1-(4-bromophenyl)-2-(2-methyl-1H-imidazol-1-yl)ethanone | 749160-94-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-bromophenyl)-2-(2-methyl-1H-imidazol-1-yl)ethanone
• 英文别名: 1-(4-bromophenyl)-2-(2-methylimidazol-1-yl)ethanone
• CAS: 749160-94-9
• 化学式: C₁₂H₁₁BrN₂O
• 分子量: 279.136
• InChiKey: HIRBXIFVUXDAPG-UHFFFAOYSA-N

物化性质

• 熔点：
  143-146 °C(Solv: benzene (71-43-2))
• 沸点：
  456.9±30.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-(4-bromophenyl)-2-(2-methyl-1H-imidazol-1-yl)ethanone 、 3-bromo-3-(4-methoxyphenyl)acrylaldehyde 在 potassium carbonate 、 cobalt(II) aceylacetonate 、 三环己基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以62%的产率得到(4-bromophenyl)(8-(4-methoxyphenyl)-3-methylimidazo[1,5-a]pyridin-5-yl)methanone
  参考文献：
  名称：

  钴催化串联一锅法合成多取代咪唑并[1,5-a]吡啶和咪唑并[1,5-a]异喹啉

  摘要：

  开发了一种高效的钴催化串联一锅法合成多取代的咪唑并[1,5 - a ]-N-杂芳烃。该方法涉及 Knoevenagel 缩合，然后是钴催化的直接烯基化，以一锅方式得到所需的多取代咪唑并[1,5- a ]吡啶和咪唑并[1,5 - a ]异喹啉。这种方法表现出广泛的底物范围，提供中等至良好（39-74%）的产量，并且可以放大到克级。

  DOI：

  10.1039/d2ob00526c
• 作为产物：
  描述：

  2-甲基咪唑 、 2,4'-二溴苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 1-(4-bromophenyl)-2-(2-methyl-1H-imidazol-1-yl)ethanone
  参考文献：
  名称：

  Novel inhibitors of nitric oxide synthase with antioxidant properties

  摘要：

  We previously described a series of imidazole-based inhibitors substituted at N-1 with an arylethanone chain as interesting inhibitors of neuronal nitric oxide synthase (nNOS), endowed with good selectivity vs endothelial nitric oxide synthase (eNOS). As a follow up of these studies, several analogs characterized by the presence of substituted imidazoles or other mono or bicyclic nitrogen-containing heterocycles instead of simple imidazole were synthesized, and their biological evaluation as in vitro inhibitors of both nNOS and eNOS is described herein. Most of these compounds showed improved nNOS and eNOS inhibitory activity with respect to reference inhibitors. Selected compounds were also tested to analyze their antioxidant properties. Some of them displayed good capacity to scavenge free radicals and ability to reduce lipid peroxidation. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.002

文献信息

• Novel inhibitors of nitric oxide synthase with antioxidant properties
  作者：Loredana Salerno、Maria N. Modica、Giuseppe Romeo、Valeria Pittalà、Maria A. Siracusa、Maria E. Amato、Rosaria Acquaviva、Claudia Di Giacomo、Valeria Sorrenti

  DOI：10.1016/j.ejmech.2012.01.002

  日期：2012.3

  We previously described a series of imidazole-based inhibitors substituted at N-1 with an arylethanone chain as interesting inhibitors of neuronal nitric oxide synthase (nNOS), endowed with good selectivity vs endothelial nitric oxide synthase (eNOS). As a follow up of these studies, several analogs characterized by the presence of substituted imidazoles or other mono or bicyclic nitrogen-containing heterocycles instead of simple imidazole were synthesized, and their biological evaluation as in vitro inhibitors of both nNOS and eNOS is described herein. Most of these compounds showed improved nNOS and eNOS inhibitory activity with respect to reference inhibitors. Selected compounds were also tested to analyze their antioxidant properties. Some of them displayed good capacity to scavenge free radicals and ability to reduce lipid peroxidation. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Cobalt-catalyzed tandem one-pot synthesis of polysubstituted imidazo[1,5-<i>a</i>]pyridines and imidazo[1,5-<i>a</i>]isoquinolines
  作者：Neha Meena、Shiv Dhiman、Krishnan Rangan、Anil Kumar

  DOI：10.1039/d2ob00526c

  日期：——

  An efficient cobalt-catalyzed tandem one-pot method has been developed for the synthesis of polysubstituted imidazo[1,5-a]-N-heteroaromatics. The method involves Knoevenagel condensation followed by cobalt-catalyzed direct alkenylation to give the desired polysubstituted imidazo[1,5-a]pyridines and imidazo[1,5-a]isoquinolines in a one-pot manner. This method exhibits a broad substrate scope, provides

  开发了一种高效的钴催化串联一锅法合成多取代的咪唑并[1,5 - a ]-N-杂芳烃。该方法涉及 Knoevenagel 缩合，然后是钴催化的直接烯基化，以一锅方式得到所需的多取代咪唑并[1,5- a ]吡啶和咪唑并[1,5 - a ]异喹啉。这种方法表现出广泛的底物范围，提供中等至良好（39-74%）的产量，并且可以放大到克级。