3-methylamino-6-(2-phenylethynyl)pyrazine-2-carboxylic acid | 647826-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-methylamino-6-(2-phenylethynyl)pyrazine-2-carboxylic acid
• 英文别名: Pyrazinecarboxamide, N-methyl-3-(methylamino)-6-(phenylethynyl)-；N-methyl-3-(methylamino)-6-(2-phenylethynyl)pyrazine-2-carboxamide
• CAS: 647826-48-0
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: OMBRTELPQGTSMF-UHFFFAOYSA-N

物化性质

• 沸点：
  469.5±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-chloro-1,3-dimethylpteridine-2,4(1H,3H)-dione 在 tris-(dibenzylideneacetone)dipalladium(0) 哌啶 、 copper(l) iodide 、 bis(pyridine)silver(I) permanganate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168002.0h， 生成 3-methylamino-6-(2-phenylethynyl)pyrazine-2-carboxylic acid
  参考文献：
  名称：

  摘要：

  Sonogashira cross-coupling of 6-chloro-1,3-dimethyllumazine with terminal alkynes gave 6-alkynyl derivatives in good yields. Oxidative amination of the latter with primary alkylamines was accompanied by the pyrrole-ring closure to form 1-R'-2-R-6,8-dimethylpyrrolo[3,2-g]pteridine-5,7(6H,8H)-diones. The addition of bromine to 6-alkynyllumazines afforded the corresponding dibromoalkenes whose treatment with sodium trithiocarbonate gave rise to 2-R-6,8-dimethyltliieno[3,2-g]pteridine-5,7(6H,8H)-diones. The latter compounds are close analogs of the metabolite of molybdenum cofactor (molybdopterine).

  DOI：

  10.1023/a:1024891530684

文献信息

• ——
  作者：A. V. Gulevskaya、Dang Van Shee、A. F. Pozharskii

  DOI：10.1023/a:1024891530684

  日期：——

  Sonogashira cross-coupling of 6-chloro-1,3-dimethyllumazine with terminal alkynes gave 6-alkynyl derivatives in good yields. Oxidative amination of the latter with primary alkylamines was accompanied by the pyrrole-ring closure to form 1-R'-2-R-6,8-dimethylpyrrolo[3,2-g]pteridine-5,7(6H,8H)-diones. The addition of bromine to 6-alkynyllumazines afforded the corresponding dibromoalkenes whose treatment with sodium trithiocarbonate gave rise to 2-R-6,8-dimethyltliieno[3,2-g]pteridine-5,7(6H,8H)-diones. The latter compounds are close analogs of the metabolite of molybdenum cofactor (molybdopterine).