2-(3,4-dimethylphenyl)-5-phenyl-1,3,4-oxadiazole

• 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: 2-(3,4-dimethylphenyl)-5-phenyl-1,3,4-oxadiazole
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: NBYJNUCPLRWPNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethylphenyl)-5-phenyl-1,3,4-oxadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 苯 为溶剂， 反应 9.5h， 生成 2-[3,4-Bis[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Optically Acid-Sensory and Electrochemical Properties of Novel Polyoxadiazole Derivatives

  摘要：

  A series of PPV-based polyoxadiazoles have been synthesized by Homer and Suzuki coupling polymerization to investigate their structure-property relationship. These copolymers exhibit good thermal stability (decomposition temperature around 352-413 degreesC). Excimer formation in P4-P9 was confirmed by their absorption and PL spectral peak transition in solution at different concentrations and in thin films. Unusual absorption and fluorescence were observed in acid media and have been related to photoinduced charge transfer in alternating donor-acceptor architecture. The photoinduced charge transfer led to a blue shift in iminodibenzyl-containing copolymers (P1-P3) and a red shift in fluorene-containing copolymers (P9), reflecting the fact that iminodibenzyl is a stronger electron-donating unit. The electrochemical properties of the copolymers were evaluated by cyclic voltammetry and their highest occupied molecular orbital and the lowest unoccupied molecular orbit energy levels were estimated. The optical band gaps of the dioxadiazole-containing copolymers show great discrepancy with the electrochemical band gap energy due to the donor-acceptor feature of the dioxadiazole unit.

  DOI：

  10.1021/ma035576y
• 作为产物：
  描述：

  3,4-二甲基苯甲酸甲酯 在 吡啶 、 一水合肼 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 13.0h， 生成 2-(3,4-dimethylphenyl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Optically Acid-Sensory and Electrochemical Properties of Novel Polyoxadiazole Derivatives

  摘要：

  A series of PPV-based polyoxadiazoles have been synthesized by Homer and Suzuki coupling polymerization to investigate their structure-property relationship. These copolymers exhibit good thermal stability (decomposition temperature around 352-413 degreesC). Excimer formation in P4-P9 was confirmed by their absorption and PL spectral peak transition in solution at different concentrations and in thin films. Unusual absorption and fluorescence were observed in acid media and have been related to photoinduced charge transfer in alternating donor-acceptor architecture. The photoinduced charge transfer led to a blue shift in iminodibenzyl-containing copolymers (P1-P3) and a red shift in fluorene-containing copolymers (P9), reflecting the fact that iminodibenzyl is a stronger electron-donating unit. The electrochemical properties of the copolymers were evaluated by cyclic voltammetry and their highest occupied molecular orbital and the lowest unoccupied molecular orbit energy levels were estimated. The optical band gaps of the dioxadiazole-containing copolymers show great discrepancy with the electrochemical band gap energy due to the donor-acceptor feature of the dioxadiazole unit.

  DOI：

  10.1021/ma035576y

文献信息

• One-pot cyclization/decarboxylation of α-keto acids and acylhydrazines for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under transition-metal-free conditions
  作者：Peng Gao、Juan Wang、Zijing Bai、Hualei Cheng、Jian Xiao、Mengnan Lai、Desuo Yang、Mingjin Fan

  DOI：10.1016/j.tetlet.2016.09.007

  日期：2016.10

  A one-pot KI/TBHP-mediated oxidative cyclization of α-keto acids with acylhydrazines was developed. A series of functional 2,5-disubstituted 1,3,4-oxadiazoles were synthesized through a tandem keto amine condensation followed by oxidative cyclization and decarboxylation reactions. This procedure was achieved under transition-metal-free conditions and showed advantages including readily available materials

  开发了单罐KI / TBHP介导的α-酮酸与酰肼的氧化环化反应。通过串联酮胺缩合，然后进行氧化环化和脱羧反应，合成了一系列功能性的2,5-二取代的1,3,4-恶二唑。该方法是在无过渡金属的条件下完成的，并显示出以下优点：容易获得的材料，温和的反应条件和良好的基团耐受性。
• Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions
  作者：Chengrong Ding、Guofu Zhang、Yidong Yu、Yiyong Zhao、Xiaoqiang Xie

  DOI：10.1055/s-0036-1588747

  日期：2017.7

  A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O2.

  开发了一种简单高效的阳离子 Fe(III)/TEMPO 催化的芳酰腙氧化环化反应，用于合成 2,5-二取代的 1,3,4-恶二唑衍生物。该反应在O 2存在的温和条件下具有广泛的范围、良好的官能团耐受性和高产率。
• 一种制备2,5-二取代-1,3,4-噁二唑的方法
  申请人：浙江工业大学

  公开号：CN106905257B

  公开（公告）日：2019-10-29

  本发明提供了一种催化氧化环化制备式(II)所示的1,3,4‑噁二唑的方法，所述方法为：以结构如式(I)所示的甲酰腙化合物为原料，以空气或氧气气氛下，以硝酸铁为催化剂，以2,2,6,6‑四甲基哌啶氮氧化物为引发剂，在吸水剂的作用下，在吸水剂的作用下，在有机溶剂中，于25～60℃下反应3～12h，所得反应液经后处理得到式(II)所示的1,3,4‑噁二唑化合物；本发明反应速度快、条件温和，操作方便，成本低，反应安全，整个过程对环境友好，无污染。
• Synthesis and Optically Acid-Sensory and Electrochemical Properties of Novel Polyoxadiazole Derivatives
  作者：Tzi-Yi Wu、Rong-Bin Sheu、Yun Chen

  DOI：10.1021/ma035576y

  日期：2004.2.1

  A series of PPV-based polyoxadiazoles have been synthesized by Homer and Suzuki coupling polymerization to investigate their structure-property relationship. These copolymers exhibit good thermal stability (decomposition temperature around 352-413 degreesC). Excimer formation in P4-P9 was confirmed by their absorption and PL spectral peak transition in solution at different concentrations and in thin films. Unusual absorption and fluorescence were observed in acid media and have been related to photoinduced charge transfer in alternating donor-acceptor architecture. The photoinduced charge transfer led to a blue shift in iminodibenzyl-containing copolymers (P1-P3) and a red shift in fluorene-containing copolymers (P9), reflecting the fact that iminodibenzyl is a stronger electron-donating unit. The electrochemical properties of the copolymers were evaluated by cyclic voltammetry and their highest occupied molecular orbital and the lowest unoccupied molecular orbit energy levels were estimated. The optical band gaps of the dioxadiazole-containing copolymers show great discrepancy with the electrochemical band gap energy due to the donor-acceptor feature of the dioxadiazole unit.