5-(pyridin-3-yloxy)-6-methylpyrazine-2,3-dicarbonitrile | 1190850-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(pyridin-3-yloxy)-6-methylpyrazine-2,3-dicarbonitrile
• 英文别名: 5-Methyl-6-pyridin-3-yloxypyrazine-2,3-dicarbonitrile
• CAS: 1190850-61-3
• 化学式: C₁₂H₇N₅O
• 分子量: 237.22
• InChiKey: WWRJKNFTLALNFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  95.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Zn(quinoline)2Cl2 、 5-(pyridin-3-yloxy)-6-methylpyrazine-2,3-dicarbonitrile 以 neat (no solvent) 为溶剂， 以39%的产率得到[tetra(pyridin-3-yloxy)-tetramethyl(octazaphthalocyaninato)]zinc(II)
  参考文献：
  名称：

  Zinc azaphthalocyanines with pyridin-3-yloxy peripheral substituents

  摘要：

  Phthalocyanines (Pc), which are peripherally substituted with pyridin-3-yloxy groups, have shown promise as sensitizers for photodynamic cancer therapy (PDT). Some aza-analogues (AzaPc) are reported here. Four monomers were synthesized, i.e. 5.6-di(pyridin-3-yloxy)pyrazine-2,3-dicarbonitrile, and three pyrazine-2,3-dicarbonitriles, substituted with pyridin-3-yloxy- in combination with H, Me and Ph groups. Cyclotetramerizations of these monomers with the reagent Zn(quinoline)(2)Cl(2) yielded the targeted ZnAzaPcs in 20-40% yields.The cyclotetramerizations were accompanied, and apparently initiated, by complexation between zinc(II) and the pyridin-3-yloxy groups attached to the pyrazine-dicarbonitriles. Two such zinc(II) complexes were isolated and characterized. Identifications of all new substances were primarily based on NMR spectra, where the pulse techniques COSY, NOESY, HSQC and HMBC were applied. Molecular ions of the ZnAzaPcs were determined by mass spectrometry (MALDI-TOF). The UV-Vis spectra of these macrocycles were as expected, with Q-band absorptions at 630-650 nm and molar extinction coefficients, epsilon, 70 000-100 000. Eight peripheral pyridin-3-yloxy groups induced a small blue shift of the Q-band, from 636 nm for unsubstituted ZnAzaPc, to 630 mn, whereas a red shifted Q-band at 650 nm resulted from the combination of phenyl and pyridin-3-yloxy substituents. Improved solubilities were observed for the unsymmetrical ZnAzaPcs compared to octa(pyridin-3-yloxy)ZnAzaPc. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.05.060