4-[2-(bis(2-hydroxyethyl)amino)ethoxy]phthalonitrile | 1422446-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-(bis(2-hydroxyethyl)amino)ethoxy]phthalonitrile
• CAS: 1422446-08-9
• 化学式: C₁₄H₁₇N₃O₃
• 分子量: 275.307
• InChiKey: CYEVKETWYGPBAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  100.51
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[2-(bis(2-hydroxyethyl)amino)ethoxy]phthalonitrile 、 苯硼酸 以 乙酸乙酯 为溶剂， 反应 24.0h， 以73%的产率得到4-(2-(2-phenyl-1,3,6,2-dioxazaborocan-6-yl)ethoxy)phthalonitrile
  参考文献：
  名称：

  Different phenylboronic acid azaester formation modes in a substituted zinc phthalocyanine and its precursor

  摘要：

  With the aim of preparing a novel Zn phthalocyanine bearing four phenylboronic azaester substituents at peripheral positions, 4(2-(bis(2-hydroxyethypamino)ethoxy]phthalonitrile (2) was synthesized by the aromatic nucleophilic substitution reaction of 4-nitrophthalonitrile with triethanolamine. 2,9(10),16(17),23(24)-Tetrakis-[2-(bis( hydroxyethyl)amino)ethoxy]-phthalocyaninatozinc (II) (4) was prepared from the cyclotetramerization of dinitrile 2 in the presence of anhydrous zinc(II) acetate by microwave irradiation. Alternatively, treatment of 2 with phenylboronic acid yielded the phenylboronic azaester (3), namely 4-(2-(2-phenyl-1,3,6,2-dioxazaborocan-6-ypethoxy)phthalonitrile. Treatment of phthalocyanine 4 with phenylboronic acid in a mixture of DMSO/toluene (20/1, v/v) afforded the desired phthalocyanine 5. The novel compounds were characterized by elemental analyses, IR, UV-Vis, H-1, C-13 and B-11 NMR spectra. The B-11 NMR data indicated that the boron atom of phthalonitrile 3 is in the tetra-coordinated state with the formation of a coordinative N-B bond (closed form), while in the case of phthalocyanine 5, the open conformer possessing a tricoordinated B atom is favoured. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.11.044
• 作为产物：
  描述：

  三乙醇胺 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 以58%的产率得到4-[2-(bis(2-hydroxyethyl)amino)ethoxy]phthalonitrile
  参考文献：
  名称：

  Different phenylboronic acid azaester formation modes in a substituted zinc phthalocyanine and its precursor

  摘要：

  With the aim of preparing a novel Zn phthalocyanine bearing four phenylboronic azaester substituents at peripheral positions, 4(2-(bis(2-hydroxyethypamino)ethoxy]phthalonitrile (2) was synthesized by the aromatic nucleophilic substitution reaction of 4-nitrophthalonitrile with triethanolamine. 2,9(10),16(17),23(24)-Tetrakis-[2-(bis( hydroxyethyl)amino)ethoxy]-phthalocyaninatozinc (II) (4) was prepared from the cyclotetramerization of dinitrile 2 in the presence of anhydrous zinc(II) acetate by microwave irradiation. Alternatively, treatment of 2 with phenylboronic acid yielded the phenylboronic azaester (3), namely 4-(2-(2-phenyl-1,3,6,2-dioxazaborocan-6-ypethoxy)phthalonitrile. Treatment of phthalocyanine 4 with phenylboronic acid in a mixture of DMSO/toluene (20/1, v/v) afforded the desired phthalocyanine 5. The novel compounds were characterized by elemental analyses, IR, UV-Vis, H-1, C-13 and B-11 NMR spectra. The B-11 NMR data indicated that the boron atom of phthalonitrile 3 is in the tetra-coordinated state with the formation of a coordinative N-B bond (closed form), while in the case of phthalocyanine 5, the open conformer possessing a tricoordinated B atom is favoured. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.11.044