4-(5-methoxy-1H-1,3-benzodiazol-2-yl)phenol | 1159707-22-8

• 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: 4-(5-methoxy-1H-1,3-benzodiazol-2-yl)phenol
• 英文别名: 4-(6-methoxy-1H-benzimidazol-2-yl)phenol
• CAS: 1159707-22-8
• 化学式: C₁₄H₁₂N₂O₂
• mdl: MFCD20947048
• 分子量: 240.261
• InChiKey: DADMNEOAKBEOHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  492.3±51.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  58.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-methoxy-1H-1,3-benzodiazol-2-yl)phenol 、 1-溴-3-氯丙烷 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以62%的产率得到2-[4-(3-chloropropoxy)phenyl]-6-methoxy-1H-benzimidazole
  参考文献：
  名称：

  选择性酚烷基化可改善2-芳基苯并咪唑H 4受体配体的合成

  摘要：

  研究了在游离苯并咪唑NH存在下苯酚OH的烷基化反应，发现该反应高度依赖于苯并咪唑和苯酚环的取代。我们对2-芳基苯并咪唑H 4受体配体的原始合成方法进行了改进，从而提高了收率，并易于分离最终产物。

  DOI：

  10.1016/j.tetlet.2009.03.033
• 作为产物：
  描述：

  对羟基苯甲醛 、 2-硝基-4-甲氧基苯胺 在 sodium dithionite 作用下， 以 甲醇 为溶剂， 反应 0.6h， 生成 4-(5-methoxy-1H-1,3-benzodiazol-2-yl)phenol
  参考文献：
  名称：

  Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives

  摘要：

  A series of 2-arylbenzimidazole derivatives (3a-3p and 4a-4i) were synthesized and evaluated as potential antioxidant and antimicrobial agents. Their antioxidant properties were evaluated by various in vitro assays including hydroxyl radical (HO center dot) scavenging, superoxide radical anion (O-2(center dot)) scavenging, 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical scavenging, and ferric reducing antioxidant power. Results demonstrated that compounds with hydroxyl group at the 5-position of benzimidazole ring had a comparable or better antioxidant activity in comparison to standard antioxidant tert-butylhydroquinone (TBHQ). Markedly, compound 4h that showed the highest HO center dot scavenging activity (EC50 = 46 mu M) in vitro had a significant reduction of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced intracellular oxidative stress and H2O2-induced cell death. In addition, these compounds showed moderate to good inhibitory activity against Staphylococcus aureus selectively at noncytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.004

文献信息

• Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives
  作者：Binhua Zhou、Baojian Li、Wei Yi、Xianzhang Bu、Lin Ma

  DOI：10.1016/j.bmcl.2013.05.004

  日期：2013.7

  A series of 2-arylbenzimidazole derivatives (3a-3p and 4a-4i) were synthesized and evaluated as potential antioxidant and antimicrobial agents. Their antioxidant properties were evaluated by various in vitro assays including hydroxyl radical (HO center dot) scavenging, superoxide radical anion (O-2(center dot)) scavenging, 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical scavenging, and ferric reducing antioxidant power. Results demonstrated that compounds with hydroxyl group at the 5-position of benzimidazole ring had a comparable or better antioxidant activity in comparison to standard antioxidant tert-butylhydroquinone (TBHQ). Markedly, compound 4h that showed the highest HO center dot scavenging activity (EC50 = 46 mu M) in vitro had a significant reduction of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced intracellular oxidative stress and H2O2-induced cell death. In addition, these compounds showed moderate to good inhibitory activity against Staphylococcus aureus selectively at noncytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.
• Selective phenol alkylation for an improved synthesis of 2-arylbenzimidazole H4 receptor ligands
  作者：Brad M. Savall、Jill R. Fontimayor、James P. Edwards

  DOI：10.1016/j.tetlet.2009.03.033

  日期：2009.5

  free benzimidazole NH was investigated and found to be highly dependent on the substitution of the benzimidazole and phenol rings. The modification of our original synthesis of 2-arylbenzimidazole H4 receptor ligands has resulted in improved yields and ease of isolation of final products.

  研究了在游离苯并咪唑NH存在下苯酚OH的烷基化反应，发现该反应高度依赖于苯并咪唑和苯酚环的取代。我们对2-芳基苯并咪唑H 4受体配体的原始合成方法进行了改进，从而提高了收率，并易于分离最终产物。