4,5-bis[4-(diethylaminosulfonyl)phenoxy]phthalonitrile | 1201810-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-bis[4-(diethylaminosulfonyl)phenoxy]phthalonitrile
• 英文别名: 4-[4,5-dicyano-2-[4-(diethylsulfamoyl)phenoxy]phenoxy]-N,N-diethylbenzenesulfonamide
• CAS: 1201810-25-4
• 化学式: C₂₈H₃₀N₄O₆S₂
• 分子量: 582.701
• InChiKey: ZHLJDPZNXAHRMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-bis[4-(diethylaminosulfonyl)phenoxy]phthalonitrile 在 戊醇 、 magnesium 作用下， 以 辛醇 为溶剂， 反应 3.0h， 以50%的产率得到{2,3,9,10,16,17,23,24-octakis[4-(diethylaminosulfonyl)phenoxy]phthalocyaninato}magnesium(II)
  参考文献：
  名称：

  Synthesis of sulfonamide-substituted phthalocyanines

  摘要：

  The synthesis and characterization of new phthalocyanines bearing eight N-alkyl or N-aryl sulfonamide groups is described. The synthetic route involves the chorosulfonation of 4,5-diphenoxyphthalonitrile with chlorosulfonic acid and reaction of the resulting 4,5-bis(p-chlorosulfonylphenoxy)phthalonitrile with amines. The sulfonamide-substituted phthalonitriles are then cyclotetramerized to yield the title Compounds in good yields (50-83%). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.128
• 作为产物：
  描述：

  4,5-bis(4-chlorosulfonylphenoxy)phthalonitrile 、 二乙胺 以 乙腈 为溶剂， 以67%的产率得到4,5-bis[4-(diethylaminosulfonyl)phenoxy]phthalonitrile
  参考文献：
  名称：

  Synthesis of sulfonamide-substituted phthalocyanines

  摘要：

  The synthesis and characterization of new phthalocyanines bearing eight N-alkyl or N-aryl sulfonamide groups is described. The synthetic route involves the chorosulfonation of 4,5-diphenoxyphthalonitrile with chlorosulfonic acid and reaction of the resulting 4,5-bis(p-chlorosulfonylphenoxy)phthalonitrile with amines. The sulfonamide-substituted phthalonitriles are then cyclotetramerized to yield the title Compounds in good yields (50-83%). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.128

文献信息

• Synthesis and high ranked NLT properties of new sulfonamide-substituted indium phthalocyanines
  作者：Eliana F.A. Carvalho、Mário J.F. Calvete、José A.S. Cavaleiro、Danilo Dini、Moreno Meneghetti、Augusto C. Tomé

  DOI：10.1016/j.ica.2010.07.062

  日期：2010.11

  The synthesis and characterization of three new indium phthalocyanines bearing eight N-alkyl- or N-arylsulfonamide groups is described. The new compounds are 2,3,9,10,16,17,23,24-octakis[4-(4-methoxyphenylaminosulfonyl] phenoxy]phthalocyaninato}indium(III) chloride (7), 2,3,9,10,16,17,23,24-octakis[4-diethylaminosulfonyl)phenoxy]phthalocyaninato}indium(III) chloride (8) and 2,3,9,10,16,17, 23,24-octakis[4-didodecylaminosulfonyl)phenoxy]phthalocyaninato}indium(III) chloride (9), and were obtained in 23-49% yields. The precursors of phthalocyanines 7-9 are sulfonamide-substituted phthalo-nitriles that can be prepared by reacting 4,5-bis(4-chlorosulfonylphenoxy)phthalonitrile (3) with amines. The nonlinear transmission (NLT) of complexes 7-9 was determined at 532 nm using ns pulses. All three phthalocyanines behave as reverse saturable absorbers with increasing efficiency of optical limiting in the order 7<8<9. A comparative analysis of the NLT results is attempted in terms of the structural differences in 7-9. (C) 2010 Elsevier B.V. All rights reserved.