2-(4-methoxyphenyl)-5-[(E)-2-phenylvinyl]-1,3,4-oxadiazole | 1350919-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-5-[(E)-2-phenylvinyl]-1,3,4-oxadiazole
• 英文别名: 5-(4-methoxyphenyl)-2-(2-phenylethenyl)-1,3,4-oxadiazole；2-(4-methoxyphenyl)-5-[(E)-styryl]-1,3,4-oxadiazole；(E)-2-(4-methoxyphenyl)-5-styryl-1,3,4-oxadiazole；Cambridge id 5131705；2-(4-methoxyphenyl)-5-[(E)-2-phenylethenyl]-1,3,4-oxadiazole
• CAS: 1350919-93-5
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: YFBIGFHENROHJW-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲氧基苯甲酰肼 在 copper(l) iodide 、 lithium tert-butoxide 、 N,N'-二甲基乙二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2-(4-methoxyphenyl)-5-[(E)-2-phenylvinyl]-1,3,4-oxadiazole
  参考文献：
  名称：

  Copper-catalyzed direct cross coupling of 1,3,4-oxadiazoles with trans-β-halostyrenes: synthesis of 2-E-vinyl 1,3,4-oxadiazoles

  摘要：

  The first direct C-H alkenylation of 1,3,4-oxadiazoles with trans-beta-halo olefinic system has been carried out using a combination of Cul/DMEDA as a catalyst. A wide range of 2-E-vinyl-substituted oxadiazoles were obtained in high yields (85-93%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.049

文献信息

• An Improved Synthesis of 2-Aryl- and 2-Alkenyl-1,3,4-oxadiazoles by Using Copper(II) Oxide Nanoparticles as a Catalyst
  作者：Biswanath Das、N. Salva Reddy、P. Raghavendar Reddy

  DOI：10.1055/s-0034-1380923

  日期：——

  Abstract 2-Aryl- and 2-alkenyl-1,3,4-oxadiazoles were efficiently synthesized in high yields by treatment of 1,3,4-oxadiazoles with aryl or alkenyl halides, respectively, in the presence of copper(II) oxide nanoparticles as a catalyst. The reusability of the catalyst is an important advantage in relation to practical applications of this synthesis. 2-Aryl- and 2-alkenyl-1,3,4-oxadiazoles were efficiently

  摘要 通过在氧化铜（II）纳米粒子的存在下分别用芳基或烯基卤化物处理1,3,4-恶二唑，可以高收率高效合成2-芳基和2-烯基-1,3,4-恶二唑作为催化剂。相对于该合成的实际应用，催化剂的可重复使用性是重要的优点。 通过在氧化铜（II）纳米粒子的存在下分别用芳基或烯基卤化物处理1,3,4-恶二唑，可以高收率高效合成2-芳基和2-烯基-1,3,4-恶二唑作为催化剂。相对于该合成的实际应用，催化剂的可重复使用性是重要的优点。
• 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。
• Oxidative cyclization of N-aroylhydrazones to 2-(2-arylethenyl)-1,3,4-oxadiazoles using DDQ as an efficient oxidant
  作者：Karolina Jasiak、Agnieszka Kudelko

  DOI：10.1016/j.tetlet.2015.09.018

  日期：2015.10

  A series of novel 5-aryl-2-(2-arylethenyl)-1,3,4-oxadiazoles were synthesized by the 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) promoted oxidative cyclization of N′-(arylmethylidene)-3-arylacrylohydrazides. A facile and efficient one-pot protocol using the starting 3-arylacrylohydrazides and aromatic aldehydes is also reported. Short reaction times, high yields, a simple work-up procedure and the possibility

  通过2,3-二氯-5,6-二氰基苯并醌（DDQ）促进N '-（芳基亚甲基）的氧化环化反应合成了一系列新型的5-芳基-2-（2-芳基乙烯基）-1,3,4-恶二唑）-3-芳基丙烯酰肼。还报道了一种使用起始的3-芳基丙烯酰肼和芳族醛的简便有效的一锅操作方案。反应时间短，产率高，简单的后处理步骤以及氧化剂再生的可能性使所报道的方法成为合成2,5-二芳基-1,3,4-恶二唑的有前途的替代方法。
• Copper-catalyzed direct cross coupling of 1,3,4-oxadiazoles with trans-β-halostyrenes: synthesis of 2-E-vinyl 1,3,4-oxadiazoles
  作者：Biswanath Das、Gandolla Chinna Reddy、Penagaluri Balasubramanyam、N. Salvanna

  DOI：10.1016/j.tet.2011.10.049

  日期：2012.1

  The first direct C-H alkenylation of 1,3,4-oxadiazoles with trans-beta-halo olefinic system has been carried out using a combination of Cul/DMEDA as a catalyst. A wide range of 2-E-vinyl-substituted oxadiazoles were obtained in high yields (85-93%). (C) 2011 Elsevier Ltd. All rights reserved.