1-ethyl-6-(2-iodo-2-phenyl-vinyl)-5-thiophen-3-yl-1,6-dihydropyrazine-2,3-dicarbonitrile | 1192308-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 1-ethyl-6-(2-iodo-2-phenyl-vinyl)-5-thiophen-3-yl-1,6-dihydropyrazine-2,3-dicarbonitrile
• 英文别名: 1-ethyl-2-[(E)-2-iodo-2-phenylethenyl]-3-thiophen-3-yl-2H-pyrazine-5,6-dicarbonitrile
• CAS: 1192308-44-3
• 化学式: C₂₀H₁₅IN₄S
• 分子量: 470.336
• InChiKey: QZLGAVVZWFREST-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-dicyano-5-(3-thienyl)-1-ethylpyrazinium tetrafluoroborate 、 苯乙炔 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.58h， 以19%的产率得到1-ethyl-6-(2-iodo-2-phenyl-vinyl)-5-thiophen-3-yl-1,6-dihydropyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  Reactions of Radicals Generated from 1-Ethyl-1,4-diazinium-salts: Addition to the C-C Triple Bond versus Dimerization

  摘要：

  Radical species generated from 5-aryl-substituted 1-ethyl-2,3-dicyano-1,4-diazinium salts by action of sodium iodide undergo dimerization into [2,2']bipyrazinyl derivatives, as evidenced by NMR and X-ray crystallography data. The pyrazinyl radicals can also be involved into the addition reaction on the C-C triple bond, thus demonstrating a new synthetic route to modify the structure of pyrazines. The structures of E- and Z-isomers of 1-(1',2'-dihydropyrazinyl-2')-2-iodoethenes have been proved by H-1 and C-13 NMR spectroscopy and X-ray analysis.

  DOI：

  10.3987/com-09-11734