4-pent-4-ynyloxy-phthalonitrile | 1430800-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-pent-4-ynyloxy-phthalonitrile
• 英文别名: 4-pent-4-ynyloxyphthalonitrile；4-Pent-4-ynoxybenzene-1,2-dicarbonitrile；4-pent-4-ynoxybenzene-1,2-dicarbonitrile
• CAS: 1430800-85-3
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: UHBRWOBTNMNREM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-叔丁基邻苯二甲腈 、 4-pent-4-ynyloxy-phthalonitrile 、 zinc diacetate 以 戊醇 为溶剂， 反应 24.0h， 以22.7%的产率得到9,16,23-tri-tert-butyl-2-(pent-4-ynoxy)phthalocyaninatozinc(II)
  参考文献：
  名称：

  Synthesis and characterization of terminalalkynyl-substituted unsymmetrical zinc phthalocyanine conjugated with well-defined polymers

  摘要：

  Synthesis of unsymmetrically terminalalkynyl substituted zinc (II) phthalocyanine (ZnPc) through an efficient statistical condensation reaction with the unprotected phthalonitrile (2) is reported for the first time. Isolated ZnPc bearing one terminalalkynyl group is a good precursor for Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction which is classified under the term "click chemistry". This was approved by the successful click reaction between ZnPc and azide end-functional well-defined polymers obtained by atom transfer radical polymerization (ATRP), and consecutive azidation of corresponding bromo end-functional polymers. The click-reaction efficiencies for the formation of Pc-end functional poly(tert-butyl acrylate) (PtBA), and polystyrene (PS) have been found to be 75, 93% respectively. Functionalization of ZnPc with PS increased the chemical stability of the complex but decreased the electrochemical reversibility during redox reactions. In-situ electrocolorimetric measurements of the complexes allowed the quantification of color coordinates of the each electrogenerated anionic and cationic redox species. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.07.018
• 作为产物：
  描述：

  4-戊炔-1-醇 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以69.49%的产率得到4-pent-4-ynyloxy-phthalonitrile
  参考文献：
  名称：

  通过点击反应合成新型四末端炔基取代的酞菁及其星形聚合物

  摘要：

  第一次，对称的四末端炔基取代的酞菁（Pcs）被聚合物官能化，即通过1,3-偶极环加成反应。为此目的，通过4-硝基邻苯二甲腈（1）和4-戊炔-1-醇（2）的亲核取代反应来制备4-戊-4-炔氧基-邻苯二甲腈（3）。靶2,9的（10）（17）的合成，16，23（24） -四终端炔基-取代的酞菁（4 - 6）用合理的产率通过一个直接cyclotetramerization反应中的乙酸锌存在下实现的，戊醇中的乙酸钴和/或DBU，无保护/脱保护。定义明确的叠氮基封端的聚苯乙烯（PS-N）之间的成功“点击”反应3）（7）或聚（丙烯酸叔丁酯）（P t BA-N 3）（8）和炔基封端的酞菁（4、5）产生四臂星形聚合物。通过1 H NMR，13 C NMR，FT-IR，UV-Vis，GPC和元素分析对前驱物和目标星形聚合物进行了全面表征。

  DOI：

  10.1016/j.dyepig.2013.02.014

文献信息

• Synthesis and characterization of novel tetra terminal alkynyl-substituted phthalocyanines and their star polymers via click reaction
  作者：Hatice Dinçer、Humeyra Mert、Betül Nur Şen、Aydan Dağ、Sinem Bayraktar

  DOI：10.1016/j.dyepig.2013.02.014

  日期：2013.8

  cobalt acetate, and/or DBU in pentanol without protection/deprotection. Successful ‘click’ reactions between well defined azido-terminated polystyrene (PS-N3) (7) or poly(tert-butyl acrylate) (PtBA-N3) (8) and alkynyl-terminated phthalocyanines (4, 5) yielded four arm star polymers. The precursors and the target star polymers were characterized comprehensively by 1H NMR, 13C NMR, FT-IR, UV–Vis, GPC and elemental

  第一次，对称的四末端炔基取代的酞菁（Pcs）被聚合物官能化，即通过1,3-偶极环加成反应。为此目的，通过4-硝基邻苯二甲腈（1）和4-戊炔-1-醇（2）的亲核取代反应来制备4-戊-4-炔氧基-邻苯二甲腈（3）。靶2,9的（10）（17）的合成，16，23（24） -四终端炔基-取代的酞菁（4 - 6）用合理的产率通过一个直接cyclotetramerization反应中的乙酸锌存在下实现的，戊醇中的乙酸钴和/或DBU，无保护/脱保护。定义明确的叠氮基封端的聚苯乙烯（PS-N）之间的成功“点击”反应3）（7）或聚（丙烯酸叔丁酯）（P t BA-N 3）（8）和炔基封端的酞菁（4、5）产生四臂星形聚合物。通过1 H NMR，13 C NMR，FT-IR，UV-Vis，GPC和元素分析对前驱物和目标星形聚合物进行了全面表征。
• Synthesis and characterization of terminalalkynyl-substituted unsymmetrical zinc phthalocyanine conjugated with well-defined polymers
  作者：Betül Nur Şen、Humeyra Mert、Hatice Dinçer、Atıf Koca

  DOI：10.1016/j.dyepig.2013.07.018

  日期：2014.1

  Synthesis of unsymmetrically terminalalkynyl substituted zinc (II) phthalocyanine (ZnPc) through an efficient statistical condensation reaction with the unprotected phthalonitrile (2) is reported for the first time. Isolated ZnPc bearing one terminalalkynyl group is a good precursor for Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction which is classified under the term "click chemistry". This was approved by the successful click reaction between ZnPc and azide end-functional well-defined polymers obtained by atom transfer radical polymerization (ATRP), and consecutive azidation of corresponding bromo end-functional polymers. The click-reaction efficiencies for the formation of Pc-end functional poly(tert-butyl acrylate) (PtBA), and polystyrene (PS) have been found to be 75, 93% respectively. Functionalization of ZnPc with PS increased the chemical stability of the complex but decreased the electrochemical reversibility during redox reactions. In-situ electrocolorimetric measurements of the complexes allowed the quantification of color coordinates of the each electrogenerated anionic and cationic redox species. (C) 2013 Elsevier Ltd. All rights reserved.