2-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole | 5378-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
• CAS: 5378-26-7
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: GUSYHPMVEXGYSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 、 (E)-4-(2-bromovinyl)-1,1'-biphenyl 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， 以78%的产率得到(E)-2-(2-(biphenyl-4-yl)vinyl)-5-(3,4,5-trimethoxyphenyl)-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
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰肼 、 原甲酸三乙酯 生成 2-(3,4,5-trimethoxyphenyl)-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

• 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。
• K₂CO₃-mediated, direct C–H bond selenation and thiolation of 1,3,4-oxadiazoles in the absence of metal catalyst: an eco-friendly approach
  作者：Jamal Rafique、Sumbal Saba、Alisson R. Rosário、Gilson Zeni、Antonio L. Braga

  DOI：10.1039/c4ra10490k

  日期：——

  An eco-friendly, straightforward and high-yielding methodology for the synthesis of chalcogenyl oxadiazoles via the K₂CO₃-promoted direct C–H bond chalcogenation of 2-substituted-1,3,4-oxadiazoles is described herein.

  这里描述了一种环保、简单且高产的方法，通过K₂CO_{3促进的直接C-H键硫、硒、碲化合物氧代噻二唑的合成。}
• Maillard,J. et al., Bulletin de la Societe Chimique de France, 1966, p. 376 - 381
  作者：Maillard,J. et al.

  DOI：——

  日期：——
• 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.
• Spectral-Luminescent Properties of 2-Aryl-1,3,4-oxadiazoles
  作者：I. E. Mikhailov、Yu. M. Artyushkina、G. A. Dushenko、O. I. Mikhailova、Yu. V. Revinskii、V. I. Minkin

  DOI：10.1134/s1070363218030349

  日期：2018.3

  Refluxing equimolar amounts of acylhydrazides with triethyl orthoformate in o-xylene yielded 2-aryl-1,3,4-oxadiazoles luminescing with high quantum yields in polar and nonpolar solvents (lambda(fl)(max) 299-349 nm, phi 0.20-0.62). The only exception was 2-(1,3,4-oxadiazol-2-yl)phenol emitting intensely only in highly polar aprotic DMSO (lambda(fl)(max) 350 nm, phi 0.19).