5-phenyl-N-p-tolyl-1,3,4-oxadiazol-2-amine | 1617-95-4

• 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: 5-phenyl-N-p-tolyl-1,3,4-oxadiazol-2-amine
• 英文别名: N-(4-methylphenyl)-5-phenyl-1,3,4-oxadiazol-2-amine
• CAS: 1617-95-4
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: DOMYDIWFOBBDCI-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C(Solv: ethanol (64-17-5); benzene (71-43-2))
• 沸点：
  407.9±38.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 5-phenyl-N-p-tolyl-1,3,4-oxadiazol-2-amine 生成 4-methyl-N-(5-phenyl-[1,3,4]oxadiazol-2-yl)-N-4-methylbenzenesulfonamide
  参考文献：
  名称：

  The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating

  摘要：

  Herein, we report on the preparation of a library of 5-substituted-2-amino-1,3,4-oxadiazoles and the corresponding thiadiazole analogues. Presented is a one-pot preparation of the 2-ammosulfonylated analogues through a three component coupling of an acylhydrazine, an isocyanate and sulfonyl chloride promoted by a polymer-supported phosphazine base under microwave dielectric heating. Also described is the optimization process and details pertaining to the elucidation of the reaction products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.062
• 作为产物：
  描述：

  3-(苯甲酰基氨基)-1-(4-甲基苯基)硫脲 在 potassium hydrogensulfate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 5-phenyl-N-p-tolyl-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  KHSO4 介导的 2-amino-1,3,4-oxadiazole 衍生物的简易合成

  摘要：

  通过苯甲酰肼和异硫氰酸酯衍生物的环化脱硫，建立了一种新型、高效且温和的 KHSO 4介导的 2-氨基-1,3,4-恶二唑合成方法。反应在室温下顺利进行，并以中等至良好的收率产生相应的产物。该协议还显示出良好的官能团耐受性。

  DOI：

  10.1016/j.tet.2021.132382

文献信息

• Desulfurization Strategy in the Construction of Azoles Possessing Additional Nitrogen, Oxygen or Sulfur using a Copper(I) Catalyst
  作者：Srimanta Guin、Saroj Kumar Rout、Anupal Gogoi、Shyamapada Nandi、Krishna Kanta Ghara、Bhisma K. Patel

  DOI：10.1002/adsc.201200408

  日期：2012.10.8

  A tandem and convergent approach to various N-, O-, or S-containing azoles has been developed by exploiting the thiophilic property of copper(I) iodide used in a catalytic quantity. The present protocol gives access to amino-substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter- or intramolecular attack of suitable

  通过利用催化量使用的碘化亚铜（I）的亲硫特性，已经开发出一种串联和收敛的方法，用于处理各种含N，O或S的唑。本方案通过其各自前体的氧化脱硫，然后通过分子间或分子内攻击合适的亲核试剂，来获得氨基取代的四唑，三唑，恶二唑和噻二唑。对于氨基四唑和三唑，可通过适当调节pK a获得出色的区域选择性与不对称硫脲连接的母体胺的分子量 该方法代表了一种自动催化过程，其中碘化铜（I）被转化为硫化铜（II），硫化铜又转化为活性的氧化铜（II），有效地推进了催化循环。还使用扫描电子显微镜（SEM）和能量色散X射线光谱（EDS）分析研究了铜催化剂的命运，从而深入了解了该催化过程的机理。
• 15N NMR study of substituted 2-(phenylamino)-5-phenyl-1,3,4-oxadiazoles
  作者：Błażej Gierczyk、Barbara Nowak-Wydra、Jakub Grajewski、Maciej Zalas

  DOI：10.1002/mrc.1928

  日期：2007.2

  Substituted 2‐(phenylamino)‐5‐phenyl‐1,3,4‐oxadiazoles were studied by 15N NMR spectroscopy. All signals were assigned on the basis of HMQC and HMBC experiments. Chemical shifts values were correlated with empirical Hammett parameters as well as with calculated electron densities and chemical shieldings. Copyright © 2006 John Wiley & Sons, Ltd.

  通过 15N NMR 光谱研究取代的 2-(苯基氨基)-5-苯基-1,3,4-恶二唑。所有信号均基于 HMQC 和 HMBC 实验分配。化学位移值与经验哈米特参数以及计算的电子密度和化学屏蔽相关。版权所有 © 2006 John Wiley & Sons, Ltd.
• A new and efficient synthesis of 1,3,4-oxadiazole derivatives using TBTU
  作者：Shokoofeh Maghari、Sorour Ramezanpour、Fatemeh Darvish、Saeed Balalaie、Frank Rominger、Hamid Reza Bijanzadeh

  DOI：10.1016/j.tet.2012.11.071

  日期：2013.2

  An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from isothiocyanates and hydrazides through cyclodesulfurization in the presence of (O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate) TBTU as an uronium coupling reagent has been developed. The present methodology offers several advantages, such as simple and easy work-up procedures, mild reaction conditions

  用于从异硫氰酸酯和酰肼2,5-二取代的1,3,4-恶二唑，通过环化脱硫中的（存在下合成的有效方法Ô（苯并三唑-1-基） - - ñ，Ñ，N' ，N' -已经开发出四甲基脲鎓四氟硼酸酯（TBTU）作为铀偶联剂。本方法具有几个优点，例如简单和容易的后处理程序，温和的反应条件，并且对环境无害。
• Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles
  作者：Eugene L. Piatnitski Chekler、Hassan M. Elokdah、John Butera

  DOI：10.1016/j.tetlet.2008.09.057

  日期：2008.11

  A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R-1 and R-2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented. (c) 2008 Elsevier Ltd. All rights reserved.