5,6-bis(octyloxy)pyrazine-2,3-dicarbonitrile | 1238353-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-bis(octyloxy)pyrazine-2,3-dicarbonitrile
• CAS: 1238353-34-8
• 化学式: C₂₂H₃₄N₄O₂
• 分子量: 386.538
• InChiKey: GVMQIECZEAUSAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  91.82
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,6-bis(octyloxy)pyrazine-2,3-dicarbonitrile 在 zinc chloride * 2 quinoline 作用下， 反应 1.0h， 以20%的产率得到2,3,9,10,16,17,23,24-octakis(octyloxy)-1,4,8,11,15,18,22,25-(octaaza)phthalocyanine zinc(II)
  参考文献：
  名称：

  The synthesis, photochemical and photophysical properties of zinc aryloxy- and alkyloxy azaphthalocyanines

  摘要：

  Octasubstituted zinc tetrapyrazinoporphyrazines bearing butyloxy, octyloxy, 2,6-diisopropylphenoxy and 4-(hydroxymethyl)phenoxy substituents were synthesized from the corresponding 5,6-disubstituted pyrazine-2,3-dicarbonitriles using Zn(quinoline)(2)Cl-2 in yields varying from 14 to 44%. The reaction procedure proved to be efficient for the synthesis of both alkyloxy- and aryloxy- substituted zinc tetrapyrazinoporphyrazines and did not require strictly anhydrous conditions. Optimal cyclotetramerization conditions were identified for each derivative, in terms of reaction temperature, as overheating cleaved the ether bond leaving a vacant OH group on the macrocycle. The photochemical and photophysical properties of the synthesized compounds were investigated in pyridine. Singlet oxygen quantum yields (Phi(Delta)) ranged from 0.49 to 0.61 and high fluorescence quantum yields (Phi(F)) of similar to 0.30 were observed for non-aggregated compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.03.023
• 作为产物：
  描述：

  辛醇 、 5,6-二氯-2,3-二氰基吡嗪 在 三乙胺 作用下， 以 辛醇 为溶剂， 反应 0.75h， 以51%的产率得到5,6-bis(octyloxy)pyrazine-2,3-dicarbonitrile
  参考文献：
  名称：

  The synthesis, photochemical and photophysical properties of zinc aryloxy- and alkyloxy azaphthalocyanines

  摘要：

  Octasubstituted zinc tetrapyrazinoporphyrazines bearing butyloxy, octyloxy, 2,6-diisopropylphenoxy and 4-(hydroxymethyl)phenoxy substituents were synthesized from the corresponding 5,6-disubstituted pyrazine-2,3-dicarbonitriles using Zn(quinoline)(2)Cl-2 in yields varying from 14 to 44%. The reaction procedure proved to be efficient for the synthesis of both alkyloxy- and aryloxy- substituted zinc tetrapyrazinoporphyrazines and did not require strictly anhydrous conditions. Optimal cyclotetramerization conditions were identified for each derivative, in terms of reaction temperature, as overheating cleaved the ether bond leaving a vacant OH group on the macrocycle. The photochemical and photophysical properties of the synthesized compounds were investigated in pyridine. Singlet oxygen quantum yields (Phi(Delta)) ranged from 0.49 to 0.61 and high fluorescence quantum yields (Phi(F)) of similar to 0.30 were observed for non-aggregated compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.03.023