献：
  名称：

  Synthesis and antimicrobial activities of some new benzimidazole derivatives

  摘要：

  Some benzimidazolylbenzamides were synthesized and their antimicrobial activities against Staphylococcus aureus, Streptococcus faecalis, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Candida albicans evaluated. It was shown that the compound 14 exhibited the best activity against B. subtilis, P. aeruginosa and C. albicans.

  DOI：

  10.1016/s0014-827x(03)00190-3
• 作为产物：
  描述：

  1-甲基-2-苯基苯并咪唑 在 十二羰基三钌 、 copper(II) nitrate trihydrate 、 oxone||potassium monopersulfate triple salt 、 四丁基醋酸铵 、 silver trifluoroacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以42%的产率得到2-(3-nitrophenyl)-1-methyl-1H-benzimidazole
  参考文献：
  名称：

  通过 Ru3(CO)12 催化的邻位金属化策略对芳烃进行间位选择性 CAr-H 硝化

  摘要：

  描述了过渡金属催化芳烃间位选择性 CAr-H 硝化的第一个例子。以Ru3(CO)12为催化剂，以Cu(NO3)2·3H2O为硝基源，以间位选择性专门硝化了具有多种N-杂环或肟基作为导向基团的广谱芳烃。机理研究表明，形成了一种新的 18e-八面体钌物质作为关键的邻位 CAr-H 金属化中间体，这可能是随后的间选择性亲电芳香取代 (SEAr) 的原因。此外，这种方法为许多有用的药物分子的原子/分步经济合成提供了快速通道策略。

  DOI：

  10.1021/jacs.6b03402

文献信息

• 一种金属配合物、合成方法及其在有机电致发光器件中的应用
  申请人：长春海谱润斯科技有限公司

  公开号：CN107353309A

  公开（公告）日：2017-11-17

  本发明公开了一种金属配合物、合成方法及其在有机电致发光器件中的应用，所述金属配合物的通式为：其中，R1选自取代或未取代的C1～C30的烷基、取代或未取代的C1～C60烷氧基、取代或非取代C6～C60芳基、取代或非取代C5～C60杂环基、取代或非取代C5～C60的稠环基；L选自O、S、取代或未取代的胺基、取代或未取代的硅烷基；M选自Pt、Pd、Ir、R或Au；A选自取代或非取代C6～C60芳基、取代或非取代C5～C60杂环基、取代或非取代C5～C60的稠环基。本发明所述金属配合物制备的有机电致发光器件可有限解决现有技术中有机光电材料发光效率低、驱动电压较高、使用寿命短等发光性能差的技术问题。
• Design and Synthesis of 2-Arylbenzimidazoles and Evaluation of Their Inhibitory Effect against <i>Chlamydia pneumoniae</i>
  作者：Leena Keurulainen、Olli Salin、Antti Siiskonen、Jan Marco Kern、Joni Alvesalo、Paula Kiuru、Matthias Maass、Jari Yli-Kauhaluoma、Pia Vuorela

  DOI：10.1021/jm1008083

  日期：2010.11.11

  Chlamydia pneumoniae is an intracellular bacterium that responds poorly to antibiotic treatment. Insufficient antibiotic usage leads to chronic infection, which is linked to disease processes of asthma, atherosclerosis, and Alzheimer's disease. The Chlamydia research lacks genetic tools exploited by other antimicrobial research, and thus other approaches to drug discovery must be applied. A set of 2-arylbenzimidazoles was designed based on our earlier findings, and 33 derivatives were synthesized. Derivatives were assayed against C. pneumoniae strain CWL-029 in an acute infection model using TR-FIA method at a concentration of 10 mu M, and the effects of the derivatives on the host cell viability were evaluated at the same concentration. Fourteen compounds showed at least 80% inhibition, with only minor changes in host cell viability. Nine most potential compounds were evaluated using immunofluorescence microscopy on two different strains of C. pneumoniae CWL-029 and CV-6. The N-[3-(1H-benzimidazol-2-yl)phenyl]-3-methylbenzamide (42) had minimal inhibitory concentration (MIC) of 10 mu M against CWL-029 and 6.3 mu M against the clinical strain CV-6. This study shows the high antichlamydial potential of 2-arylbenzimidazoles, which also seem to have good characteristics for lead compounds.
• A Keggin heteropoly acid as an efficient catalyst for an expeditious, one-pot synthesis of 1-methyl-2-(hetero)arylbenzimidazoles
  作者：Manas Chakrabarty、Ajanta Mukherji、Ratna Mukherjee、Shiho Arima、Yoshihiro Harigaya

  DOI：10.1016/j.tetlet.2007.05.144

  日期：2007.7

  The Keggin heteropoly acid, silicotungstic acid, H4SiW12O40, has been demonstrated to be highly efficient for an expeditious, one-pot synthesis of 1-methyl-2-(hetero)arylbenzimidazoles from N-methyl-1,2-phenylenediamine and (hetero)aryl aldehydes in ethyl acetate at room temperature. The catalyst works equally well for N-phenyl-1,2-phenylenediamine. (c) 2007 Elsevier Ltd. All rights reserved.
• Meta-Selective C_Ar–H Nitration of Arenes through a Ru₃(CO)₁₂-Catalyzed Ortho-Metalation Strategy
  作者：Zhoulong Fan、Jiabin Ni、Ao Zhang

  DOI：10.1021/jacs.6b03402

  日期：2016.7.13

  as the catalyst and Cu(NO3)2·3H2O as the nitro source, a wide spectrum of arenes bearing diversified N-heterocycles or oximido as the directing groups were nitrated with meta-selectivity exclusively. Mechanism studies have demonstrated the formation of a new 18e-octahedral ruthenium species as a key ortho-CAr-H metalated intermediate, which may be responsible for the subsequent meta-selective electrophilic

  描述了过渡金属催化芳烃间位选择性 CAr-H 硝化的第一个例子。以Ru3(CO)12为催化剂，以Cu(NO3)2·3H2O为硝基源，以间位选择性专门硝化了具有多种N-杂环或肟基作为导向基团的广谱芳烃。机理研究表明，形成了一种新的 18e-八面体钌物质作为关键的邻位 CAr-H 金属化中间体，这可能是随后的间选择性亲电芳香取代 (SEAr) 的原因。此外，这种方法为许多有用的药物分子的原子/分步经济合成提供了快速通道策略。
• Synthesis and antimicrobial activities of some new benzimidazole derivatives
  作者：Gülgün Ayhan-Kılcıgil、Nurten Altanlar

  DOI：10.1016/s0014-827x(03)00190-3

  日期：2003.12

  Some benzimidazolylbenzamides were synthesized and their antimicrobial activities against Staphylococcus aureus, Streptococcus faecalis, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Candida albicans evaluated. It was shown that the compound 14 exhibited the best activity against B. subtilis, P. aeruginosa and C. albicans.