2-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole | 1073341-55-5

• 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-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole
• 英文别名: 2-(4-Chlorophenyl)-5-pyridin-2-yl-1,3,4-oxadiazole
• CAS: 1073341-55-5
• 化学式: C₁₃H₈ClN₃O
• 分子量: 257.679
• InChiKey: ICZNMKWZAXKTKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 2-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole 以 甲苯 为溶剂， 反应 12.0h， 以57%的产率得到Re(CO)3(2-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole)Br
  参考文献：
  名称：

  Composite nanofibers doped with a phosphorescent Re(I) complex having restricted conjugation plane in its diamine ligand: Preparation, characterization, photophysical property and oxygen-sensing performance

  摘要：

  In this paper, we report a Re(I) complex of Re(CO)(3)(Cl-PYO)Br, where Cl-PYO stands for 2-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole, including its synthesis, identification, molecular structure, theoretical calculation and photophysical character. Re(CO)(3)(Cl-PYO)Br is found to be a yellow emitter with long excited state lifetime in pure N-2 atmosphere. Theoretical calculation result suggests that this emission comes from a triplet metal-to-ligand-charge-transfer excited state. By doping Re(CO)(3)(Cl-PYO)Br into a polymer supporting matrix of poly(vinylpyrrolidone), the emission of the resulted composite materials is found to be sensitive towards various oxygen concentrations. The maximum sensitivity is obtained to be 7.88. Owing to the porous structure of fibrous poly(vinylpyrrolidone) matrix, a short response time of 11 s towards molecular oxygen is also realized with high photostability. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.05.094
• 作为产物：
  描述：

  在 三氯氧磷 作用下， 反应 6.0h， 生成 2-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  基于金属离子触发的1,3,4-恶二唑的分子逻辑门和开关

  摘要：

  用于信息处理应用程序的有机分子设备是构建分子级机器的高度有用的构建基块。能够执行逻辑运算的“智能”分子的发展将使分子级设备和机器的创建成为可能。我们设计了一系列带有2-（对位取代）苯基和5-（邻吡啶基）基团的2,5-二芳基-1,3,4-恶二唑（取代基X = NMe 2，OEt，Me，H和Cl; 1 a – e）形成金属离子的双齿螯合环境。这些化合物对被测金属离子Ni 2 +，Cu 2 +，Zn的荧光响应曲线在发射强度和波长上均发生变化。2+，Cd 2 +，Hg 2+和Pb 2+以及响应取决于取代基X，最重要的是1 d。1,3,4-恶二唑O或N原子和吡啶N原子被确定为金属螯合位点。金属螯合后1 d的荧光响应被用于开发OR，NOR，INHIBIT和EnNOR逻辑门以及“ ON-OFF-ON”和“ OFF-ON-OFF”荧光开关的真值表。 ，3,4-恶二唑分子系统。

  DOI：

  10.1002/chem.200903265

文献信息

• Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds <i>via</i> sp³ C–H functionalization of azaarenes
  作者：Geeta Sai Mani、Kavitha Donthiboina、Nagula Shankaraiah、Ahmed Kamal

  DOI：10.1039/c9nj03573g

  日期：——

  for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole scaffolds has been developed via sp3 C–H functionalization. Gratifyingly, this method involves oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs2CO3. The key features of the present method include good functional group tolerance, a clean protocol, metal-free conditions

  通过sp 3 C–H官能化开发了一种有效的碘介导的一锅合成方案，用于合成2,5-二取代的1,3,4-恶二唑支架。令人欣慰的是，该方法涉及通过使用碘和Cs 2 CO 3进行氧化胺化反应，并伴随碱介导的甲基戊烯和酰基肼的环化反应。本方法的关键特征包括良好的官能团耐受性，清洁的方案，无金属的条件和高收率，使得该方案成为合成生物活性分子及其关键构件的有吸引力的策略。
• Palladium catalyzed direct C–H arylation of 1,3,4-oxadiazole using ligand combination approach
  作者：Sneha Prasad Bakare、Mahendra Patil

  DOI：10.1016/j.tet.2024.133885

  日期：2024.4

  The use of combination of readily available ligands in palladium catalyzed C–H arylation of 1,3,4-oxadiazole with iodoarenes as well as bromoarenes is reported. The combination of phenanthroline monohydrate (Phen.HO) and triphenyl phosphine (PPh) with Pd catalyst exhibited improved catalytical activity compared to a single ligand used separately in the reaction. A wide range of 2,5-diarylated-1,3,4-oxadiazoles

  据报道，在钯催化的 1,3,4-恶二唑与碘芳烃以及溴芳烃的 C-H 芳基化反应中使用易于获得的配体组合。与反应中单独使用的单一配体相比，菲咯啉一水合物 (Phen.HO) 和三苯基膦 (PPh) 与 Pd 催化剂的组合表现出更高的催化活性。使用该方法合成了多种 2,5-二芳基化-1,3,4-恶二唑，其 C-5 位芳基成分有所不同。总体而言，该方法表现出广泛的底物范围和高官能团耐受性。此外，该方法还用于合成咔唑/恶二唑和联苯/恶二唑基杂化化合物，这些化合物以其有趣的光物理性质而闻名。
• Preparation and Acetylcholinesterase Inhibitory Activities of Pyridine-Based 1,3,4-Oxadiazole Derivatives
  作者：Xiang Yu、Yafang Chen、Wude Yang、Xingji Zhou

  DOI：10.3987/com-20-14266

  日期：——
• Molecular Logic Gates and Switches Based on 1,3,4-Oxadiazoles Triggered by Metal Ions
  作者：Ai-Fang Li、Yi-Bin Ruan、Qian-Qian Jiang、Wen-Bin He、Yun-Bao Jiang

  DOI：10.1002/chem.200903265

  日期：2010.5.17

  chelating environment for metal ions. These compounds showed fluorescence response profiles varying in both emission intensity and wavelength toward the tested metal ions Ni2+, Cu2+, Zn2+, Cd2+, Hg2+, and Pb2+ and the responses were dependent on the substituent X, with those of 1 d being the most substantial. The 1,3,4‐oxadiazole O or N atom and pyridine N atom were identified as metal‐chelating sites. The

  用于信息处理应用程序的有机分子设备是构建分子级机器的高度有用的构建基块。能够执行逻辑运算的“智能”分子的发展将使分子级设备和机器的创建成为可能。我们设计了一系列带有2-（对位取代）苯基和5-（邻吡啶基）基团的2,5-二芳基-1,3,4-恶二唑（取代基X = NMe 2，OEt，Me，H和Cl; 1 a – e）形成金属离子的双齿螯合环境。这些化合物对被测金属离子Ni 2 +，Cu 2 +，Zn的荧光响应曲线在发射强度和波长上均发生变化。2+，Cd 2 +，Hg 2+和Pb 2+以及响应取决于取代基X，最重要的是1 d。1,3,4-恶二唑O或N原子和吡啶N原子被确定为金属螯合位点。金属螯合后1 d的荧光响应被用于开发OR，NOR，INHIBIT和EnNOR逻辑门以及“ ON-OFF-ON”和“ OFF-ON-OFF”荧光开关的真值表。 ，3,4-恶二唑分子系统。
• Composite nanofibers doped with a phosphorescent Re(I) complex having restricted conjugation plane in its diamine ligand: Preparation, characterization, photophysical property and oxygen-sensing performance
  作者：Chen Lin、Wang Shaoyan、Wang Qi、Li Jing

  DOI：10.1016/j.saa.2013.05.094

  日期：2013.10

  In this paper, we report a Re(I) complex of Re(CO)(3)(Cl-PYO)Br, where Cl-PYO stands for 2-(4-chlorophenyl)-5-(pyridin-2-yl)-1,3,4-oxadiazole, including its synthesis, identification, molecular structure, theoretical calculation and photophysical character. Re(CO)(3)(Cl-PYO)Br is found to be a yellow emitter with long excited state lifetime in pure N-2 atmosphere. Theoretical calculation result suggests that this emission comes from a triplet metal-to-ligand-charge-transfer excited state. By doping Re(CO)(3)(Cl-PYO)Br into a polymer supporting matrix of poly(vinylpyrrolidone), the emission of the resulted composite materials is found to be sensitive towards various oxygen concentrations. The maximum sensitivity is obtained to be 7.88. Owing to the porous structure of fibrous poly(vinylpyrrolidone) matrix, a short response time of 11 s towards molecular oxygen is also realized with high photostability. (C) 2013 Elsevier B.V. All rights reserved.