2-[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]phenol | 880355-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]phenol
• 英文别名: 2-[5-(3,4,5-Trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]phenol
• CAS: 880355-08-8
• 化学式: C₁₇H₁₆N₂O₅
• mdl: MFCD03444739
• 分子量: 328.324
• InChiKey: ITGGIUHONKKOIY-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  505.4±60.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]phenol 、 碘乙烷 在 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以86%的产率得到2-(2-ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, structure, spectral and luminescence properties of the tetracoordinated diphenylboron and zinc complexes with 1,3,4-oxadiazole and 1,2,4-triazole ligands

  摘要：

  The new diphenylboron 1c, 2c and zinc 1d, 2d complexes with 2-(2-hydroxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 1a and 1-phenyl-3-methyl-1,2,4-triazole 2a as the chelating ligands and O-ethyl derivatives 1b, 2b of these ligands have been synthesized and their UV-Vis and photoluminescence studied. Molecular structures of the chelate diphenylboron complexes 1c and 2c were determined by X-ray single-crystal diffraction. Spectroscopic properties of all the compounds, including excited state intramolecular proton transfer (ESIPT) rearrangements observed in ligands 1a and 2a were analyzed using DFT and TD DFT calculations. The emission spectra of ligands 1a, 2a contain a moderate intensity band (phi 0.07, 0.19) in DMSO and two low intensity bands (phi 0.002-0.012) in other solvents. 2-(2-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 1b and all the complexes exhibit significant fluorescence both in polar and non-polar solvents in the blue region of the spectrum, 1b: phi 0.84-0.96, lambda(fl)(max) 363-406 nm: 1c,d, 2c,d: phi 0.43-0.65, lambda(fl)(max) 429-457 nm. The displayed spectral characteristics make these complexes promising for the use as blue emitters in the design of light-emitting organic diodes. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2019.03.044
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰氯 在 氯化亚砜 、 sodium carbonate 作用下， 生成 2-[5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazol-2-yl]phenol
  参考文献：
  名称：

  2-[2-甲基(乙酰基，甲苯磺酰基)氧基苯基]-5-(3,4,5-三甲氧基苯基)-1,3,4-恶二唑的发光光谱性质

  摘要：

  摘要 N'-芳酰基苯甲酰肼在亚硫酰氯中环化脱水得到 2-(2-羟基苯基)-5-(3,4,5-三甲氧基苯基)-1,3,4-恶二唑及其 2-(2-甲氧基苯基) 类似物。2-(2-羟基苯基)-5-(3,4,5-三甲氧基苯基)-1,3,4-恶二唑的乙酰化和甲苯磺酰化得到 2-乙酰氧基苯基和 2-甲苯磺酰氧基苯基衍生物。2-[2-甲氧基（乙酰氧基，甲苯磺酰氧基）苯基]-5-（3,4,5-三甲氧基苯基）-1,3,4-恶二唑在蓝紫色区域显示出强烈的发光（φ0.22-0.99） λ 364–453 nm 范围内的发射最大值。研究了溶剂极性对这些化合物的吸收和发射光谱的影响。

  DOI：

  10.1134/s1070428022100232

文献信息

• An expeditious, solvent-free synthesis of some 5-aryl-2-(2-hydroxyphenyl)-1,3,4-oxadiazoles
  作者：Aamer Saeed

  DOI：10.1007/s10593-007-0167-x

  日期：2007.8
• Synthesis and luminescence properties of 2-(2-benzoyloxyphenyl)-5-aryl-1,3,4-oxadiazoles
  作者：A. D. Beldovskaya、G. A. Dushenko、N. I. Vikrishchuk、L. D. Popov、Yu. V. Revinskii、I. E. Mikhailov、V. I. Minkin

  DOI：10.1134/s1070428013120312

  日期：2013.12
• Synthesis, structure, spectral and luminescence properties of the tetracoordinated diphenylboron and zinc complexes with 1,3,4-oxadiazole and 1,2,4-triazole ligands
  作者：Igor E. Mikhailov、Galina A. Dushenko、Mikhail E. Gurskii、Natalia I. Vikrischuk、Leonid D. Popov、Yurii V. Revinskii、Konstantin A. Lyssenko、Vladimir I. Minkin

  DOI：10.1016/j.poly.2019.03.044

  日期：2019.7

  The new diphenylboron 1c, 2c and zinc 1d, 2d complexes with 2-(2-hydroxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 1a and 1-phenyl-3-methyl-1,2,4-triazole 2a as the chelating ligands and O-ethyl derivatives 1b, 2b of these ligands have been synthesized and their UV-Vis and photoluminescence studied. Molecular structures of the chelate diphenylboron complexes 1c and 2c were determined by X-ray single-crystal diffraction. Spectroscopic properties of all the compounds, including excited state intramolecular proton transfer (ESIPT) rearrangements observed in ligands 1a and 2a were analyzed using DFT and TD DFT calculations. The emission spectra of ligands 1a, 2a contain a moderate intensity band (phi 0.07, 0.19) in DMSO and two low intensity bands (phi 0.002-0.012) in other solvents. 2-(2-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 1b and all the complexes exhibit significant fluorescence both in polar and non-polar solvents in the blue region of the spectrum, 1b: phi 0.84-0.96, lambda(fl)(max) 363-406 nm: 1c,d, 2c,d: phi 0.43-0.65, lambda(fl)(max) 429-457 nm. The displayed spectral characteristics make these complexes promising for the use as blue emitters in the design of light-emitting organic diodes. (C) 2019 Elsevier Ltd. All rights reserved.
• Luminescence Spectral Properties of 2-[2-Methyl(Acetyl, Tosyl)oxyphenyl]-5-(3,4,5-trimethoxy-phenyl)-1,3,4-oxadiazoles
  作者：I. E. Mikhailov、N. I. Vikrishchuk、L. D. Popov、G. A. Dushenko、V. I. Minkin

  DOI：10.1134/s1070428022100232

  日期：2022.10

  Abstract Cyclodehydration of N′-aroylbenzohydrazides in thionyl chloride gave 2-(2-hydroxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole and its 2-(2-methoxyphenyl) analog. Acetylation and tosylation of 2-(2-hydroxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole afforded 2-acetoxyphenyl and 2-tosyloxy­phenyl derivatives. 2-[2-Methoxy(acetoxy, tosyloxy)phenyl]-5-(3,4,5-trimethoxyphenyl)-1,3

  摘要 N'-芳酰基苯甲酰肼在亚硫酰氯中环化脱水得到 2-(2-羟基苯基)-5-(3,4,5-三甲氧基苯基)-1,3,4-恶二唑及其 2-(2-甲氧基苯基) 类似物。2-(2-羟基苯基)-5-(3,4,5-三甲氧基苯基)-1,3,4-恶二唑的乙酰化和甲苯磺酰化得到 2-乙酰氧基苯基和 2-甲苯磺酰氧基苯基衍生物。2-[2-甲氧基（乙酰氧基，甲苯磺酰氧基）苯基]-5-（3,4,5-三甲氧基苯基）-1,3,4-恶二唑在蓝紫色区域显示出强烈的发光（φ0.22-0.99） λ 364–453 nm 范围内的发射最大值。研究了溶剂极性对这些化合物的吸收和发射光谱的影响。