5-(furan-2-yl)-3-phenyl-1,2,4-oxadiazole | 309734-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(furan-2-yl)-3-phenyl-1,2,4-oxadiazole
• CAS: 309734-72-3
• 化学式: C₁₂H₈N₂O₂
• mdl: MFCD01882751
• 分子量: 212.208
• InChiKey: AINKNWCODGPLKV-UHFFFAOYSA-N

物化性质

• 沸点：
  359.9±34.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 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：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(furan-2-yl)-3-phenyl-4,5-dihydro-1,2,4-oxadiazole 在 糠醛 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 21.0h， 以125 mg的产率得到5-(furan-2-yl)-3-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes in the Superbasic System NaOH/DMSO

  摘要：

  A new procedure has been proposed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with aldehydes in the superbasic system NaOH/DMSO at room temperature. The scope of the proposed procedure has been demonstrated by 15 syntheses from various amidoximes and aromatic aldehydes with 27-76% yields. The procedure is inapplicable to aliphatic aldehydes.

  DOI：

  10.1134/s107042802007009x

文献信息

• A convenient and mild method for 1,2,4-oxadiazole preparation: cyclodehydration of O -acylamidoximes in the superbase system MOH/DMSO
  作者：Sergey Baykov、Tatyana Sharonova、Angelina Osipyan、Sergey Rozhkov、Anton Shetnev、Alexey Smirnov

  DOI：10.1016/j.tetlet.2016.05.071

  日期：2016.6

  Herein, we reported a general, convenient, and efficient synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO (M = Li, Na, K). Excellent isolated yields (up to 98%) were attained within short reaction times (10–20 min). In addition, mild reaction conditions and a simple work-up procedure allow the synthesis of a wide range of heat-labile

  在本文中，我们报道了在超碱系统MOH / DMSO（M = Li，Na，K）中通过O-酰基酰胺基肟的环脱水作用，一种一般，便捷，有效的合成3,5-二取代-1,2,4-恶二唑的方法。在较短的反应时间内（10-20分钟）即可获得出色的分离产率（高达98％）。此外，温和的反应条件和简单的后处理程序可以合成多种热不稳定的含1,2,4-恶二唑的物质。
• The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters
  作者：Sergey Baykov、Tatyana Sharonova、Anton Shetnev、Sergey Rozhkov、Stanislav Kalinin、Alexey V. Smirnov

  DOI：10.1016/j.tet.2017.01.007

  日期：2017.2

  The first one-pot room-temperature protocol for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via the condensation between amidoximes and carboxylic acid esters in superbase medium MOH/DMSO is reported. A broad spectrum of alkyl, aryl and hetaryl amidoximes and esters was examined. This reaction route provides convenient access to 1,2,4-oxadiazoles, which is highly desirable because in the light

  据报道，第一个单锅室温规程是通过在超碱性介质MOH / DMSO中通过a肟和羧酸酯之间的缩合反应合成3,5-二取代-1,2,4-恶二唑。检查了烷基，芳基和杂芳基肟和酯的广谱光谱。该反应途径提供了方便地获得1,2,4-恶二唑的途径，这是非常需要的，因为鉴于这种特权支架，公认其是新型治疗剂和高科技材料设计的重要核心。
• NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N‒O bond formation
  作者：Ertong Li、Manman Wang、Zhen Wang、Wenquan Yu、Junbiao Chang

  DOI：10.1016/j.tet.2018.07.036

  日期：2018.8

  A reaction involving an efficient NBS-mediated oxidative N‒O bond formation has been established for the synthesis of 1,2,4-oxadiazoles from readily accessible N-acyl amidines. The features of this synthetic method include simplicity of operation, mild reaction conditions, short reaction times, high yields, and eco-friendliness. The reaction also works well with crude N-acyl amidines obtained by amidation

  已经建立了涉及有效的NBS介导的氧化N ＝ O键形成的反应，用于由容易获得的N-酰基am合成1,2,4-恶二唑。这种合成方法的特点包括操作简单，反应条件温和，反应时间短，产率高和环保。该反应还适用于通过简单的苯甲酸和mid酰胺化而获得的粗制N-酰基s，以可扩展的方式生产生物学上相关的1,2,4-恶二唑。
• Base-mediated one-pot synthesis of 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride without addition of extra oxidant
  作者：Wei Wang、Hao Xu、Yuanqing Xu、Tao Ding、Wenkai Zhang、Yanrong Ren、Haibo Chang

  DOI：10.1039/c6ob01794k

  日期：——

  A simple base-mediated one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride has been developed, in which the aldehydes act as both substrates and oxidants. The reactions include three sequential procedures: base-promoted intermolecular addition of hydroxylamine to nitrile to lead to amidoxime, treatment of the amidoxime with an aldehyde to

  已经开发了由腈，醛和盐酸羟胺形成的简单的碱介导的一锅法合成3,5-二取代的1,2,4-恶二唑，其中醛既充当底物又充当氧化剂。反应包括三个顺序程序：碱促进的羟胺分子间加成到腈中以生成a胺肟；用醛处理the胺肟以形成4,5-二氢-1,2,4-恶二唑；以及氧化4， 5-二氢-1,2,4-恶二唑通过使用另一种醛得到1,2,4-恶二唑。该方法代表了合成3,5-二取代的1,2,4-恶二唑的直接而简单的方法。
• Compostions and Methods for Controlling Nematodes
  申请人：Williams Deryck J.

  公开号：US20090048311A1

  公开（公告）日：2009-02-19

  Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.

  本文描述了用于控制线虫的组合物和过程，例如侵害植物或动物的线虫。这些化合物包括噁唑、噁二唑和噻二唑。