3-(4-Fluoro-phenyl)-5-(4-methoxy-phenyl)-[1,2,4]oxadiazole | 221348-21-6

• 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-(4-Fluoro-phenyl)-5-(4-methoxy-phenyl)-[1,2,4]oxadiazole
• 英文别名: 3-(4-Fluorophenyl)-5-(4-methoxyphenyl)-1,2,4-oxadiazole
• CAS: 221348-21-6
• 化学式: C₁₅H₁₁FN₂O₂
• 分子量: 270.263
• InChiKey: IGBKOUUETRPSCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  48.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Fluoro-phenyl)-5-(4-methoxy-phenyl)-[1,2,4]oxadiazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4-[3-(4-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-phenol
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3,5-diarylisoxazoles and 3,5-diaryl-1,2,4-oxadiazoles, novel classes of small molecule interleukin-8 (IL-8) receptor antagonists

  摘要：

  A novel series of 3,5-diarylisoxazole and 3,5-diaryl-1,2,4-oxadiazole IL-8 antagonists has been identified. These compounds exhibit activity in an IL-8 binding assay as well as in a functional assay of IL-8 induced elastase release from neutrophils. In addition, one of the compounds exhibits oral activity in a rat adjuvant arthritis model. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.080
• 作为产物：
  描述：

  4-氟苯甲酰胺肟 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.02h， 生成 3-(4-Fluoro-phenyl)-5-(4-methoxy-phenyl)-[1,2,4]oxadiazole
  参考文献：
  名称：

  使用改进的基于铀的活化从羧酸并行合成1,2,4-恶二唑

  摘要：

  我们描述了使用2-（1 H-苯并三唑-1-基）-1,1,3,3-四甲基脲四氟硼酸酯（TBTU）作为羧酸的活化剂，由羧酸和a胺肟合成1,2,4-恶二唑。O-酰化步骤的羧酸官能团。该方法用于合成24个1,2,4-恶二唑的文库。

  DOI：

  10.1016/s0040-4039(00)02293-0

文献信息

• 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％）。
• 一种3,5-二取代1,2,4-噁二唑的合成方法
  申请人：江苏食品药品职业技术学院

  公开号：CN112979573A

  公开（公告）日：2021-06-18

  本发明涉及一种新的合成3，5‑二取代‑1，2，4‑噁二唑的合成方法。本发明的方法具有在室温下反应，通过一锅法高产率合成1，2，4‑噁二唑且最终产物无需通过柱层析的特点。本发明合成的3，5‑二取代‑1，2，4‑噁二唑可以用于医疗领域。
• Parallel synthesis of 1,2,4-oxadiazoles using CDI activation
  作者：Tracy L Deegan、Theodore J Nitz、Diane Cebzanov、Denise E Pufko、John A Porco

  DOI：10.1016/s0960-894x(98)00712-4

  日期：1999.1

  1,2,4-Oxadiazoles have been prepared in parallel using 1,1'-carbonyldiimidazole (CDI) as a reagent for both formation and cyclodehydration of O-acyl benzamidoximes. The use of CDI facilitates parallel purification of the oxadiazole products by simple liquid-liquid extraction and filtration. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A Preferred Synthesis of 1,2,4‐Oxadiazoles
  作者：Brenda Pipik、Guo‐Jie Ho、J. Michael Williams、David A. Conlon

  DOI：10.1081/scc-120034169

  日期：2004.12.31

  An efficient and high-yielding one-pot synthesis of 1,2,4-oxadiazoles from carboxylic acids and amidoximes is described. Activation of the carboxylic acid using hydroxybenzotriazole (HOBt) and EDC/HCl followed by reaction with an amidoxime generates an oxime ester. Without isolation, the oxime ester is dehydrated to give the oxadiazole ring.
• Synthesis and structure–activity relationships of 3,5-diarylisoxazoles and 3,5-diaryl-1,2,4-oxadiazoles, novel classes of small molecule interleukin-8 (IL-8) receptor antagonists
  作者：Michele A Weidner-Wells、Todd C Henninger、Stephanie A Fraga-Spano、Christine M Boggs、Michele Matheis、David M Ritchie、Dennis C Argentieri、Michael P Wachter、Dennis J Hlasta

  DOI：10.1016/j.bmcl.2004.05.080

  日期：2004.8

  A novel series of 3,5-diarylisoxazole and 3,5-diaryl-1,2,4-oxadiazole IL-8 antagonists has been identified. These compounds exhibit activity in an IL-8 binding assay as well as in a functional assay of IL-8 induced elastase release from neutrophils. In addition, one of the compounds exhibits oral activity in a rat adjuvant arthritis model. (C) 2004 Elsevier Ltd. All rights reserved.