2-butyl-5-phenyl-1,3,4-oxadiazole

• 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-butyl-5-phenyl-1,3,4-oxadiazole
• 英文别名: 5-Butyl-2-phenyl-1,3,4-oxadiazole
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: TUNZZQHAOUISPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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'-[(1E)-pentylidene]benzohydrazide 以70%的产率得到
  参考文献：
  名称：

  Yang Rui-Yang, Dai Li-Xin, J. Org. Chem., 58 (1993) N 12, S 3381-3383

  摘要：

  DOI：

文献信息

• 1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis
  作者：Sara Cesarini、Nicoletta Colombo、Maurizio Pulici、Eduard R. Felder、Wolfgang K.-D. Brill

  DOI：10.1016/j.tet.2006.08.016

  日期：2006.10

  Oxadiazoles were generated upon a dehydrative cyclization reaction with 2-acyl hydrazides bound to the polymeric support via one of their N atoms using TFAA as a dehydration agent.

  使用TFAA作为脱水剂，通过与2-酰基酰肼通过其N原子之一结合到聚合物载体上的脱水环化反应，生成恶二唑。
• 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。
• Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation–cyclization of hydrazides and diketones
  作者：Pinhui Diao、Yanqin Ge、Wenpei zhang、Chen Xu、Nannan Zhang、Cheng Guo

  DOI：10.1016/j.tetlet.2018.01.037

  日期：2018.2

  A visible-light-induced synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from simple diketones and hydrazides with the assistant of the photocatalyst eosin Y catalyzed decarboxylation and cyclization under mild conditions has been discovered. The reaction tolerates a wide range of functional groups and gives a variety of valuable 1,3,4-oxadiazoles in moderate to good yields. Finally, a plausible reaction

  发现了在光催化条件下，由简单的二酮和酰肼在光催化曙红Y的催化下可见光诱导的2,5-二取代的1,3,4-恶二唑的合成。该反应可耐受各种官能团，并以中等至良好的收率得到各种有价值的1,3,4-恶二唑。最后，提出了合理的反应机理。
• Green oxidative cyclization to access 2,5-disubstituted-1,3,4-oxadiazoles from aldehydes and hydrazide derivatives using FeBr3 catalyst and hydrogen peroxide
  作者：Jian Wang、Linyang Wang、Huilin Qin、Ruotong Tian、Yuliang Pan

  DOI：10.1016/j.tetlet.2023.154783

  日期：2023.11

  2,5-disubstituted-1,3,4-oxadiazoles Oxidative cyclization of aldehydes and hydrazide derivatives to access 2,5-disubstituted-1,3,4-oxadiazoles has been developed using a catalytic amount of FeBr3 in the presence of aqueous hydrogen peroxide as an oxidant. By synthesizing 35 examples of 2,5-disubstituted 1,3,4-oxadiazoles, this approach was demonstrated to have good features including broad scope, mild

  2,5-二取代-1,3,4-恶二唑已开发出在水溶液存在下使用催化量的 FeBr 3将醛和酰肼衍生物氧化环化以获得 2,5-二取代-1,3,4-恶二唑过氧化氢作为氧化剂。通过合成35个2,5-二取代1,3,4-恶二唑实例，证明该方法具有适用范围广、条件温和、耐空气/水、操作简单等优点。更重要的是，它有望在有机合成中得到广泛的应用。
• Hypervalent iodine oxidation of N-acylhydrazones and N-phenylsemicarbazone: an efficient method for the synthesis of derivatives of 1,3,4-oxadiazoles and .DELTA.3-1,3,4-oxadiazolines
  作者：Ruiyang Yang、Lixin Dai

  DOI：10.1021/jo00064a027

  日期：1993.6

  The oxidation of ketone N-acylhydrazones 1 by phenyliodine(III) diacetate (PIDA) in alcohol gave 2-alkoxy-DELTA3-1,3,4-oxadiazolines 4 in excellent yields, while the oxidative cyclization of aldehyde N-acylhydrazone 2 by PIDA in methanolic sodium acetate gave 2,5-disubstituted 1,3,4-oxadiazoles in good yields. The oxidation of acetone 4-phenylsemicarbazone afforded 2-(N-phenylimino)-DELTA3-1,3,4-oxadiazoline in excellent yield.