1,3-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene | 3477-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene
• 英文别名: 2-Phenyl-5-[3-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-1,3,4-oxadiazole
• CAS: 3477-75-6
• 化学式: C₂₂H₁₄N₄O₂
• 分子量: 366.379
• InChiKey: BAQYTZSLSKPKEK-UHFFFAOYSA-N

物化性质

• 熔点：
  237-239 °C
• 沸点：
  593.4±60.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene 在 氢氧化钾 作用下， 以 正丁醇 为溶剂， 反应 0.5h， 以70%的产率得到N,N'-bis(benzoyl)terephthalic acid dihydrazide
  参考文献：
  名称：

  An Improved Synthesis of 1,3- and 1,4-Bis[5-aryl-1,3,4-oxadiazol-2-,y1]benzenes via Oxidation of Bis-aroylhydrazones of Iso- and Terephthalaldehyde with Lead(IV) Acetate

  摘要：

  本文描述了异酞醛和对苯二醛的双酰腙与四乙酸铅氧化反应，生成1,3-和1,4-双[5-苯基-1,3,4-噁二唑-2-基]苯。

  DOI：

  10.1055/s-1986-31656
• 作为产物：
  描述：

  3-氰基苯甲酰氯 在 吡啶 、 叠氮化锂 作用下， 以 乙二醇甲醚 为溶剂， 生成 1,3-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene
  参考文献：
  名称：

  Huisgen,R. et al., Chemische Berichte, 1965, vol. 98, p. 2966 - 2984

  摘要：

  DOI：

文献信息

• Synthesis, liquid crystalline behaviour and structure–property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes
  作者：Afef Mabrouki、Malek Fouzai、Armand Soldera、Abdelkader Kriaa、Ahmed Hedhli

  DOI：10.3762/bjoc.16.17

  日期：——

  Two series containing 1,3-bis(1,3,4-oxadiazol-2-yl)benzene as a rigid core (RC) and alkyl or perfluoroalkyl as terminal chains were synthesized and characterized. Liquid crystal properties of the synthesized compounds have been investigated by polarizing optical microscopy, differential scanning calorimetry and X-ray diffraction techniques. Conformation effects of the synthesized products on the dipole

  合成并表征了包含1,3-双（1,3,4-恶二唑-2-基）苯作为刚性核（RC）和烷基或全氟烷基作为末端链的两个系列。已通过偏光光学显微镜，差示扫描量热法和X射线衍射技术研究了合成化合物的液晶性质。还研究了合成产物对偶极矩的构象效应。
• UV‐Induced 1,3,4‐Oxadiazole Formation from 5‐Substituted Tetrazoles and Carboxylic Acids in Flow
  作者：Luke Green、Keith Livingstone、Sophie Bertrand、Simon Peace、Craig Jamieson

  DOI：10.1002/chem.202002896

  日期：2020.11.20

  A range of 1,3,4‐oxadiazoles have been synthesized using a UV‐B activated flow approach starting from carboxylic acids and 5‐substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino

  已使用UV-B活化流动法从羧酸和5-取代的四唑合成了1,3,4-恶二唑。紫外线的应用代表了传统热解方法的一种有吸引力的替代方法，并已证明具有可比的效率和多功能性，具有多种底物范围，包括掺入高度取代的氨基酸。
• Weidinger,H.; Kranz,J., Chemische Berichte, 1963, vol. 96, p. 1049 - 1058
  作者：Weidinger,H.、Kranz,J.

  DOI：——

  日期：——
• Excited State Luminescence of Multi-(5-phenyl-1,3,4-oxadiazo-2-yl)benzenes in an Electron-Donating Matrix: Exciplex or Electroplex?
  作者：Chih-Chiang Yang、Chia-Jung Hsu、Pi-Tai Chou、Hsu Chun Cheng、Yuhlong Oliver Su、Man-kit Leung

  DOI：10.1021/jp9093063

  日期：2010.1.21

  Multi-(5-phenyl-1,3,4-oxadiazo-2-yl)benzenes show emission in organic solvents from ultraviolet to blue (339-447 nm). The reduction potentials E-1/2(red) cover a large range of -2.11 V for 2,5-diphenyl-1,3,4-oxadiazole to -0.76 V for l,2,3,4,5,6-hexa(5-phenyl-1,3,4-oxadiazo-2-yl)benzene. An unexpectedly wide spectral range of the oxadiazole (OXD) exciplex emissions in PVK is observed, ranging from 406 to 603 nm. The OXDs also exhibit similar electroluminescence (EL) when blended into polyvinylcarbazole (PVK). A linear correlation between the lambda(max) of the electroluminescence and photoluminescence is observed, implying that the emission mechanisms in both processes are similar. In addition, the linear correlation between the E-1/2(red) versus of lambda(max) of EL (eV) reflected that the term of the charge-transfer configuration of the contact electron-hole pair plays a major role in the exciplex emission. The exciplex EL of 1,2,5-tri(5-phenyl- 1,3,4-oxadiazo-2-yl)benzene (5) could be as high as 1.0 cd/A. Since the exciplex emission usually has a large Stokes shift, this provides a window for us to generate duo emissions for near white light EL with high efficiency. Among the devices we tried, the device of PVK/2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole/5/2,5,8,11-tetra-tert-butylperylene (100: 40:40:4) gave EL with good current efficiency of 1.63 cd/A.
• REKKAS, S. A.;RODIOS, N. A.;ALEXANDROU, N. E., SYNTHESIS, BRD, 1986, N 5, 411-413
  作者：REKKAS, S. A.、RODIOS, N. A.、ALEXANDROU, N. E.

  DOI：——

  日期：——