1,2-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene

• 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: 1,2-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene
• 英文别名: 2-Phenyl-5-[2-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]-1,3,4-oxadiazole
• 化学式: C₂₂H₁₄N₄O₂
• 分子量: 366.379
• InChiKey: PYRXTHWDCLZQFO-UHFFFAOYSA-N

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

• 作为产物：
  描述：

  N-(1-((2-benzoyl)hydrazono)isoindolin-2-yl)benzamide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到1,2-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene
  参考文献：
  名称：

  N-（1-（2-（芳基-肼基）异吲哚-2-基）苯甲酰胺的意外形成并将其转化为1,2-（Bis-1,3,4-恶二唑-2-基）苯

  摘要：

  邻苯二甲醛与各种芳酰基肼之间的反应出乎意料地产生了N-（1-（2-芳基-肼基）异吲哚啉-2-基）苯甲酰胺以及可预测的1,2-双-芳酰基hydr。主要反应产物的NMR研究表明，存在各种比例的几何异构体混合物。单晶X射线衍射证实了所提出的结构，并表明了C═N双键取代基的Z构型。缩合反应条件的优化使得能够定量分离环状异构体。用双（三氟乙酰氧基）碘苯（PIFA）氧化异构体导致快速形成新的高荧光1,2-双（5-芳基-1,3,4-恶二唑-2-基）苯。

  DOI：

  10.1021/jo400023z

文献信息

• Palladium catalyzed direct C–H arylation of 1,3,4-oxadiazole using ligand combination approach
  作者：Sneha Prasad Bakare、Mahendra Patil

  DOI：10.1016/j.tet.2024.133885

  日期：2024.4

  The use of combination of readily available ligands in palladium catalyzed C–H arylation of 1,3,4-oxadiazole with iodoarenes as well as bromoarenes is reported. The combination of phenanthroline monohydrate (Phen.HO) and triphenyl phosphine (PPh) with Pd catalyst exhibited improved catalytical activity compared to a single ligand used separately in the reaction. A wide range of 2,5-diarylated-1,3,4-oxadiazoles

  据报道，在钯催化的 1,3,4-恶二唑与碘芳烃以及溴芳烃的 C-H 芳基化反应中使用易于获得的配体组合。与反应中单独使用的单一配体相比，菲咯啉一水合物 (Phen.HO) 和三苯基膦 (PPh) 与 Pd 催化剂的组合表现出更高的催化活性。使用该方法合成了多种 2,5-二芳基化-1,3,4-恶二唑，其 C-5 位芳基成分有所不同。总体而言，该方法表现出广泛的底物范围和高官能团耐受性。此外，该方法还用于合成咔唑/恶二唑和联苯/恶二唑基杂化化合物，这些化合物以其有趣的光物理性质而闻名。
• 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.
• Myznikov, Yu. E.; Koldobskii, G. I.; Ostrovskii, B. A., Journal of general chemistry of the USSR, 1992, vol. 62, # 6.2, p. 1125 - 1128
  作者：Myznikov, Yu. E.、Koldobskii, G. I.、Ostrovskii, B. A.、Poplavskii, V. S.

  DOI：——

  日期：——
• Unexpected Formation of <i>N</i>-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes
  作者：Codruţa C. Paraschivescu、Mihaela Matache、Cristian Dobrotă、Alina Nicolescu、Cătălin Maxim、Călin Deleanu、Ileana C. Fărcăşanu、Niculina D. Hădade

  DOI：10.1021/jo400023z

  日期：2013.3.15

  mixture of geometrical isomers, in various ratios. Single crystal X-ray diffraction confirms the proposed structure and indicates a Z configuration of the C═N double bond substitutents. Optimization of the condensation reaction conditions enabled quantitative isolation of the cyclic isomer. Oxidation of the isomers with bis(trifluoroacetoxy)iodobenzene (PIFA) leads to rapid formation of new highly fluorescent

  邻苯二甲醛与各种芳酰基肼之间的反应出乎意料地产生了N-（1-（2-芳基-肼基）异吲哚啉-2-基）苯甲酰胺以及可预测的1,2-双-芳酰基hydr。主要反应产物的NMR研究表明，存在各种比例的几何异构体混合物。单晶X射线衍射证实了所提出的结构，并表明了C═N双键取代基的Z构型。缩合反应条件的优化使得能够定量分离环状异构体。用双（三氟乙酰氧基）碘苯（PIFA）氧化异构体导致快速形成新的高荧光1,2-双（5-芳基-1,3,4-恶二唑-2-基）苯。