2-Phenyl-5-<2-phenyl-vinyl>-1,3,4-oxadiazol | 1874-31-3

• 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-Phenyl-5-<2-phenyl-vinyl>-1,3,4-oxadiazol
• 英文别名: 5-Phenyl-2-(2-phenyl-ethylenyl)-oxadiazol-1,3,4；2-Phenyl-5-styryl-1,3,4-oxdiazol；5-phenyl-2-styryl-1,3,4-oxadiazole；2-phenyl-5-styryl-[1,3,4]oxadiazole；2-Styryl-5-phenyl-1,3,4-oxadiazol；2-phenyl-5-(2-phenylethenyl)-1,3,4-oxadiazole
• CAS: 1874-31-3
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: MIQDFIINRMWWAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (carbonic acid ethyl ester)-cinnamic acid-anhydride 在 一水合肼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 生成 2-Phenyl-5-<2-phenyl-vinyl>-1,3,4-oxadiazol
  参考文献：
  名称：

  Microwave-assisted synthesis of 2-styryl-1,3,4-oxadiazoles from cinnamic acid hydrazide and triethyl orthoesters

  摘要：

  A novel and efficient synthesis of 2-styryl-1,3,4-oxadiazoles by cyclocondensation of cinnamic acid hydrazide and triethyl orthoesters under microwave irradiation is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.152

文献信息

• Palladium-Catalyzed Cross-Coupling of 1,3,4-Oxadiazoles and Styrenes: An Efficient Method to Synthesize 2-Alkenyl-1,3,4- Oxadiazoles§
  作者：N. Salvanna、Biswanath Das、P. Reddy

  DOI：10.1055/s-0036-1588561

  日期：2018.1

  2-Alkenyl-1,3,4-oxadiazole derivatives have been prepared by cross-coupling of 1,3,4-oxadiazoles with styrenes by using palladium(II) trifluoroacetate [Pd(TFA)2] as a catalyst, 1,10-phenanthroline as a ligand, silver trifluoroacetate as an oxidant, and toluene as a solvent. The products were formed in high yields and no byproducts were detected.

  通过使用二氟乙酸钯(II) [Pd(TFA)2] 作为催化剂，1,10-邻菲啰啉作为配体，三氟乙酸银作为氧化剂，甲苯作为溶剂，通过交叉偶联1,3,4-噁二唑与苯乙烯，制备了2-烯基-1,3,4-噁二唑衍生物。产物收率高，未检测到任何副产物。
• Mechanochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles Mediated by PPh3-TCCA
  作者：Mookda Pattarawarapan、Dolnapa Yamano、Nittaya Wiriya、Wong Phakhodee、Sirawit Wet-osot

  DOI：10.1055/s-0040-1719867

  日期：2022.9

  Mechanochemical synthesis of 2,5-disubstituted 1,3,4-oxadiazoles was developed as an environmentally benign alternative to conventional solvent-based methods. In the presence of triphenylphosphine and trichloroisocyanuric acid, N-acylbenzotriazoles condense with acylhydrazides leading to oxadiazoles derivatives in good to excellent yields within minutes. The approach circumvents the need for strictly

  2,5-二取代 1,3,4-恶二唑的机械化学合成被开发为一种环境友好的替代传统溶剂方法的方法。在三苯基膦和三氯异氰脲酸存在下，N-酰基苯并三唑与酰肼缩合，在几分钟内以良好至极好的收率生成恶二唑衍生物。该方法避免了对严格无水条件、外部加热、长反应时间以及繁琐的多步骤程序的需要。一系列具有反应性功能的底物也具有良好的耐受性。
• Catalytic Application of Electrochemically Prepared Nickel Oxide Nanoparticles to Synthesize 2, 5–Disubstituted-1, 3, 4–Oxadiazoles
  作者：Manisha R. Sawant、Suresh T. Gaikwad、Sushama B. Dare、Anjali S. Rajbhoj

  DOI：10.13005/ojc/360213

  日期：2020.4.28

  The present work aims to synthesize 2,5-disubstituted-1,3,4-oxadiazoles using electrochemically prepared nanoparticles of nickel oxide as catalyst. The nanoparticles thus prepared using electrochemical syntheses are in appreciable yield. The tetrabutyl phosphonium bromide has been used for capping followed by UV, FTIR, XRD, SEM EDS and TEM SAED studies for the characterization. The 2,5-disubstituted-1,3,4-oxadiazoles were synthesized from substituted benzoic acids and their hydrazides in microwave synthesis system using prepared nanoparticles as a catalyst.
• Weidinger,H.; Kranz,J., Chemische Berichte, 1963, vol. 96, p. 1049 - 1058
  作者：Weidinger,H.、Kranz,J.

  DOI：——

  日期：——
• Microwave-assisted synthesis of 2-styryl-1,3,4-oxadiazoles from cinnamic acid hydrazide and triethyl orthoesters
  作者：Agnieszka Kudelko、Wojciech Zieliński

  DOI：10.1016/j.tetlet.2011.10.152

  日期：2012.1

  A novel and efficient synthesis of 2-styryl-1,3,4-oxadiazoles by cyclocondensation of cinnamic acid hydrazide and triethyl orthoesters under microwave irradiation is reported. (C) 2011 Elsevier Ltd. All rights reserved.