3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole | 758695-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole
• 英文别名: Pyridine, 2-[5-phenyl-4-(4-pyridinyl)-4H-1,2,4-triazol-3-yl]-；2-(5-phenyl-4-pyridin-4-yl-1,2,4-triazol-3-yl)pyridine
• CAS: 758695-48-6
• 化学式: C₁₈H₁₃N₅
• 分子量: 299.335
• InChiKey: TZIGNZQQEMNCNU-UHFFFAOYSA-N

物化性质

• 熔点：
  251-253 °C
• 沸点：
  563.9±56.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cadmium(II) iodide 、 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole 以 甲醇 、 水 为溶剂， 以58%的产率得到
  参考文献：
  名称：

  Halide/pseudohalide-directed cadmium(II) coordination polymers based on 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole

  摘要：

  Three new Cd(II) polymers [Cd-2(L-240)(2)I-4](n) (1) [Cd(L-240)(SCN)(2)](n) (2), and [Cd(L-240)(N-3)(2)](n) (3) have been synthesized via the reaction of 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole (L-240) with CdI2 or in the presence of distinct pseudohalide anions (SCN- and N-3(-)). Single-crystal X-ray diffraction indicates that complex I features a 1D coordination chain and further forms a 2D supramolecular network extended via pi center dot center dot center dot pi stacking interactions. Complex 2 shows a 2D layered coordination network and complex 3 has a 3D diamond framework. In complexes 1-3, the Cd-II centers adopt the same octahedral geometry, whereas the L-240 ligands show distinct (mu(3), eta(2)), (mu(4), eta(3)), and (mu(2), eta(2)) binding modes, respectively. These results reveal that such polymeric networks can be well modulated by the halide anion (I-) and pseudohalide anions of SCN- and N-3(-). Thermal stability and fluorescence for complexes 1-3 have been studied. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.03.001
• 作为产物：
  描述：

  碳酸甲丙酯 在 sodium sulfide 、 sulfur 作用下， 以 正丁醇 为溶剂， 反应 72.0h， 生成 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  从 N-取代硫代酰胺到对称和不对称 3,4,5-三取代 4H-1,2,4-三唑：新型螯合配体的合成和表征

  摘要：

  已经开发了在 Willgerodt-Kindler 反应条件下合成 N-取代吡啶-2-硫代甲酰胺的改进方案，使用催化量的硫化钠九水合物。按照该协议，八种携带芳香族或脂肪族 N 取代基的硫代酰胺已以良好的产率制备。这些硫代酰胺或它们的 S-烷基化同系物在回流的 1-丁醇中与酰肼缩合，以良好的收率得到了八个未稠合的 3,4,5-三取代 4H-1,2,4-三唑，包括四个否则不易获得的例子4-烷基-3,5-二芳基-4H-1,2,4-三唑。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400184

文献信息

• Sequential structural transformations via pseudohalide-anion exchange reactions in Cu(II) supramolecular complexes
  作者：Hong-Mei Chen、Wei You、Hongming He、Jing Chen

  DOI：10.1016/j.jssc.2019.07.044

  日期：2019.9

  pseudohalide anion exchanges. Assembly of a rigid angular ligand 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole (L240) with CuBr2 results in a 1D crystalline material [Cu(L240)(Br)2](DMF)(H2O)}n (1). Immersing the green microcrystalline sample of 1 into an aqua solution of NaN(CN)2 (Na(dca)), the partly exchanged blue species [Cu(L240)(dca)Br](H2O)}n (2) is obtained after ca. a week. Then

  我们在这里报告通过拟卤化物阴离子交换的顺序后合成结构转变的第一个例子。刚性角配体3-苯基-5-（2-吡啶基）-4-（4-吡啶基）-4H-1,2,4-三唑（L 240）与CuBr 2的组装产生一维结晶材料[ Cu（L 240）（Br）2 ]（DMF）（H 2 O）} n（1）。浸渍的绿色微晶样品1到的NaN的（CN）一个水溶液2（钠（DCA））时，部分地交换蓝色物种[铜（L 240）（DCA）BR]（H 2 O）} Ñ（2）是在ca. 一周。然后，完全交换的绿色[Cu（L 240）（dca）2 ] n（3）在大约十天后出现，并且2逐渐消失。将1或3进一步浸入NaN 3溶液中，可以获得新的深绿色材料，其定义为[Cu（L 240）（N 3）2 ] 2（4）。这些结构转变可归因于溶剂介导的结构转变，伴随着结晶度，形状，大小和颜色的变化。值得注意的是2 – 4不能由L的直接组件来合成240与那些拟卤化物和Cu盐（DCA
• Mononuclear Low-Spin 3:1-Type Iron(II) Complexes of 4-Substituted 3,5-Bis(2-pyridyl)- and 3-Phenyl-5-(2-pyridyl)-4<i>H</i>-1,2,4-triazoles
  作者：Julia Klingele、Harald Scherer、Marco H. Klingele

  DOI：10.1002/zaac.200900137

  日期：2009.11

  Two series of mononuclear 3:1-type iron(II) complexes have been obtained by the reaction of Fe(ClO4)2·6H2O with nine previously reported 1,2,4-triazole-based ligands. The first series, [FeIILS3](ClO4)2·nH2O, is based on symmetrical 4-substituted 3,5-di-(2-pyridyl)-4H-1,2,4-triazoles where LS = medpt [4-methyl-3,5-di-(2-pyridyl)-4H-1,2,4-triazole], ibdpt [4-isobutyl-3,5-di-(2-pyridyl)-4H-1,2,4-triazole]

  通过 Fe(ClO4)2·6H2O 与九个先前报道的基于 1,2,4-三唑的配体反应，已经获得了两个系列的单核 3:1 型铁 (II) 配合物。第一个系列，[FeIILS3](ClO4)2·nH2O，基于对称的 4-取代 3,5-二-(2-吡啶基)-4H-1,2,4-三唑，其中 LS = medpt [4-甲基-3,5-二-(2-吡啶基)-4H-1,2,4-三唑]，ibdpt [4-异丁基-3,5-二-(2-吡啶基)-4H-1,2,4-三唑], pmdpt [4-(4-甲基苯基)-3,5-二-(2-吡啶基)-4H-1,2,4-三唑], pydpt [3,5-二-(2-吡啶基)- 4-(4-吡啶基)-4H-1,2,4-三唑]和pldpt[3,5-二-(2-吡啶基)-4-(1H-吡咯-1-基)-4H-1,2 ,4-三唑] 而第二系列的配合物 [FeIILU3](ClO4)2·nH2O 包含不对称的
• Two forms of a copper(II) complex of 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole: a six-coordinate monomer versus a five-coordinate polymer
  作者：Marco H. Klingele、Sally Brooker

  DOI：10.1016/j.ica.2004.03.044

  日期：2004.8

  The reaction of the new bidirectional ligand 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole (pyppt) with Cu(ClO4)(2) (.) 6H(2)O in a 2:1 molar ratio in EtOH affords the complex [Cu-II(pyppt)(2)(ClO4)(2)] (.) H2O (1) as a microcrystalline turquoise solid. Recrystallisation of complex 1 from MeCN by vapour diffusion of Et2O gives blue crystals of the monomeric octahedral complex [Cu-II(pyppt)(2)(ClO4)(2)] (.) MeCN (2). In contrast, addition of EtOH to a solution of complex 1 in MeCN followed by slow evaporation yields blue crystals of the five-coordinate polymeric complex [Cu-II(pyppt)(2)](ClO4)(2) (.) EtOH}(infinity) (3). The structures of both complexes have been determined by single crystal X-ray diffraction. (C) 2004 Elsevier B.V. All rights reserved.
• FromN-Substituted Thioamides to Symmetrical and Unsymmetrical 3,4,5-Trisubstituted 4H-1,2,4-Triazoles: Synthesis and Characterisation of New Chelating Ligands
  作者：Marco H. Klingele、Sally Brooker

  DOI：10.1002/ejoc.200400184

  日期：2004.8

  improved protocol for the synthesis of N-substituted pyridine-2-thiocarboxamides under the conditions of the Willgerodt−Kindler reaction, employing a catalytic amount of sodium sulfide nonahydrate, has been developed. Following this protocol, eight thioamides carrying aromatic or aliphatic N-substituents have been prepared in good to excellent yields. Condensation of these thioamides or their S-alkylated

  已经开发了在 Willgerodt-Kindler 反应条件下合成 N-取代吡啶-2-硫代甲酰胺的改进方案，使用催化量的硫化钠九水合物。按照该协议，八种携带芳香族或脂肪族 N 取代基的硫代酰胺已以良好的产率制备。这些硫代酰胺或它们的 S-烷基化同系物在回流的 1-丁醇中与酰肼缩合，以良好的收率得到了八个未稠合的 3,4,5-三取代 4H-1,2,4-三唑，包括四个否则不易获得的例子4-烷基-3,5-二芳基-4H-1,2,4-三唑。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Halide/pseudohalide-directed cadmium(II) coordination polymers based on 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole
  作者：Wei You、Jian-Hua Guo、Cheng-Peng Li、Jing Chen

  DOI：10.1016/j.poly.2015.03.001

  日期：2015.5

  Three new Cd(II) polymers [Cd-2(L-240)(2)I-4](n) (1) [Cd(L-240)(SCN)(2)](n) (2), and [Cd(L-240)(N-3)(2)](n) (3) have been synthesized via the reaction of 3-phenyl-5-(2-pyridyl)-4-(4-pyridyl)-4H-1,2,4-triazole (L-240) with CdI2 or in the presence of distinct pseudohalide anions (SCN- and N-3(-)). Single-crystal X-ray diffraction indicates that complex I features a 1D coordination chain and further forms a 2D supramolecular network extended via pi center dot center dot center dot pi stacking interactions. Complex 2 shows a 2D layered coordination network and complex 3 has a 3D diamond framework. In complexes 1-3, the Cd-II centers adopt the same octahedral geometry, whereas the L-240 ligands show distinct (mu(3), eta(2)), (mu(4), eta(3)), and (mu(2), eta(2)) binding modes, respectively. These results reveal that such polymeric networks can be well modulated by the halide anion (I-) and pseudohalide anions of SCN- and N-3(-). Thermal stability and fluorescence for complexes 1-3 have been studied. (C) 2015 Elsevier Ltd. All rights reserved.