2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)phenol | 112020-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)phenol
• 英文别名: 2-(5-Pyridin-4-yl-1,3,4-oxadiazol-2-yl)phenol
• CAS: 112020-92-5
• 化学式: C₁₃H₉N₃O₂
• 分子量: 239.233
• InChiKey: NHEPKNDXNRAHJA-UHFFFAOYSA-N

物化性质

• 熔点：
  230-231 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  460.2±55.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 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：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [RuHCl(CO)(PPh₃)₃] 、 2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)phenol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Ruthenium(II) bis(hydrazone) complexes derived from 1,3,4-oxadiazoles: Synthesis, crystal structure and catalytic application in N-alkylation reactions

  摘要：

  1,3,4-Oxadiazoles (A-C) were derived via a series of reactions between isoniazid and salicylaldehydes. While reacting the oxadiazoles with [RuHCl(CO)(PPh3)(3)] in the presence of NaOH, mononuclear ruthenium(II) complexes bearing 'salen' type N,N'-bis(salicylidene) hydrazone ligands (1-3) were obtained. The oxadiazoles and ruthenium(II) complexes were characterized by analytical and spectral methods. The single crystal XRD analyses of complexes 1 and 2 suggested an octahedral geometry around ruthenium(II) ions in which the bis(hydrazone) act as mononegative bidentate ligands. It was also observed that the presence of an intramolecular hydrogen bonding between the hydroxyl proton and one of the azomethine nitrogens in all the complexes. Further, the complexes were proved as versatile catalysts for the N-alkylation of amines with alcohols under optimized reaction conditions. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2015.01.002
• 作为产物：
  描述：

  异烟酸 在 硫酸 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl)phenol
  参考文献：
  名称：

  Synthesis of Pyridine Clubbed 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives Shows Potent Antimicrobial Activity

  摘要：

  在本研究中，通过使用POCl3作为循环试剂，通过反应各种取代芳香酸和异烟肼酰胺，合成了一系列2,5-二取代-1,3,4-噁二唑类似物（4a-j），保留了吡啶基团。通过色谱数据和光谱数据分析对所有合成化合物的结构阐明。评估了合成化合物对各种ESKAPE病原体的体外抗菌活性。抗菌活性针对枯草芽孢杆菌、大肠杆菌、金黄色葡萄球菌和铜绿假单胞菌进行，而抗真菌活性则对白色念珠菌和曲霉属进行测定。所有合成化合物的体外抗菌研究结果表明，化合物4d和4f表现出与参考药物头孢克肟和依康唑相当的杀菌活性。

  DOI：

  10.2174/1570178617999201130113440

文献信息

• Photophysical Properties of Luminescent Zinc(II)‒Pyridinyloxadiazole Complexes and their Glassy Self‐Assembly Networks
  作者：Barbara Panunzi、Simona Concilio、Rosita Diana、Rafi Shikler、Shiran Nabha、Stefano Piotto、Lucia Sessa、Angela Tuzi、Ugo Caruso

  DOI：10.1002/ejic.201800344

  日期：2018.6.22

  pyridine gave crystalline complexes with the general formula [Zn(Li)2py2]. On the other hand, zinc‐assisted self‐assembly of the ligands in the absence of pyridine led to stable glassy networks with the general stoichiometry [Zn(Li)2]. The direct involvement of the pyridine moiety in the coordination of the metal was observed in all cases. The spectroscopic behaviour of the complexes was explored and compared

  合成了三个包含2,5-二取代-恶二唑单元的多功能配体，包括邻/间/对-取代的吡啶部分。配体与乙酸锌（II）在吡啶中的反应得到通式为[Zn（L i）2 py 2 ]的晶体配合物。另一方面，在不存在吡啶的情况下，配体的锌辅助自组装导致具有稳定的玻璃态网络，具有一般化学计量比[Zn（L i）2]。在所有情况下均观察到吡啶部分直接参与金属的配位。探索并比较了配合物的光谱行为。尤其是，从晶体和玻璃样品产生的薄膜均观察到中到高的光致发光量子产率。通过使用DFT进行光物理行为的合理化，进行了分子和周期计算。
• A facile procedure for the one-pot synthesis of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles
  作者：Minoo Dabiri、Peyman Salehi、Mostafa Baghbanzadeh、Mahboobeh Bahramnejad

  DOI：10.1016/j.tetlet.2006.07.127

  日期：2006.9

  Unsymmetrically 2,5-disubstituted 1,3,4-oxadiazoles were efficiently synthesized from the cyclization–oxidation reaction of acyl hydrazones. Also, the synthesis of the title compounds was achieved by the condensation of acyl hydrazides and aromatic aldehydes in the presence of ceric ammonium nitrate in dichloromethane.

  不对称的2，5-二取代的1,3,4-恶二唑是通过酰基的环化-氧化反应有效合成的。同样，标题化合物的合成是通过在硝酸铈铵中在二氯甲烷中缩合酰肼和芳族醛来实现的。
• Coordination-directed one-dimensional coordination polymers generated from a new unsymmetrical oxadiazole bridging ligand and transition metal ions
  作者：Zhi-Gang Song、Cui-Hong Geng、Jian-Ping Ma、Yu-Bin Dong

  DOI：10.1016/j.inoche.2010.03.032

  日期：2010.7

  (3), have been successfully synthesized based on a new unsymmetrical oxadiazole bridging ligand 2-[2-((3-pyridyl)methoxy)phenyl]-5-[(4-pyridyl)]-1,3,4-oxadiazole (L). Compounds 1–3 feature a similar one-dimensional infinite chain that consists of M2L2 building block (M = Zn(II) and Cd(II)). In 3, the uncoordinated L ligands are located between the [M2L2]n chains and serve as the agents to cross-link

  摘要 三种一维配位聚合物，即[ZnL2(NO3)2]n(1)、[CdL2( )2]n(2)和[ZnL2(H2O)2](ClO4)2•2L•2( )}n (3)，已成功合成基于新的不对称恶二唑桥连配体 2-[2-((3-吡啶基)甲氧基)苯基]-5-[(4-吡啶基)]-1,3， 4-恶二唑 (L)。化合物 1-3 具有类似的一维无限链，由 M2L2 构建块（M = Zn(II) 和 Cd(II)）组成。在图 3 中，未配位的 L 配体位于 [M2L2]n 链之间，并通过弱 π-π 和 H 键相互作用将链交联成二维网络。此外，主要在固态下研究了 L 和 1-3 的发光特性。
• Heteroleptic binuclear copper(I) complexes bearing bis(salicylidene)hydrazone ligands: Synthesis, crystal structure and application in catalytic N-alkylation of amines
  作者：Govindan Prakash、Muthukumaran Nirmala、Rangasamy Ramachandran、Periasamy Viswanathamurthi、Jan Grzegorz Malecki、Jesus Sanmartin

  DOI：10.1016/j.poly.2014.12.015

  日期：2015.3

  A new series of heteroleptic binuclear Cu(I) bis(salicylidene)hydrazone complexes (1-4) bearing triphenylphospine coligands have been synthesized from the reactions of copper(II) precursor complex [CuCl2(PPh3)(2)] with oxadiazole compounds A-D, respectively. It has been observed that the oxadiazole compounds u ndergo ring cleavage with in situ reduction of Cu(II) ion, during the formation of complexes (1-4). The oxadiazoles (A-D) and the Cu(I) complexes (1-4) have been characterized by analytical and spectroscopic methods. Single crystal X-ray diffraction study of complex 2 has revealed a distorted tetrahedral geometry around each Cu(I) center. Catalytic efficiency of the new complexes on the N-alkylation of amines using alcohols was studied under optimized conditions. The new complexes have also been tested for their catalytic activity towards the direct N-alkylation of 2-nitropyridine. (C) 2014 Elsevier Ltd. All rights reserved.
• Pachhamia; Parikh, Journal of the Indian Chemical Society, 1989, vol. 66, # 4, p. 250 - 251
  作者：Pachhamia、Parikh

  DOI：——

  日期：——