5-(1H-indol-3-yl)-3-(2,4,6-trimethoxyphenyl)pyrazine-2(1H)-one | 1447330-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(1H-indol-3-yl)-3-(2,4,6-trimethoxyphenyl)pyrazine-2(1H)-one
• 英文别名: 5-(1H-indol-3-yl)-3-(2,4,6-trimethoxyphenyl)-1H-pyrazin-2-one
• CAS: 1447330-90-6
• 化学式: C₂₁H₁₉N₃O₄
• 分子量: 377.4
• InChiKey: PEGLRWPDCZBRDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4,6-三甲氧基苯乙酮 在 吡啶 、 selenium(IV) oxide 、 ammonium acetate 、 N,N'-羰基二咪唑 作用下， 以 N-甲基吡咯烷酮 、 溶剂黄146 为溶剂， 反应 1.07h， 生成 5-(1H-indol-3-yl)-3-(2,4,6-trimethoxyphenyl)pyrazine-2(1H)-one
  参考文献：
  名称：

  Effective synthesis of 3,5-diaryl-(1H)-pyrazin-2-ones via microwave mediated ring closure

  摘要：

  In this study we report on a flexible straight forward synthesis toward novel 3,5-diaryl-(1H)-pyrazin-2-ones. Our synthetic strategy involved an acyclic di-keto derivative as key intermediate. The final pyrazin-2-one ring closure reaction was yield-optimized by using a microwave mediated procedure and ammoniumacetate as nitrogen source. Our method is a suitable alternative to palladium-catalyzed coupling reactions for the 3,5-diaryl decoration of the (1H)-pyrazin-2-one scaffold. Since the (1H)-pyrazin-2-ones is present as scaffold in a number of biologically active compounds the reported synthetic platform is a useful approach to generate a set of highly diverse 3,5-diaryl-(1H)-pyrazin-2-one compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.095

文献信息

• Effective synthesis of 3,5-diaryl-(1H)-pyrazin-2-ones via microwave mediated ring closure
  作者：Eugen Johannes、Rebecca Horbert、Joachim Schlosser、Dorian Schmidt、Christian Peifer

  DOI：10.1016/j.tetlet.2013.05.095

  日期：2013.7

  In this study we report on a flexible straight forward synthesis toward novel 3,5-diaryl-(1H)-pyrazin-2-ones. Our synthetic strategy involved an acyclic di-keto derivative as key intermediate. The final pyrazin-2-one ring closure reaction was yield-optimized by using a microwave mediated procedure and ammoniumacetate as nitrogen source. Our method is a suitable alternative to palladium-catalyzed coupling reactions for the 3,5-diaryl decoration of the (1H)-pyrazin-2-one scaffold. Since the (1H)-pyrazin-2-ones is present as scaffold in a number of biologically active compounds the reported synthetic platform is a useful approach to generate a set of highly diverse 3,5-diaryl-(1H)-pyrazin-2-one compounds. (C) 2013 Elsevier Ltd. All rights reserved.