2-((4-nitrophenoxy)methyl)-5-bromo-1H-benzimidazole | 1160557-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((4-nitrophenoxy)methyl)-5-bromo-1H-benzimidazole
• 英文别名: 2-((4-nitrophenoxy)methyl)-5-bromobenzimidazole
• CAS: 1160557-15-2
• 化学式: C₁₄H₁₀BrN₃O₃
• 分子量: 348.156
• InChiKey: FKQAIIOLQOMTBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((4-nitrophenoxy)methyl)-5-bromo-1H-benzimidazole 在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 以78%的产率得到4-((5(6)-bromo-1H-benzoimidazol-2-l)methoxy)benzenamine
  参考文献：
  名称：

  Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles as possible antimicrobial and antitubercular agents

  摘要：

  In this Letter, we report the structure activity relationship (SAR) studies on series of positional isomers of 5(6)-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles derivatives 7(a-j) and 8(a j) synthesized in good yields and characterized by H-1 NMR, C-13 NMR and mass spectral analyses. The crystal structure of 7a was evidenced by X-ray diffraction study. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, (Gram-positive), Escherichia coli and Klebsiella pneumoniae (Gram-negative), antifungal activity against Candida albicans, Aspergillus flavus and Rhizopus sp. and antitubercular activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis, Mycobacterium fortuitum and MDR-TB strains. The synthesized compounds displayed interesting antimicrobial activity. The compounds 7b, 7e and 7h displayed significant activity against Mycobacterium tuberculosis H37Rv strain. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.072
• 作为产物：
  描述：

  (4-硝基苯氧基)乙酸乙酯 在 四丁基氯化铵 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 2-((4-nitrophenoxy)methyl)-5-bromo-1H-benzimidazole
  参考文献：
  名称：

  Design and synthesis of positional isomers of 5 and 6-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles as possible antimicrobial and antitubercular agents

  摘要：

  In this Letter, we report the structure activity relationship (SAR) studies on series of positional isomers of 5(6)-bromo-1-[(phenyl)sulfonyl]-2-[(4-nitrophenoxy)methyl]-1H-benzimidazoles derivatives 7(a-j) and 8(a j) synthesized in good yields and characterized by H-1 NMR, C-13 NMR and mass spectral analyses. The crystal structure of 7a was evidenced by X-ray diffraction study. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, (Gram-positive), Escherichia coli and Klebsiella pneumoniae (Gram-negative), antifungal activity against Candida albicans, Aspergillus flavus and Rhizopus sp. and antitubercular activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis, Mycobacterium fortuitum and MDR-TB strains. The synthesized compounds displayed interesting antimicrobial activity. The compounds 7b, 7e and 7h displayed significant activity against Mycobacterium tuberculosis H37Rv strain. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.072

文献信息

• Tetra Butyl Ammonium Chloride Catalyzed Synthesis of Substituted Benzimidazoles under Microwave Conditions
  作者：Ranjith. P. Karuvalam、M. Siji、N. Divia.、Karickal. R. Haridas

  DOI：10.5012/jkcs.2010.54.5.589

  日期：2010.10.20

  TBACl (10 mol %) 를 촉매로 사용하여 치환된benzimidazoles을 합성하는 간단하고 효율적인 합성방을 개발하였다. TBACl (10 mol %) was found to be a useful catalyst for the synthesis of substituted benzimidazoles. The method was proved to be simple, convenient and the product was isolated with good yield.

  使用TBACl (10 mol %)作为催化剂，开发了一种简单而高效的合成方法，用于合成取代的苯并咪唑。该方法被证明简单便捷，产物的收率良好。
• TRIMETHYLSILYL CHLORIDE CATALYZED SYNTHESIS OF SUBSTITUTED BENZIMIDAZOLES USING TWO PHASE SYSTEM UNDER MICROWAVE CONDITIONS, AND THEIR ANTIMICROBIAL STUDIES
  作者：RANJITH. P KARUVALAM、KARICKAL. R HARIDAS、SUCHETHA. N SHETTY

  DOI：10.4067/s0717-97072012000200014

  日期：——

  A convenient method using TMSCl (20 mol %) and microwave-induced technique for the synthesis of various benzimidazole is described. This has reduced the reaction time drastically as well as improved the yield when compared to conventional heating. The synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities against four strains each. Preliminary results indicated that, compounds 3e, 31, 3g, 3k, 3m, 3n and 3o demonstrated very good antimicrobial activity, comparable to the first line standard drugs. The most effective compounds have exhibited activity at MIC of 6.25 mu g/mL.