5,6-bis(4-(hydroxymethyl)phenoxy)pyrazine-2,3-dicarbonitrile | 1238353-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-bis(4-(hydroxymethyl)phenoxy)pyrazine-2,3-dicarbonitrile
• 英文别名: 5,6-Bis[4-(hydroxymethyl)phenoxy]pyrazine-2,3-dicarbonitrile；5,6-bis[4-(hydroxymethyl)phenoxy]pyrazine-2,3-dicarbonitrile
• CAS: 1238353-41-7
• 化学式: C₂₀H₁₄N₄O₄
• 分子量: 374.356
• InChiKey: SBCFHUJNGODVHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,6-bis(4-(hydroxymethyl)phenoxy)pyrazine-2,3-dicarbonitrile 在 zinc chloride * 2 quinoline 作用下， 反应 0.08h， 以44%的产率得到2,3,9,10,16,17,23,24-octakis(4-(hydroxymethyl)phenoxy)-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：

  对羟基苯甲醇 、 5,6-二氯-2,3-二氰基吡嗪 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到5,6-bis(4-(hydroxymethyl)phenoxy)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

文献信息

• Synthesis of Unsymmetrical Alkyloxy/Aryloxy-azaphthalocyanines Based on a Transetherification Reaction
  作者：Veronika Novakova、Miroslav Miletin、Kamil Kopecky、Šárka Franzová、Petr Zimcik

  DOI：10.1002/ejoc.201100689

  日期：2011.10

  found to be suitable for the isolation of unsymmetrical alkyloxy/aryloxy-AzaPcs. Undesired transetherification with alkoxides, which is common with these types of compounds, was considered to be an advantage in this approach, and an unsymmetrical AzaPc was isolated in 10 % yield. An analysis of the transetherification process is also described. Unsymmetrical zinc(II) and magnesium(II) AzaPcs showed excellent

  描述了一种导致在外围带有一个芳氧基和七个丁氧基取代基的不对称氮杂酞菁 (AzaPcs) 的方法。测试了几种环四聚方法，包括金属盐在熔体/溶液中的模板效应和 Linstead 方法，但发现只有一种方法适用于不对称烷氧基/芳氧基-AzaPcs 的分离。与这些类型的化合物常见的与醇盐的不希望的转醚化被认为是这种方法的优势，并且以 10% 的产率分离了不对称的 AzaPc。还描述了转醚化过程的分析。不对称的锌 (II) 和镁 (II) AzaPcs 显示出优异的光谱特性（λmax = 620 nm；ϵ = 1.5–2.2 × 105 dm3mol–1 cm–1）以及有希望的单线态氧（ΦΔ = 0.44 和 0.26，分别）和荧光量子产率（分别为 ΦF = 0.50 和 0.65）。无金属导数（λmax = 603 和 640 nm；ϵ = 0.80 和 1.2 × 105 dm3 mol–1 cm–1）以不同的方式耗散能量，并且
• The synthesis, photochemical and photophysical properties of zinc aryloxy- and alkyloxy azaphthalocyanines
  作者：Veronika Novakova、Petr Zimcik、Miroslav Miletin、Petr Vůjtěch、Šárka Franzová

  DOI：10.1016/j.dyepig.2010.03.023

  日期：2010.10

  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.