2-(2-methoxyphenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole | 93014-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-methoxyphenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole
• CAS: 93014-12-1
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: LNBGHPOBQIASEW-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  454.0±55.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲氧基苯甲酸甲酯 在 碘苯二乙酸 、 diazenium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(2-methoxyphenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives and evaluation of their antiglycation potential

  摘要：

  In the search of potent antidiabetic drug, we synthesized 1-25 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives. First, we synthesized 2-methoxybenzohydrazide from methyl 2-methoxybenzoate which was treated with different arylaldehydes to afford 1-25 compounds. The synthesized compounds were evaluated for antiglycation activity. We found that 1-6 and 8 showed potent activity ranging from 160.2 to 290.17 A mu M better than standard drug rutin (IC50 = 295.09 +/- A 1.04 A mu M). All the synthesized compounds were characterized by different spectroscopy methods. These compounds can further be studied to develop lead antidiabetic compounds.

  DOI：

  10.1007/s00044-015-1476-8

文献信息

• UV‐Induced 1,3,4‐Oxadiazole Formation from 5‐Substituted Tetrazoles and Carboxylic Acids in Flow
  作者：Luke Green、Keith Livingstone、Sophie Bertrand、Simon Peace、Craig Jamieson

  DOI：10.1002/chem.202002896

  日期：2020.11.20

  A range of 1,3,4‐oxadiazoles have been synthesized using a UV‐B activated flow approach starting from carboxylic acids and 5‐substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino

  已使用UV-B活化流动法从羧酸和5-取代的四唑合成了1,3,4-恶二唑。紫外线的应用代表了传统热解方法的一种有吸引力的替代方法，并已证明具有可比的效率和多功能性，具有多种底物范围，包括掺入高度取代的氨基酸。
• Direct Palladium‐Catalyzed C5‐Arylation of 1,3,4‐Oxadiazoles with Aryl Chlorides Promoted by Bis(di‐isopropylphosphino) Ferrocene
  作者：Loris Gelin、Henri Sabbadin、Hélène Cattey、Paul Fleurat‐Lessard、Jean‐Cyrille Hierso、Julien Roger

  DOI：10.1002/ejoc.202400212

  日期：2024.6.3

  The palladium-catalyzed direct arylation of 1,2,4-oxadiazoles proceeds efficiently at low catalyst loading (0.5 to 1 mol %) with the decisive assistance of sterically constrained ferrocenyldiphosphane ligands. This protocol tolerates electron-donating and electron-withdrawing substituents on the (heteroaryl)aryl halide.

  在空间约束的二茂铁基二膦配体的决定性帮助下，钯催化的 1,2,4-恶二唑的直接芳基化反应在低催化剂负载量（0.5 至 1 mol %）下有效进行。该方案允许（杂芳基）芳基卤化物上的给电子和吸电子取代基。