2-苄基-3H-苯并咪唑-5-醇 | 131336-23-7

• 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-苄基-3H-苯并咪唑-5-醇
• 英文名称: 2-benzyl-5-hydroxybenzimidazole
• 英文别名: 2-benzyl-5(6)-hydroxybenzimidazole；1H-Benzimidazol-5-ol, 2-(phenylmethyl)-；2-benzyl-3H-benzimidazol-5-ol
• CAS: 131336-23-7
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: IBUGFPGBFUVOCW-UHFFFAOYSA-N

物化性质

• 沸点：
  523.0±33.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苄基-3H-苯并咪唑-5-醇 在 硫酸 作用下， 以65.8%的产率得到2-benzyl-5-hydroxy-1H-benzimidazole-4-sulfonic acid
  参考文献：
  名称：

  Study of the electrophilic substitution of alkyl-, aryl-, and aralkyl-5(6)-hydroxybenzimidazoles

  摘要：

  A series of new 4-sulfo-5(6)-hydroxybenzimidazoles was obtained including monodi-, and trinitro derivatives of 2-phenyl- and 2-benzyl-5-hydroxybenzimidazoles. Aromatic groups at C2, in contrast to alkyl groups, enhance the reactivity of the benzimidazole system in electrophilic substitution.

  DOI：

  10.1007/bf00961508
• 作为产物：
  描述：

  N-(2-氨基-4-乙氧基苯基)乙酰胺 在 氢溴酸 作用下， 反应 26.0h， 生成 2-苄基-3H-苯并咪唑-5-醇
  参考文献：
  名称：

  Basicity and structure of 5-hydroxybenzimidazoles in nitromethane

  摘要：

  Examination of the acid-base properties of 5-hydroxybenzimidazoles has shown them to exist in nitromethane as the 5-hydroxy-tautomers. Substituents in the 2-position have a predominantly inductive effect on the basicity of the 3-nitrogen, rationalized as in other nitrogen heterocycles by the proximity of the substituents to the reaction center.

  DOI：

  10.1007/bf00869526

文献信息

• A novel series of benzimidazole NR2B-selective NMDA receptor antagonists
  作者：David J. Davies、Matthew Crowe、Nolwenn Lucas、Joanna Quinn、David D. Miller、Sara Pritchard、David Grose、Ezio Bettini、Novella Calcinaghi、Caterina Virginio、Lee Abberley、Paul Goldsmith、Anton D. Michel、Iain P. Chessell、James N.C. Kew、Neil D. Miller、Martin J. Gunthorpe

  DOI：10.1016/j.bmcl.2012.01.108

  日期：2012.4

  A series of novel benzimidazoles are discussed as NR2B-selective N-methyl-d-aspartate (NMDA) receptor antagonists. High throughput screening (HTS) efforts identified a number of potent and selective NR2B antagonists such as 1. Exploration of the substituents around the core of this template identified a number of compounds with high potency for NR2B (pIC50 >7) and good selectivity against the NR2A

  一系列新颖的苯并咪唑类的作为NR2B选择性讨论Ñ甲基d天冬氨酸（NMDA）受体拮抗剂。高通量筛选（HTS）的努力确定了许多有效的和选择性的NR2B拮抗剂，例如1。通过对模板核心周围的取代基进行探索，发现了许多对NR2B具有高效力的化合物（pIC 50 > 7），并且对FL2R-Ca 2+和放射性配体结合的NR2A亚基具有良好的选择性（pIC 50 <4.3）。学习。这些药物为开发包括慢性疼痛，神经退行性疾病，偏头痛和重度抑郁症在内的多种神经系统疾病提供了潜力。
• KUZNETSOV, YU. V.;STOLYAROVA, L. G.;LEZINA, V. P.;SMIRNOV, L. D., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 1888-1892
  作者：KUZNETSOV, YU. V.、STOLYAROVA, L. G.、LEZINA, V. P.、SMIRNOV, L. D.

  DOI：——

  日期：——
• Study of the electrophilic substitution of alkyl-, aryl-, and aralkyl-5(6)-hydroxybenzimidazoles
  作者：Yu. V. Kuznetsov、L. G. Stolyarova、V. P. Lezina、L. D. Smirnov

  DOI：10.1007/bf00961508

  日期：1990.8

  A series of new 4-sulfo-5(6)-hydroxybenzimidazoles was obtained including monodi-, and trinitro derivatives of 2-phenyl- and 2-benzyl-5-hydroxybenzimidazoles. Aromatic groups at C2, in contrast to alkyl groups, enhance the reactivity of the benzimidazole system in electrophilic substitution.
• Basicity and structure of 5-hydroxybenzimidazoles in nitromethane
  作者：B. A. Korolev、L. A. Osmolovskaya、Yu. V. Kuznetsov、L. G. Stolyarova、L. D. Smirnov

  DOI：10.1007/bf00869526

  日期：1992.2

  Examination of the acid-base properties of 5-hydroxybenzimidazoles has shown them to exist in nitromethane as the 5-hydroxy-tautomers. Substituents in the 2-position have a predominantly inductive effect on the basicity of the 3-nitrogen, rationalized as in other nitrogen heterocycles by the proximity of the substituents to the reaction center.