(2-methyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone | 92568-81-5

• 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-methyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone
• 英文别名: 1H-Benzimidazole, 1-benzoyl-2-methyl-；(2-methylbenzimidazol-1-yl)-phenylmethanone
• CAS: 92568-81-5
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: QKHRLROZDNYADQ-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C(Solv: methanol (67-56-1))
• 沸点：
  423.6±28.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-methyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone 生成 1-(acetyl-benzoyl-amino)-2-benzoylamino-benzene
  参考文献：
  名称：

  Wolff, Justus Liebigs Annalen der Chemie, 1913, vol. 399, p. 311

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基苯并咪唑 、 苯甲醛 在 二叔丁基过氧化物 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以96%的产率得到(2-methyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles

  摘要：

  A novel and direct cross-dehydrogenative coupling (CDC) between benzimidazoles with aldehydes promoted by di-tert-butyl peroxide (DTBP) was developed. The reactions generated the corresponding N-acylbenzimidazoles in good yields under metal-free conditions. This method has broad substrate scope and high efficiency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.009

文献信息

• Synthesis and Antimicrobial Activity of Some Benzimidazole and 2-Methylbenzimidazole Derivatives
  作者：P. Jain、M. Tiwari

  DOI：10.14233/ajchem.2017.20328

  日期：——

  In the present work, benzimidazole and 2-methylbenzimidazole derivatives were synthesized and evaluated for antimicrobial activity against Escherichia coli (Gram-negative bacteria), Staphylococcus aureus (Gram-positive bacteria) and Candida albicans (fungal stain). The structure of the synthesized compounds was confirmed by FTIR, 1H NMR and mass spectroscopy. Antimicrobial activity of all the synthesized compounds was carried out by Broth dilution method to determine MIC value. Compounds P2, P7 and P10 showed better antibacterial activity against Escherichia coli as compared to benzimidazole, 2-methylbenzimidazole and ampicillin. Compounds P8 and P12 showed better antibacterial activity against Staphylococcus aureus as compared to benzimidazole, 2-methylmenzimidazole and ampicillin. Compound P2 and P9 showed better antifungal activity against Candida albicans as compared to benzimidazole, 2-methylbenzimidazole and griseofulvin.

  本研究合成了苯并咪唑和 2-甲基苯并咪唑衍生物，并评估了它们对大肠杆菌（革兰氏阴性菌）、金黄色葡萄球菌（革兰氏阳性菌）和白色念珠菌（真菌染色）的抗菌活性。傅立叶变换红外光谱、1H NMR 和质谱证实了合成化合物的结构。所有合成化合物的抗菌活性均采用肉汤稀释法测定 MIC 值。与苯并咪唑、2-甲基苯并咪唑和氨苄西林相比，化合物 P2、P7 和 P10 对大肠杆菌具有更好的抗菌活性。与苯并咪唑、2-甲基苯并咪唑和氨苄西林相比，化合物 P8 和 P12 对金黄色葡萄球菌具有更好的抗菌活性。与苯并咪唑、2-甲基苯并咪唑和格列齐芬相比，化合物 P2 和 P9 对白色念珠菌具有更好的抗真菌活性。
• Kumar, P. Raja, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1273 - 1274
  作者：Kumar, P. Raja

  DOI：——

  日期：——
• DENNIS, T. J.;KUMAR, K. AKSHAYA;SRIMANNARAYANA, G., ORG. PREP. AND PROCED. INT., 1984, 16, N 3-4, 286-289
  作者：DENNIS, T. J.、KUMAR, K. AKSHAYA、SRIMANNARAYANA, G.

  DOI：——

  日期：——
• KUMAR, P. RAJA, INDIAN J. CHEM., 25,(1986) N 12, 1273-1274
  作者：KUMAR, P. RAJA

  DOI：——

  日期：——
• Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles
  作者：Lin Yu、Min Wang、Lei Wang

  DOI：10.1016/j.tet.2014.07.009

  日期：2014.9

  A novel and direct cross-dehydrogenative coupling (CDC) between benzimidazoles with aldehydes promoted by di-tert-butyl peroxide (DTBP) was developed. The reactions generated the corresponding N-acylbenzimidazoles in good yields under metal-free conditions. This method has broad substrate scope and high efficiency. (C) 2014 Elsevier Ltd. All rights reserved.