2-(2-羟基苯基)-5-甲基-1H-苯并咪唑 | 6266-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(2-羟基苯基)-5-甲基-1H-苯并咪唑
• 英文名称: 2-(5(6)-methyl-1H-benzoimidazol-2-yl)-phenol
• 英文别名: 2-(6-methyl-1H-benzimidazol-2-yl)phenol
• CAS: 6266-09-7
• 化学式: C₁₄H₁₂N₂O
• mdl: MFCD01836518
• 分子量: 224.262
• InChiKey: RENIIFGMUKZWHA-UHFFFAOYSA-N

物化性质

• 熔点：
  240.2-242.1 °C
• 沸点：
  453.8±47.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2-羟基苯基)-5-甲基-1H-苯并咪唑 、 壬酸 在 PPA 作用下， 反应 6.0h， 以13%的产率得到1-壬烷酮,1-[4-羟基-3-(5-甲基-1H-苯并咪唑-2-基)苯基]-
  参考文献：
  名称：

  Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases

  摘要：

  A series of 16 substituted 2-(2-hydroxphenyl)benzimidazoles was synthesized and evaluated in vitro for antibacterial activity against bacteria associated with periodontal diseases. Several compounds demonstrated a high level of activity, in tube dilution assay, against Actinomycetes viscosus and Bacteriodes gingivalis. These results indicate that several of these compounds may serve as topical antibacterial agents for the control of acute marginal inflammatory gingivitis and periodontitis.

  DOI：

  10.1021/jm00384a035
• 作为产物：
  描述：

  水杨酰胺 在 四氢吡咯 、 三氯氧磷 、 三氯化磷 作用下， 以 乙腈 、 苯 为溶剂， 反应 23.0h， 生成 2-(2-羟基苯基)-5-甲基-1H-苯并咪唑
  参考文献：
  名称：

  Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases

  摘要：

  A series of 16 substituted 2-(2-hydroxphenyl)benzimidazoles was synthesized and evaluated in vitro for antibacterial activity against bacteria associated with periodontal diseases. Several compounds demonstrated a high level of activity, in tube dilution assay, against Actinomycetes viscosus and Bacteriodes gingivalis. These results indicate that several of these compounds may serve as topical antibacterial agents for the control of acute marginal inflammatory gingivitis and periodontitis.

  DOI：

  10.1021/jm00384a035

文献信息

• A Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles
  作者：Kiumars Bahrami、Mohammad Khodaei、Iman Kavianinia

  DOI：10.1055/s-2007-965878

  日期：2007.2

  A simple and efficient procedure for the synthesis of substituted benzimidazoles through a one-pot condensation of o-phenylenediamines with aryl aldehydes in the presence of H2O2/HCl system in acetonitrile at room temperature is described. Short reaction time, large-scale synthesis, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure.

  本文介绍了一种简单高效的一锅法合成取代苯并咪唑的工艺：在室温下，以乙腈为溶剂，在H2O2/HCl体系存在下，将邻苯二胺与芳醛进行缩合反应。该工艺的主要优点包括反应时间短、规模化合成、产物分离简便快捷以及产率优异。
• 1H-benzimidazole derivatives as butyrylcholinesterase inhibitors: synthesis and molecular modeling studies
  作者：Gunes Coban、Luca Carlino、Ayse Hande Tarikogullari、Sülünay Parlar、Görkem Sarıkaya、Vildan Alptüzün、Ayşe Selcen Alpan、Hasan Semih Güneş、Erçin Erciyas

  DOI：10.1007/s00044-016-1648-1

  日期：2016.9

  A series of N-2-[2-(1H-benzimidazole-2-yl)phenoxy]ethyl} substituted amine derivatives were synthesized and tested for their cholinesterase inhibitor activity. Acetylcholinesterase and butyrylcholinesterase inhibitor activities were evaluated in vitro by using Ellman’s method. According to the activity results, all of the compounds displayed moderate acetylcholinesterase inhibitory activity and most

  合成了一系列的N- 2- [2-（1 H-苯并咪唑-2-基）苯氧基]乙基}取代的胺衍生物，并测试了它们的胆碱酯酶抑制剂活性。使用Ellman方法在体外评估乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂的活性。根据活性结果，所有化合物均表现出中等的乙酰胆碱酯酶抑制活性，大多数化合物表现出显着的丁酰胆碱酯酶抑制活性。化合物3d是该系列中活性最高的化合物，也是选择性的丁酰胆碱酯酶抑制剂。还进行了分子对接研究和分子动力学模拟。
• Aroyl[bis(4-hydroxycoumarin-3-yl)]methanes in reactions with 1,2-diaminobenzenes
  作者：N. N. Kolos、L. L. Gozalishvili、F. G. Yaremenko、O. V. Shishkin、S. V. Shishkina、I. S. Konovalova

  DOI：10.1007/s11172-007-0359-7

  日期：2007.11

  The reaction of aroyl[bis(4-hydroxycoumarin-3-yl)]methanes with 1,2-phenylenediamines in PriOH is accompanied by the recyclization to 8-R-or 7-R-4-(2-hydroxyphenyl)-1,5-benzodiazepin-2-ones, whereas the reaction with o-phenylenediamine and its 4-methyl-substituted derivatives in MeOH produces organic ionic salts of the bis-coumarin anion with monoprotonated o-phenylenediamine as the cation.

  芳酰[双(4-hydroxycoumarin-3-yl)]甲烷与1,2-苯二胺在异丙醇中的反应伴随着回环生成8-R或7-R-4-(2-羟基苯基)-1,5-苯二氮杂卓-2-酮，而与邻苯二胺及其4-甲基取代衍生物在甲醇中反应则生成有机离子盐，包含双香豆素阴离子和单质子化的邻苯二胺作为阳离子。
• Preparation, characterization, DFT calculations and ethylene oligomerization studies of iron(II) complexes bearing 2-(1H-benzimidazol-2-yl)-phenol derivatives
  作者：Marzieh Haghverdi、Azadeh Tadjarodi、Naeimeh Bahri-Laleh、Mehdi Nekoomanesh Haghighi

  DOI：10.1080/00958972.2018.1446527

  日期：2018.4.18

  Abstract Five 2-(1H-benzimidazol-2-yl)-phenol derivatives including 1H (HL1), 5-chloro-(HL2), 5-methyl-(HL3), 5,6-dichloro-(HL4), and 5,6-dimethyl-(HL5) were synthesized by the reaction of their corresponding benzene-1,2-diamine precursors and 2-hydroxybenzaldehyde which subsequently was employed in complexation with Fe(II) to prepare complexes C1–C5, respectively. Indeed, in all complexes, the ligands

  摘要 五种 2-(1H-苯并咪唑-2-基)-苯酚衍生物，包括 1H (HL1)、5-氯-(HL2)、5-甲基-(HL3)、5,6-二氯-(HL4) 和 5 ,6-二甲基-(HL5) 是通过其相应的苯-1,2-二胺前体和 2-羟基苯甲醛反应合成的，随后将其与 Fe(II) 络合以分别制备配合物 C1-C5。实际上，在所有配合物中，配体分别通过苯并咪唑部分和苯酚环的 C=N 氮和羟基氧原子配位为双齿。通过 FTIR、UV-vis、1H-和 13C-NMR 光谱、ICP 和元素分析（C、H 和 N）对化合物进行表征。这些化合物的纯度由熔点 (mp) 和 TLC 确定。合成的配体和配合物通过 Gaussian09 软件在 B3LYP/TZVP 理论水平进行几何优化，并在分析化合物的 IR 数据时实现了令人满意的理论-实验一致性。针对乙烯反应性研究了铁 (II) 配合物的催化行为。在用二乙基氯化铝 (Et2AlCl)
• DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media
  作者：Vikash Kumar、Dipratn G. Khandare、Amrita Chatterjee、Mainak Banerjee

  DOI：10.1016/j.tetlet.2013.07.147

  日期：2013.10

  synthetic method has been developed for the facile synthesis of 2-substituted benzimidazoles in organized aqueous media in the presence of a surfactant (viz. DBSA) as catalyst and I2 as co-catalyst. The method described has the advantages of operational simplicity, excellent yields, high chemoselectivity, and clean and green reaction profile.

  已经开发出一种有效的合成方法，用于在表面活性剂（即DBSA）作为催化剂和I 2作为助催化剂的存在下，在有组织的水性介质中轻松合成2-取代的苯并咪唑。所描述的方法的优点是操作简单，产率高，化学选择性高，反应曲线干净绿色。