6'-methyl-3-(4-nitrophenyloxy)-2,2'-bipyrazine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6'-methyl-3-(4-nitrophenyloxy)-2,2'-bipyrazine
• 英文别名: 5-Methyl-3-(6-methylpyrazin-2-yl)-2-(4-nitrophenoxy)pyrazine
• 化学式: C₁₆H₁₃N₅O₃
• 分子量: 323.311
• InChiKey: NZVFQWJQLJXEPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-chloromethyl-6'-methyl-2,2'-bipyrazine 、 4-nitrophenol sodium salt 以 乙腈 为溶剂， 反应 48.0h， 以35%的产率得到6'-methyl-6-(4-nitrophenyloxymethyl)-2,2'-bipyrazine
  参考文献：
  名称：

  Synthesis and Experimental Electron Density of Bis(heterocyclic) Azines: The Case of 6,6′-Bis(chloromethyl)-2,2′-bipyrazine

  摘要：

  The synthesis and reactivity of mono- and bis(chloromethyl)-2,2'-bipyrazines toward nucleophiles are reported. The reactivity of the bipyrazine ring is explained in terms of allylic substitution and rearrangement mechanisms. A new family of monofunctionalized bipyrazine derivatives as molecular building blocks for supermolecules has been obtained, opening access to unsymmetrical ligands. The low-temperature crystallographic structure and the experimental electron density distribution of 6,6'-bis(chloromethyl)-2,2'-bipyrazine have been determined on the basis of high-resolution X-ray diffraction data. The electron density of the molecule has been accurately analyzed using the topological properties of its gradient and Laplacian features. The reactivity of these bidentate molecules in metal complexation is related to the shape of the atomic basins and may be explained in terms of a key/lock-type interaction. The results are compared with corresponding data for 2,2'-dimethyl-6,6'-diphenyl-4,4'-bipyrimidine.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1427::aid-ejoc1427>3.0.co;2-p

文献信息

• Synthesis and Experimental Electron Density of Bis(heterocyclic) Azines: The Case of 6,6′-Bis(chloromethyl)-2,2′-bipyrazine
  作者：Florence Bodar-Houillon、Youssef Elissami、Alain Marsura、Nour Eddine Ghermani、Enrique Espinosa、Nouzha Bouhmaida、Abdelmalek Thalal

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1427::aid-ejoc1427>3.0.co;2-p

  日期：1999.6

  The synthesis and reactivity of mono- and bis(chloromethyl)-2,2'-bipyrazines toward nucleophiles are reported. The reactivity of the bipyrazine ring is explained in terms of allylic substitution and rearrangement mechanisms. A new family of monofunctionalized bipyrazine derivatives as molecular building blocks for supermolecules has been obtained, opening access to unsymmetrical ligands. The low-temperature crystallographic structure and the experimental electron density distribution of 6,6'-bis(chloromethyl)-2,2'-bipyrazine have been determined on the basis of high-resolution X-ray diffraction data. The electron density of the molecule has been accurately analyzed using the topological properties of its gradient and Laplacian features. The reactivity of these bidentate molecules in metal complexation is related to the shape of the atomic basins and may be explained in terms of a key/lock-type interaction. The results are compared with corresponding data for 2,2'-dimethyl-6,6'-diphenyl-4,4'-bipyrimidine.