2-naphthalen-2-yl-5-phenyl-[1,3,4]oxadiazole | 967-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthalen-2-yl-5-phenyl-[1,3,4]oxadiazole
• 英文别名: 2-(2''-naphthyl)-5-(phenyl)-1,3,4-oxadiazole；2-(2-naphthalenyl)-5-phenyl-1,3,4-oxadiazole；[2]naphthyl-phenyl-[1,3,4]oxadiazole；[2]Naphthyl-phenyl-[1,3,4]oxadiazol；2-(2-naphthyl)-5-phenyl-1,3,4-oxadiazole；5-<2>Naphthyl-2-phenyl-1,3,4-oxadiazol；2-naphthalen-2-yl-5-phenyl-1,3,4-oxadiazole
• CAS: 967-72-6
• 化学式: C₁₈H₁₂N₂O
• 分子量: 272.306
• InChiKey: PFFNHKOLVBEBJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-benzoyl-N'-[2]naphthoyl-hydrazine 在 N,N-二异丙基乙胺 、 对甲苯磺酰氯 作用下， 以 乙腈 为溶剂， 生成 2-naphthalen-2-yl-5-phenyl-[1,3,4]oxadiazole
  参考文献：
  名称：

  Mild and convenient one-pot synthesis of 1,3,4-oxadiazoles

  摘要：

  A mild, general, convenient, and efficient one-pot synthesis of 2-phenyl-5-substituted-1,3,4-oxadiazoles is described. Both (hetero)aryl and alkyl carboxylic acids were efficiently condensed with benzohydrazide in the presence of TBTU to give diacylhydrazine intermediates. The latter underwent a smooth TsCl-mediated cyclodehydration reaction to afford 2-phenyl-5-substituted-1,3,4-oxadiazoles in good to very good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.139

文献信息

• Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents
  作者：Sushma Singh、Laxmi Kant Sharma、Apoorv Saraswat、Ibadur R. Siddiqui、Harbans K. Kehri、Rana K. Pal Singh

  DOI：10.1039/c3ra21904f

  日期：——

  The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis. The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4-oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds.

  在甲醇溶液中，以NaClO4为支持电解质，通过循环伏安法和控制电位电解法研究了醛-N-芳酰腙的电化学氧化反应。结果表明，在室温条件下，在不分隔的铂电极反应池中，醛-N-芳酰腙成功进行了分子内环化反应，得到了较高产率的相应1,3,4-噁二唑类化合物。通过光谱方法对反应产物进行了表征，并从伏安法研究中推导出反应机理。对合成化合物进行了对 Fusarium oxysporum、Alternaria solani、Candida albicans 和 Aspergillus niger 的抗真菌活性评估。结果显示，所有合成化合物对测试的真菌均显示出显著的抗真菌活性。其中，合成衍生物 7b、7d、7g、7h、7i、7j 和 7r 被发现是最高效的抗真菌化合物。
• Visible-light-promoted aerobic oxidative cyclization to access 1,3,4-oxadiazoles from aldehydes and acylhydrazides
  作者：Arvind K. Yadav、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2014.02.022

  日期：2014.3

  A novel and practical access to symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles directly from aldehydes and acylhydrazides using visible light irradiation under an air atmosphere in the presence of eosin Y as an organophotoredox catalyst at rt is reported. This is the first example of oxidative cyclization of acylhydrazones employing air and visible light as inexpensive, readily available

  报道了在室温下在曙红Y作为有机光氧化还原催化剂存在下，在空气气氛下使用可见光照射，从可见光和光直接从醛和酰肼直接，对称地和不对称地合成对称和不对称的2,5-二取代的1,3,4-恶二唑的方法。这是使用空气和可见光作为廉价，易于获得，无毒且可持续的试剂对酰基hydr进行氧化环化的第一个例子。
• One-pot carbonylation-dehydration tandem reaction of aryl iodides with acylhydrazines for synthesis of 2,5-diaryl-1,3,4-oxadiazoles
  作者：Lin Guo、Shu-Qing Yang、Kai-Chun Zhao、Xiao-Chao Chen、Yong Lu、Ye Liu

  DOI：10.1007/s00706-022-03021-8

  日期：2023.2

  The structures of 2,5-diaryl-1,3,4-oxadiazoles with good stability have attract great attention for development of new and safe therapeutic agents with functions in antimicrobial, anti-inflammatory, antitumor, and antiviral (for treatment of HIV infection), etc. In the present work, over the developed Pd-catalytic system with involvement of the 3-thiophenyl-benzimidazolyl-based mono-phosphine, the

  2,5-二芳基-1,3,4-恶二唑的结构具有良好的稳定性，在开发具有抗菌、抗炎、抗肿瘤和抗病毒（用于治疗 HIV 感染）等功能的新型安全治疗剂方面备受关注)等。在目前的工作中，在开发的基于3-噻吩基-苯并咪唑基单膦的Pd催化体系上，芳基碘化物与酰基肼的一锅羰基化-脱水串联反应合成2， 5-diaryl-1,3,4-oxadiazoles 首次被报道，具有操作简单、效率高（产率62-93%）以及应用有机底物安全性高等优点。该串联反应需要140-160℃的相对较高的反应温度，其中所涉及的膦具有良好的稳定性和合适的立体电子特性，保证了该序列的完成。结果表明，芳基碘与酰肼的第一步羰基化反应N , N'-二芳基酰肼是整个过程中的决速步骤。随后，形成的N，N'-二苯甲酰肼在DCC等脱水剂存在下不可逆脱水成2,5-二芳基-1,3,4-恶二唑。 图形概要
• Photoredox/Cobalt-Catalyzed Cascade Oxidative Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles under Oxidant-Free Conditions
  作者：Jun-Li Li、Hao-Yuan Li、Shan-Shan Zhang、Shigang Shen、Xiu-Long Yang、Xiaoying Niu

  DOI：10.1021/acs.joc.3c01078

  日期：2023.11.3

  An efficient oxidant-free, photoredox-mediated cascade cyclization strategy for the synthesis of 1,3,4-oxadiazoles by using an organo acridinium photocatalyst and a cobaloxime catalyst has been developed. Various acylhydrazones have been transformed into the corresponding 1,3,4-oxadiazole products in up to 96% yield, and H2 is the only byproduct. Mechanistic experiments and density functional theory

  通过使用有机吖啶光催化剂和钴肟催化剂，开发了一种有效的无氧化剂、光氧化还原介导的级联环化策略，用于合成 1,3,4-恶二唑。各种酰腙已转化为相应的1,3,4-恶二唑产品，收率高达96%，H 2是唯一的副产物。机理实验和密度泛函理论 (DFT) 计算研究表明，光激发 Mes–Acr + *氧化以及去质子化产生的 π 自由基是以碳为中心的自由基，而不是以氧为中心的自由基，这是造成这种转变的原因。该方法的实用性突出是直接从市售醛和酰肼开始的一锅克级合成。
• 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。