4-(4-pyridyloxy)phthalonitrile | 380896-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-pyridyloxy)phthalonitrile
• 英文别名: 4-Pyridin-4-yloxybenzene-1,2-dicarbonitrile
• CAS: 380896-89-9
• 化学式: C₁₃H₇N₃O
• 分子量: 221.218
• InChiKey: DQXFLOUMWDEYNV-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  427.4±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-pyridyloxy)phthalonitrile 在 氨 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以77%的产率得到5-(pyridine-4-oxy)-1H-isoindole-1,3(2H)-diimine
  参考文献：
  名称：

  酞菁钴配合物的合成，电化学和电催化活性-取代基对氧还原反应的影响

  摘要：

  摘要单（吡啶-4-氧基）-三（叔丁基）酞菁钴Co（II）（Pc1）和单（吡啶-4-氧基）-六（己基）酞菁邻苯二酚的合成，表征，电化学和电催化活性此处报道了Co（II）（Pc2）。对于循环伏安图上的两个络合物，观察到一个可逆和一个不可逆的氧化对和两个准可逆的还原对。酞菁钴衍生物（CoPcs）和多壁碳纳米管（MWCNT）复合材料（CoPcs / MWCNT）电极均涂在玻璃碳电极上，并用作氧还原反应（ORR）的电催化剂。复合表面的形态使用扫描电子显微镜（SEM）进行表征。使用旋转圆盘电极（RDE）获得的结果表明，在碱性介质中，分别对Pc1 / MWCNT和Pc2 / MWCNT杂化催化剂使用4e-和混合2e- – 4e- ORR机理观察到高催化活性。与CoPc环上的己基取代基相比，具有所需4e-机理的叔丁基取代基对复合电极的催化活性更有效。

  DOI：

  10.1016/j.poly.2018.06.018
• 作为产物：
  描述：

  4-羟基吡啶 、 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 120.0h， 以72.43%的产率得到4-(4-pyridyloxy)phthalonitrile
  参考文献：
  名称：

  一种基于阳离子酞菁钴（ii）和碳纳米管的逐层多层膜的用于检测亚硝酸盐和过氧化氢的电化学双功能传感器。

  摘要：

  作为重要的生物介质，准确检测亚硝酸盐（NO2--）和过氧化氢（H2O2）对于临床监测和诊断是理想的。本文中，将阳离子2,9,16,23-四[4-（N-甲基）吡啶氧基]酞菁钴（ii）（[TMPyPcCo] 4+）和酸处理的多壁碳纳米管（aCNT）交替自组装在玻碳电极（GCE）通过静电相互作用，导致[TMPyPcCo / aCNTs] n多层膜的3D松散且相互连接的组装。在[TMPyPcCo / aCNTs] n薄膜中，[TMPyPcCo] 4+被固定在aCNT的表面，而没有任何惰性聚合物粘合剂，这有利于暴露更多的电催化活性位。[TMPyPcCo] 4+和aCNT的有效结合在电化学检测中带来了许多优势，包括电荷的快速定向传输，离子吸附和传输的可渗透通道以及更多的传感位点，因此[TMPyPcCo / aCNTs] n膜对NO2-和H2O2均显示出优异的电化学敏感性。NO2-和H2O2的响应随浓度从5

  DOI：

  10.1039/c5tb01995h

文献信息

• 2-IMINOPYRROLIDINE DERIVATES
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1391451B1

  公开（公告）日：2011-11-23
• Zinc phthalocyanines-mediated photodynamic therapy induces cell death in adenocarcinoma cells
  作者：Stefano Banfi、Enrico Caruso、Loredana Buccafurni、Raffaella Ravizza、Marzia Gariboldi、Elena Monti

  DOI：10.1016/j.jorganchem.2006.11.028

  日期：2007.2

  A panel of eight Zn-phthalocyanines (Zn-Pcs) (1)-(8), differently substituted on the benzo units, was synthesized either by direct cyclic-tetramerization of substituted phthalonitriles (compounds I and 2), or leading from the easily available tetrasulphonyl phthalocyanine to yield the sulfonamido derivatives 3 and 4, or else via the chloromethylation of precedent Zn-Pc followed by reaction with nucleophiles affording the dicationic Zn-Pcs (5) and (6) or the neutral Zn-Pcs (7) and (8). The phototoxicity of these new compounds was evaluated in vitro on human colon adenocarcinoma cell line (HCT116), and their effect compared with those induced by porfimer sodium. The results are reported as IC50 values, following exposure of the cells to different Zn-Pcs concentration and irradiation with a 500 W tungsten/halogen white lamp. The cationic Zn-Pe (5) and (6) together with the Zn-Pc (7), featuring 12 methoxy groups, were found good or fairly good photosensitizers while the more lipophilic Zn-Pcs (1)-(4) and (8) were found devoid of activity. (C) 2006 Elsevier B.V. All rights reserved.
• Physicochemical and photodynamic antimicrobial chemotherapy studies of mono- and tetra-pyridyloxy substituted indium(III) phthalocyanines
  作者：Olawale L. Osifeko、Mahmut Durmuş、Tebello Nyokong

  DOI：10.1016/j.jphotochem.2014.12.011

  日期：2015.3

  The synthesis and photophysicochemical properties of mono- and tetra-pyridyloxy substituted indium (III) phthalocyanines (InPcs) are presented in this study. General trends are described for quantum yields of fluorescence, triplet, singlet oxygen and photodegradation as well as lifetimes of fluorescence and triplet state of these compounds. The complexes exhibited high singlet oxygen quantum yields (Phi(Delta)) ranging from 0.44 to 0.66 in DMF, and from 0.44 to 0.69 in DMSO and Phi(Delta) = 0.31 for the quartenized tetra substituted InPc which is soluble in water. The triplet quantum yields (Phi(T)) ranged from 0.77 to 0.95 in DMF and from 0.77 to 0.94) in DMSO. The tetra substituted photosensitizers do not differ in their inactivation of bacteria with over 8 log reduction of viable bacteria when compared with the mono substituted photosensitizer which could only manage a 1 log reduction. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis, properties, and photodynamic inactivation of Escherichia coli using a cationic and a noncharged Zn(II) pyridyloxyphthalocyanine derivatives
  作者：Inés Scalise、Edgardo N. Durantini

  DOI：10.1016/j.bmc.2005.01.063

  日期：2005.4

  The photodynamic effect of a cationic Zn(II) N-methylpyridyloxyphthalocyanine (ZnPc 2) and a noncharged Zn(II) pyridyloxyphthalocyanine (ZnPc 1) has been compared in both homogeneous media bearing photooxidizable substrates and in vitro using a typical Gram-negative bacterium Escherichia coli. Absorption and fluorescence spectroscopic studies were analyzed in different media. Fluorescence quantum yields (phi(F)) of 0.23 for ZnPc 1 and 0.22 for ZnPc 2 were calculated in N,N-dimethylformamide (DMF). The singlet molecular oxygen, O-2((1)Delta(g)), production was evaluated using 9,10-dimethylanthracene (DMA) in DMF yielding values of Phi(Delta) = 0.56 for ZnPc 1 and 0.59 for ZnPc 2. A faster decomposition Of (L)-tryptophan (Trp), which was used as biological substrate model, was obtained using ZnPc 2 as a sensitizer with respect to ZnPc 1. In biological medium, the E coli cultures were treated with 10 mu M of sensitizer for different times at 37 degrees C in the dark. Both ZnPcs 1 and 2 are rapidly bound to E. coli cells in 5 min and the amount of cell-bound sensitizer is not appreciably changed incubating the cultures for longer times. The recovered ZnPc 2 after one washing step is similar to 3 times higher than 1, reaching a value of similar to 3 nmol/10(6) cells. After irradiation with visible light, a higher photoinactivation of cells was found for ZnPc 2. Thus, a similar to 4.5 log (99.997%) decrease of cell survival was obtained after 30 min of irradiation. On the other hand, a very low photodamage was found for cells treated with ZnPc 1 (similar to 0.5 log). Also, these results were established by stopping of growth curves for E coli. In the structure of ZnPc 2, the cationic centers are isolated from the phthalocyanine ring by an ether bridge, which also provides a higher mobility of the charges facilitating the interaction with the outer membrane of the Gram-negative bacteria. These studies show that cationic ZnPc 2 is an efficient phototherapeutic agent with potential applications in photodynamic inactivation of bacteria. (c) 2005 Elsevier Ltd. All rights reserved.
• Electrocatalytic hydrogen evolution reaction with a supramolecular cobalt(II)phthalocyanine carrying four cobaloxime moieties
  作者：İbrahim Özçeşmeci、Aykut Demir、Duygu Akyüz、Atıf Koca、Ahmet Gül

  DOI：10.1016/j.ica.2017.07.024

  日期：2017.9

  A supramolecular cobalt phthalocyanine (CoPc) bearing four redox active cobaloxime (CoDMG) substituents ((CoDMG)(4)-CoPc) was synthesized and electrochemically characterized in order to determine its functionalities for practical usages as effective electrocatalysts. Voltammetric analyses of CoDMG, CoPc, and (CoDMG)(4)-CoPc indicated redox activity of each compounds and supported substitution of CoPc with CoDMG. (CoDMG)(4)-CoPc showed three CoPc based reduction processes and two CoDMG based reduction processes. While CoDMG showed two reduction and one oxidation processes, CoPc illustrated three reduction and two oxidation processes. Binding of CoDMG to CoPc increased the reduction processes to five. Multi-electron and metal and/or ring based redox processes showed worthy of the (CoDMG)(4)-CoPc for using as an electrocatalyst. Shifting of the proton reduction reaction toward the positive potentials indicated electrocatalytic activities of the complexes for the hydrogen evolution reaction (HER). Among CoDMG, CoPc, and (CoDMG)(4)-CoPc, modified glassy carbon electrode with (CoDMG)(4)-CoPc illustrated the highest electrocatalytic activity and it decreased the over-potential of the bare electrode about 360 mV and increased the current density of the electrode about 10-fold. (C) 2017 Elsevier B.V. All rights reserved.