4-(2-naphthoxy)phthalonitrile | 201480-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-naphthoxy)phthalonitrile
• 英文别名: 4-(β-naphthyloxy)phthalonitrile；4-(naphthalen-2-yloxy)phthalonitrile；4-(Naphthalen-2-yloxy)-phthalonitrile；4-naphthalen-2-yloxybenzene-1,2-dicarbonitrile
• CAS: 201480-83-3
• 化学式: C₁₈H₁₀N₂O
• 分子量: 270.29
• InChiKey: MVQSGAHWADNELM-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  491.6±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-(2-naphthoxy)phthalonitrile 在 sodium ethanolate 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以42%的产率得到5-(naphthalen-2-yloxy)phthalimide
  参考文献：
  名称：

  Inhibition of monoamine oxidase by C5-substituted phthalimide analogues

  摘要：

  Literature reports that isatin as well as C5- and C6-substituted isatin analogues are reversible inhibitors of human monoamine oxidase (MAO) A and B. In general, C5- and C6-substitution of isatin leads to enhanced binding affinity to both MAO isozymes compared to isatin and in most instances result in selective binding to the MAO-B isoform. Crystallographic and modeling studies suggest that the isatin ring binds to the substrate cavities of MAO-A and -B and is stabilized by hydrogen bond interactions between the NH and the C2 carbonyl oxygen of the dioxoindolyl moiety and water molecules present in the substrate cavities of MAO-A and -B. Based on these observations and the close structural resemblances between isatin and its phthalimide isomer, a series of phthalimide analogues were synthesized and evaluated as MAO inhibitors. While phthalimide and N-aryl-substituted phthalimides were found to be weak MAO inhibitors, phthalimide homologues containing C5 substituents were potent reversible inhibitors of recombinant human MAO-B with IC(50) values ranging from 0.007 to 2.5 mu M and moderately potent reversible inhibitors of recombinant human MAO-A with IC(50) values ranging from 0.22 to 9.0 mu M. By employing molecular docking the importance of hydrogen bonding between the active sites of MAO-A and -B and the phthalimide inhibitors are highlighted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.070
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 2-萘酚 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以76%的产率得到4-(2-naphthoxy)phthalonitrile
  参考文献：
  名称：

  C4取代的邻苯二甲腈对单胺氧化酶的抑制作用

  摘要：

  最近有报道称，一系列C5取代的邻苯二甲酰亚胺是重组人单胺氧化酶（MAO）B的强效可逆抑制剂。建模研究表明，邻苯二甲酰亚胺环与MAO-B底物腔的极性区域形成许多极性相互作用，而C5侧链延伸至范德华相互作用，并通过范德华相互作用与酶进入腔的疏水区相互作用。与两个腔体的相互作用似乎是高亲和力结合的要求。在本研究中，我们已经研究了一系列C4取代的邻苯二甲腈作为潜在的人MAO抑制剂的类似物。发现邻苯二甲腈是高度有效的可逆MAO-B抑制剂，大多数类似物的IC 50均高数值在低nM范围内。邻苯二甲腈也与人MAO-A相互作用，尽管与MAO-B相比具有较低的结合亲和力。模型研究表明，邻苯二甲腈与MAO-B的高结合亲和力可能至少部分取决于腈官能团与酶底物腔之间极性相互作用的形成。对苯甲腈同系物系列的检查确定，对于相应的苯甲腈部分，邻苯二甲腈部分对MAO-B的抑制作用最佳，而与C4取代的苯甲腈相比，C3取代的苯

  DOI：

  10.1016/j.bioorg.2011.10.003

文献信息

• Synthesis and characterization of metal-free and metallo phthalocyanines with four pendant naphthoxy-substituents
  作者：H Yasemin Yenilmez、İbrahim Özçeşmeci、Ali İhsan Okur、Ahmet Gül

  DOI：10.1016/j.poly.2003.12.003

  日期：2004.3

  Abstract Phthalocyanines with four naphthoxy pendant groups on the periphery were prepared by cyclotetramerization of 4-(1-naphthoxy)phthalonitrile and 4-(2-naphthoxy)phthalonitrile. The new compounds were characterized by elemental analyses, 1 H NMR, IR and UV–Vis spectral data. The electronic spectra exhibit an intense π→π * transition of naphthyl identity together with characteristic Q and B bands

  摘要通过4-（1-萘氧基）邻苯二甲腈和4-（2-萘氧基）邻苯二甲腈的环四聚反应制备了具有四个萘氧基侧基的酞菁。这些新化合物的特征在于元素分析，1 H NMR，IR和UV-Vis光谱数据。电子光谱表现出强烈的萘身份的π→π*跃迁以及酞菁核的特征性Q和B谱带。
• Synthesis, fabrication and characterization of 2-naphthyloxy group-substituted bis(2-pyridylimino)isoindoline and its derivatives as a positive electrode for vanadium redox flow battery applications
  作者：Selin Gümrükçü、Mukaddes Özçeşmeci、Nilüfer Koçyiğit、Kerem Kaya、Ahmet Gül、Yücel Şahin、İbrahim Özçeşmeci

  DOI：10.1039/d2dt03547b

  日期：——

  modifiable structure and high stability of 1,3-bis(2-pyridylimino)isoindole (BPIs) compounds make them suitable candidates for many potential applications. In this study, a 1,3-bis(2-pyridylimino)isoindoline derivative bearing a naphthoxy unit and its palladium complex (PdBPI) were synthesized and characterized by single crystal X-ray diffraction, NMR, FT-IR, UV–Vis, and mass spectroscopic methods. The BPI-

  近年来，三齿氮供体配体在无机化学中发挥了重要作用。1,3-双(2-吡啶亚氨基)异吲哚 (BPI) 化合物易于合成、易于修饰的结构和高稳定性使其成为许多潜在应用的合适候选者。在这项研究中，合成了一种带有萘氧基单元的 1,3-双（2-吡啶亚氨基）异二氢吲哚衍生物及其钯络合物 (PdBPI)，并通过单晶 X 射线衍射、NMR、FT-IR、UV-Vis、和质谱方法。BPI 或 PdBPI 改性的铅笔石墨电极通过循环伏安法 (CV)、电化学阻抗谱 (EIS)、扫描电子显微镜 (SEM)、EDX、X 射线光电子能谱 (XPS) 和拉曼光谱。首次研究了这些物质在钒氧化还原液流电池 (VRB) 系统中的效率。在氧化还原液流电池 (RFB) 应用中研究了 BPI 改性碳毡电极 (BPI-CF) 和 PdBPI 改性碳毡电极 (PdBPI-CF) 的行为。这些修饰电极是通过电沉积法获得的。BPI-CF和PdBPI-CF各自的电荷电位分别达到1
• The effect of metal type and gamma irradiation doses on the VOC detection performance of new 1,3-bis(2-pyridylamino)isoindoline complexes
  作者：Selin Gümrükçü、Yalçın Urfa、Ahmet Altındal、Mehmet İsmail Katı、Salih Akyürekli、Ahmet Gül、Yücel Şahin、İbrahim Özçeşmeci

  DOI：10.1016/j.molstruc.2024.139235

  日期：2024.12

  current-time (I–t) measurement set up, respectively. The results of VOC sensing performance have shown that in naphthoxy group substituted 1,3-bis(2-pyridylimino)isoindoline compounds containing nickel and copper metals strongly dependence on the central metal. Under the same conditions, the maximum sensitivity was observed against methanol vapor in the NiBPI-based sensor, while the maximum sensitivity

  本研究合成了含有镍和铜金属的萘氧基取代的 1,3-双（2-吡啶基亚氨基）异吲哚啉化合物，并通过 NMR、FTIR、UV–vis 和质谱方法进行了表征。这些化合物的薄膜沉积在采用旋涂方法装饰有 Au 指间电极结构的 Plexiglas 基板上。然后使用 60Co 作为伽马源，将沉积的薄膜暴露于 1 kGy 和 150 kGy 之间的六剂量伽马射线照射。分别使用原子力显微镜 （AFM） 技术和电流时间 （I-t） 测量装置研究了沉积态和伽马射线照射薄膜的形态和挥发性有机化合物 （VOC） 传感特性。VOC 传感性能结果表明，在萘氧基取代的含有镍和铜金属的 1,3-双（2-吡啶基亚氨基）异吲哚啉化合物中，对中心金属具有很强的依赖性。在相同条件下，基于 NiBPI 的传感器对甲醇蒸气的灵敏度最高，而基于 CuBPI 的传感器对氨蒸气的灵敏度最高。通过检查伽马辐射剂量对传感器 VOC 传感性能的影响
• Novel planar binuclear zinc phthalocyanine sensitizer for dye-sensitized solar cells: Synthesis and spectral, electrochemical, and photovoltaic properties
  作者：Baiqing Zhu、Xuejun Zhang、Mingliang Han、Pengfei Deng、Qiaoling Li

  DOI：10.1016/j.molstruc.2014.09.037

  日期：2015.1

  A planar binuclear zinc phthalocyanine was newly synthesized for use in dye-sensitized solar cells, based on Schiff base and asymmetric amino zinc phthalocyanine. The novel compounds were characterized using FUR, UV-Vis, H-1 NMR, cyclic voltammetry and elemental analysis. From the reduction and oxidation behavior, it is proved that APC and bi-NPC have negative LUMO levels and positive HOMO levels, satisfying the energy gap rule, and can be employed as sensitizers for dye-sensitized solar cells (DSSCs) applications. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis and electrochemical and in situ spectroelectrochemical characterization of manganese, vanadyl, and cobalt phthalocyanines with 2-naphthoxy substituents
  作者：İbrahim Özçeşmeci、Atıf Koca、Ahmet Gül

  DOI：10.1016/j.electacta.2011.03.069

  日期：2011.5

  Metallo (Mn, Co, VO) phthalocyanines bearing peripheral 2-naphthoxy groups were synthesized by cyclotetramerisation of the corresponding phthalonitrile derivative. The phthalocyanine compounds were characterized by elemental analyses, mass, FT-IR and UV-vis spectral data. Three intense bands in the electronic spectra clearly indicate the absorptions resulting from naphthyl groups along with the Q and B bands of the phthalocyanines. Electrochemical and spectroelectrochemical measurements exhibit that incorporation of redox active metal ions, Co-II and Mn-III. into the phthalocyanine core extends the redox capabilities of the Pc ring including the metal-based reduction and oxidation couples of the metal. Presence of molecular oxygen in the electrolyte system affects the voltammetric and spectroelectrochemical responses of the cobalt and manganese phthalocyanines due to the interaction between the complexes and molecular oxygen. Interaction reaction of oxygen with CoPc occurs via an "inner sphere" chemical catalysis process. While CoPc gives the intermediates [O-2(-)-(CoPc-2)-Pc-II](-) and [O-2(2)-(CoPc-2)-Pc-II](2-), MnPc forms mu-oxo MnPcspecies. An in situ electrocolorimetric method has been applied to investigate the color of the electro-generated anionic and cationic forms of the complexes for possible electrochromatic applications. (C) 2011 Elsevier Ltd. All rights reserved.