3,5-bis(4-fluorophenyl)-1,2,4-oxadiazole | 330830-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-bis(4-fluorophenyl)-1,2,4-oxadiazole
• CAS: 330830-97-2
• 化学式: C₁₄H₈F₂N₂O
• 分子量: 258.227
• InChiKey: LXKFHRLJFJSYDE-UHFFFAOYSA-N

物化性质

• 沸点：
  369.1±52.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 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：
  38.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-bis(4-fluorophenyl)-1,2,4-oxadiazole 、 咔唑 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以81.2%的产率得到3,5-bis(4-(9H-carbazol-9-yl)phenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of new bipolar host materials based on 1,2,4-oxadiazole for blue phosphorescent OLEDs

  摘要：

  Two novel bipolar host materials, namely 3,5-bis(4-(9H-carbazol-9-yl)pheny1)-1,2,4-oxadiazole (pCzmOXD) and 3,5-bis(3-(9H-carbazol-9-yl)pheny1)-1,2,4-oxadiazole (mCzmOXD) were designed and synthesized, by incorporating a new block 1,2,4-oxadiazole as the n-type moiety and changing its linking pattern with carbazole. As expected, high triplet energy (over 2.81 eV) for mCzmOXD was achieved due to the intrinsic meta-linkage of 1,2,4-oxadiazole. When both materials were applied in blue phosphorescent organic light-emitting diodes, good performance of 13.0 cd A(-1)/16.0 cd A(-1) were achieved for pCzmOXD and mCzmOXD in iridium(III) bis[(4, 6 - difluorophenyl)pyridinato - N, C-2'] picolinate (Flrpic)-based devices, respectively. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.09.029
• 作为产物：
  描述：

  4-氟苯甲酰胺肟 在 咪唑盐酸盐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以49%的产率得到3,5-bis(4-fluorophenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  咪唑盐酸盐促进 3,5-二取代-1,2,4-恶二唑的合成

  摘要：

  咪唑盐酸盐作为添加剂促进酰胺肟和 DMA 衍生物反应生成 3,5-二取代-1,2,4-恶二唑，收率从低到高，无需使用偶联剂、氧化剂、强酸或强碱和其他添加剂。

  DOI：

  10.1016/j.tet.2021.132496

文献信息

• Improved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-oxadiazol-5-yl)propionic Acids and Their Larvicidal and Fungal Growth Inhibitory Properties
  作者：Ricardo Antonio Wanderley Neves Filho、Cecília Aguiar da Silva、Clécia Sipriano Borges da Silva、Vanessa Passos Brustein、Daniela Maria do Amaral Ferraz Navarro、Fábio André Brayner dos Santos、Luiz Carlos Alves、Marília Gabriela dos Santos Cavalcanti、Rajendra Mohan Srivastava、Maria das Graças Carneiro-Da-Cunha

  DOI：10.1248/cpb.57.819

  日期：——

  The synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids from arylamidoximes and succinic anhydride under focused microwave irradiation conditions is described. The new synthetic method furnished the desired products in 2-3 min and good yields. Furthermore, the previously complicated purification procedure has been simplified in a manner which is quick, eco-friendly and cost-effective. Larvicidal

  描述了在聚焦微波辐射条件下由芳基嘧啶和琥珀酸酐合成3-（3-芳基-1,2,4-恶二唑-5-基）丙酸。新的合成方法可在2-3分钟内提供所需的产品，并具有良好的产量。此外，先前复杂的纯化过程已经以快速，环保和成本有效的方式得到简化。使用几种3-（3-芳基-1,2,4-恶二唑-5-基）丙酸进行了杀幼虫的生物测定和真菌生长抑制试验。这些酸对埃及伊蚊的L4幼虫具有很强的杀幼虫活性。结果表明，杀幼虫活性可能与除氟原子以外的苯环对位的吸电子取代基的存在有关。在幼虫生物测定中，1,2,4-恶二唑在虹吸管和肛门乳头的幼虫螺旋瓣中观察到的变化是幼虫死亡的原因。此外，在初步评估中，所有酸均抑制了五种不同类型的真菌（即镰刀镰刀菌，尖孢镰刀菌，念珠形镰刀菌，十二指肠球菌和红曲霉）的真菌生长。这两个活性都首次公开了在丙酸的C-3处连接的1,2,4-恶二唑-5-基环。
• Potassium Poly(Heptazine Imide): Transition Metal‐Free Solid‐State Triplet Sensitizer in Cascade Energy Transfer and [3+2]‐cycloadditions
  作者：Aleksandr Savateev、Nadezda V. Tarakina、Volker Strauss、Tanveer Hussain、Katharina Brummelhuis、José Manuel Sánchez Vadillo、Yevheniia Markushyna、Stefano Mazzanti、Alexander P. Tyutyunnik、Ralf Walczak、Martin Oschatz、Dirk M. Guldi、Amir Karton、Markus Antonietti

  DOI：10.1002/anie.202004747

  日期：2020.8.24

  Polymeric carbon nitride materials have been used in numerous light‐to‐energy conversion applications ranging from photocatalysis to optoelectronics. For a new application and modelling, we first refined the crystal structure of potassium poly(heptazine imide) (K‐PHI)—a benchmark carbon nitride material in photocatalysis—by means of X‐ray powder diffraction and transmission electron microscopy. Using

  聚合氮化碳材料已用于从光催化到光电子学的众多光能转换应用中。对于新的应用和建模，我们首先通过 X 射线粉末衍射和透射电子显微镜精炼了聚庚嗪酰亚胺钾 (K-PHI)（光催化领域的基准氮化碳材料）的晶体结构。利用 K-PHI 的晶体结构，进行周期性 DFT 计算，以计算态密度 (DOS) 并定位带内态 (IBS)。研究发现 IBS 负责增强近红外区域的 K-PHI 吸收，充当电子陷阱，并可用于能量转移反应。一旦被可见光激发，氮化碳除了直接复合之外，还可以发生单线态-三线态系间窜越。我们利用以 K-PHI 为中心的三重激发态来触发一系列能量转移反应，进而敏化单线态氧 ( 1 O 2 ) 作为起点，合成多达 25 种不同的富氮杂环。
• One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Directly from Nitrile and Hydroxylamine Hydrochloride Under Solvent-Free Conditions Using Potassium Fluoride as Catalyst and Solid Support
  作者：Shahnaz Rostamizadeh、Hamid Reza Ghaieni、Reza Aryan、Ali-Mohammad Amani

  DOI：10.1080/00397910903370642

  日期：2010.9.20

  A one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles with two identical substituents directly from the reaction of nitriles and hydroxylamine hydrochloride in the presence of potassium fluoride as catalyst and solid support under solvent-free condition is described. Moreover, the formation of products has been discussed, and a plausible mechanism has been presented. Simplicity of the process

  描述了在无溶剂条件下，在氟化钾作为催化剂和固体载体存在下，腈和盐酸羟胺反应直接合成具有两个相同取代基的 3,5-二取代 1,2,4-恶二唑。此外，还讨论了产物的形成，并提出了一个合理的机制。该方法的一些优点是过程简单、在水性介质中后处理和出色的收率。
• Highly Efficient One-Pot Preparation of 1,2,4-Oxadiazoles in the Presence of Diazabicycloundecene
  作者：Kirill Lukin、Vimal Kishore

  DOI：10.1002/jhet.1689

  日期：2014.1

  New highly efficient method for the cyclization of acylamidoximes in the presence of diazabicycloundecene was developed and incorporated into a general and practical one‐pot synthesis of 1,2,4‐oxadiazoles (11 examples, 85–97% yields).

  开发了一种新的高效方法，可在存在二氮杂双环十一碳烯的情况下环化酰肟类环化反应，并将其纳入一般和实用的1,2,4-恶二唑单锅合成中（11个实例，产率为85-97％）。
• Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles
  作者：Xuetong Wang、Yin Wang、Xiaoling Liu、Tingshu He、Lingli Li、Huili Wu、Shangjun Zhou、Dan Li、Siwei Liao、Ping Xu、Xing Huang、Jianyong Yuan

  DOI：10.1016/j.tet.2021.132496

  日期：2021.11

  Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.

  咪唑盐酸盐作为添加剂促进酰胺肟和 DMA 衍生物反应生成 3,5-二取代-1,2,4-恶二唑，收率从低到高，无需使用偶联剂、氧化剂、强酸或强碱和其他添加剂。