1-(naphthalen-1-ylmethyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole | 1173269-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-1-ylmethyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole
• 英文别名: 1-(Naphthalen-1-ylmethyl)-2-pyridin-2-ylbenzimidazole
• CAS: 1173269-33-4
• 化学式: C₂₃H₁₇N₃
• 分子量: 335.408
• InChiKey: ALWNFNGDBLGBLO-UHFFFAOYSA-N

物化性质

• 沸点：
  594.0±52.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [RhCl2(p-cymene)]2 、 1-(naphthalen-1-ylmethyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole 以 乙醇 为溶剂， 反应 24.0h， 以98%的产率得到[RuCl(p-cymene)(L6)]Cl
  参考文献：
  名称：

  Heteroleptic ruthenium(II) complexes of 2-(2-pyridyl)benzimidazoles: A study of catalytic efficiency towards transfer hydrogenation of acetophenone

  摘要：

  Six ruthenium(II) complexes ([RuCl2(p-cymene)(L1-6)], SD1-6, (L1-6: bidentate pyridyl-benzimidazole ligands)) were synthesized from [RuCl2(p-cymene)](2) dimer and bidentate pyridyl-benzimidazole ligands. The compounds were characterized by elemental analysis, IR, UV-Vis, NMR and X-ray diffraction. The synthesized Ru(II) complexes (SDI-6) were tested as catalysts for the catalytic transfer hydrogenation (CH) of acetophenone to secondary alcohols in the presence of KOH using 2-propanol as a hydrogen source at 82 degrees C. All complexes were active catalysts for TM of acetophenone with good yields under mild conditions (after 15 min, yields of up to 91%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.10.012
• 作为产物：
  描述：

  2-(2-吡啶)-苯并咪唑 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以68%的产率得到1-(naphthalen-1-ylmethyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Heteroleptic ruthenium(II) complexes of 2-(2-pyridyl)benzimidazoles: A study of catalytic efficiency towards transfer hydrogenation of acetophenone

  摘要：

  Six ruthenium(II) complexes ([RuCl2(p-cymene)(L1-6)], SD1-6, (L1-6: bidentate pyridyl-benzimidazole ligands)) were synthesized from [RuCl2(p-cymene)](2) dimer and bidentate pyridyl-benzimidazole ligands. The compounds were characterized by elemental analysis, IR, UV-Vis, NMR and X-ray diffraction. The synthesized Ru(II) complexes (SDI-6) were tested as catalysts for the catalytic transfer hydrogenation (CH) of acetophenone to secondary alcohols in the presence of KOH using 2-propanol as a hydrogen source at 82 degrees C. All complexes were active catalysts for TM of acetophenone with good yields under mild conditions (after 15 min, yields of up to 91%). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.10.012

文献信息

• Design, Synthesis, Binding and Docking-Based 3D-QSAR Studies of 2-Pyridylbenzimidazoles—A New Family of High Affinity CB1 Cannabinoid Ligands
  作者：Jaime Mella-Raipán、Carlos Lagos、Gonzalo Recabarren-Gajardo、Christian Espinosa-Bustos、Javier Romero-Parra、Hernán Pessoa-Mahana、Patricio Iturriaga-Vásquez、Carlos Pessoa-Mahana

  DOI：10.3390/molecules18043972

  日期：——

  A series of novel 2-pyridylbenzimidazole derivatives was rationally designed and synthesized based on our previous studies on benzimidazole 14, a CB1 agonist used as a template for optimization. In the present series, 21 compounds displayed high affinities with Ki values in the nanomolar range. JM-39 (compound 39) was the most active of the series (KiCB1 = 0.53 nM), while compounds 31 and 44 exhibited similar affinities to WIN 55212-2. CoMFA analysis was performed based on the biological data obtained and resulted in a statistically significant CoMFA model with high predictive value (q2 = 0.710, r2 = 0.998, r2pred = 0.823).

  基于我们之前对用于优化模板的CB1激动剂苯并咪唑14的研究，我们合理设计并合成了一系列新型2-吡啶基苯并咪唑衍生物。在本系列化合物中，21种化合物显示出高亲和力，Ki值在纳摩尔范围内。JM-39（化合物39）是该系列中活性最高的（KiCB1 = 0.53 nM），而化合物31和44显示出与WIN 55212-2相似的亲和力。基于获得的生物学数据进行了CoMFA分析，并得到了一个统计学上显著且具有高度预测价值的CoMFA模型（q2 = 0.710，r2 = 0.998，r2pred = 0.823）。