2-cyclohexyl-5-phenyl-1,3,4-oxadiazole | 92492-51-8

• 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-cyclohexyl-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-cyclohexyl-5-phenyl-[1,3,4]oxadiazole；2-Cyclohexyl-5-phenyl-1,3,4-oxadiazol；2-Cyclohexyl-5-phenyl-1,3,4-oxdiazol；2-Phenyl-5-cyclohexyl-1,3,4-oxdiazol
• CAS: 92492-51-8
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: ZNYUIVVJRHPTGM-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  371.9±25.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  环己甲酰氯 在 溶剂黄146 、 三乙胺 、 ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 2-cyclohexyl-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using [Et₂NSF₂]BF₄as a practical cyclodehydration agent

  摘要：

  报道了使用XtalFluor-E（[Et2NSF2]BF4）作为环脱水剂，从1,2-二酰基肼制备1,3,4-噁二唑的方法。合成了多种功能化的1,3,4-噁二唑，并发现使用乙酸作为添加剂通常能提高产率。

  DOI：

  10.1039/c1ob06512b

文献信息

• Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion
  作者：Xiang-Yuan Fan、Xiao Jiang、Ying Zhang、Zhen-Bang Chen、Yong-Ming Zhu

  DOI：10.1039/c5ob01328c

  日期：——

  An efficient one-pot palladium-catalyzed reaction for the synthesis of diazoles from readily available hydrazides and aryl halide via isocyanide insertion/cyclization sequence has been developed.

  已经开发出一种高效的钯催化的单锅反应，用于从易于获得的肼酯和芳基卤化物通过异氰插入/环化序列合成哒唑。

• 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。
• Ligand-free Cu(<scp>ii</scp>)-mediated aerobic oxidations of aldehyde hydrazones leading to N,N′-diacylhydrazines and 1,3,4-oxadiazoles
  作者：Lei Liu、Suliu Feng

  DOI：10.1039/c7ob00042a

  日期：——

  A Cu(II)-mediated synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles from aldehyde hydrazones has been developed. This is the first time that the synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles using N,N-dimethylamides as the acylation reagent and O2 in air as the oxidation reagent is reported. These reactions offered several advantages including simple workups, ligand-free inexpensive

  已开发了一种由Cu（II）介导的从醛中合成N，N'-二酰基肼和1,3,4-恶二唑的方法。这是第一次发现的合成Ñ，Ñ使用'-diacylhydrazines和1,3,4-恶二唑Ñ，Ñ -dimethylamides，作为酰化试剂和O 2在空气作为氧化试剂的报道。这些反应提供了几个优点，包括简单的后处理，无配体的廉价金属盐作为介体，高收率和广泛的底物范围。
• Iodine-catalysed oxidative cyclisation of acylhydrazones to 2,5-substituted 1,3,4-oxadiazoles
  作者：Ganesh Majji、Saroj Kumar Rout、Srimanta Guin、Anupal Gogoi、Bhisma K. Patel

  DOI：10.1039/c3ra44897e

  日期：——

  An environmentally benign synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed starting from N-aroylhydrazones and N-acetylhydrazones at room or ambient temperature using a catalytic quantity of iodine in the presence of an aqueous hydrogen peroxide oxidant.

  在室温或环境温度下，在过氧化氢水溶液的存在下，使用催化量的碘，从N-芳酰基yl和N-乙酰hydr开始，开发了一种环境友好的2,5-二取代的1,3,4-恶二唑合成方法。
• 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。