2-(4-chlorophenyl)-5-ethyl-[1,3,4]oxadiazole | 41420-98-8

• 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-(4-chlorophenyl)-5-ethyl-[1,3,4]oxadiazole
• 英文别名: 2-(4-chlorophenyl)-5-ethyl-1,3,4-oxadiazole；2-(4-chloro-phenyl)-5-ethyl-[1,3,4]oxadiazole；ethyl-(4-chloro-phenyl)-[1,3,4]oxadiazole；Aethyl-(4-chlor-phenyl)-[1,3,4]oxadiazol
• CAS: 41420-98-8
• 化学式: C₁₀H₉ClN₂O
• mdl: MFCD11094163
• 分子量: 208.647
• InChiKey: IAFKLLVLMSJCAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  4-氯苯甲酰肼 在 tert-Butyl hypoiodite 、 碳酸二甲酯 作用下， 以 乙醇 为溶剂， 反应 10.25h， 生成 2-(4-chlorophenyl)-5-ethyl-[1,3,4]oxadiazole
  参考文献：
  名称：

  在中性条件下使用 t-BuOI 合成 2,5-二取代 1,3,4-恶二唑的 N-酰基腙的有效氧化环化

  摘要：

  摘要 利用由 t-BuOCl 和 NaI 原位生成的次碘酸叔丁酯 (t-BuOI) 开发了一种有效的 N-酰基腙氧化环化方法。在短时间内以高产率合成了多种 2,5-二取代 1,3,4-恶二唑。该方法也适用于杂环醛和脂肪醛衍生的N-酰基腙的环化。温和的反应条件和简单的后处理操作使该程序成为合成 2,5-二取代 1,3,4-恶二唑的良好替代方法。

  DOI：

  10.1515/hc-2012-0179

文献信息

• Oxadiazoles in Medicinal Chemistry
  作者：Jonas Boström、Anders Hogner、Antonio Llinàs、Eric Wellner、Alleyn T. Plowright

  DOI：10.1021/jm2013248

  日期：2012.3.8

  replacements for ester and amide functionalities. The current study presents a systematic comparison of 1,2,4- and 1,3,4-oxadiazole matched pairs in the AstraZeneca compound collection. In virtually all cases, the 1,3,4-oxadiazole isomer shows an order of magnitude lower lipophilicity (log D), as compared to its isomeric partner. Significant differences are also observed with respect to metabolic stability

  恶二唑是含有两个碳，两个氮和一个氧原子的五元杂芳族环，它们以不同的区域异构形式存在。恶二唑是类药物分子中经常出现的基序，经常使用它们作为酯和酰胺官能团的生物等位替代物。当前的研究提出了阿斯利康化合物集合中1,2,4-和1,3,4-恶二唑匹配对的系统比较。在几乎所有情况下，1,3,4-恶二唑异构体的亲脂性均降低一个数量级（对数D），与其同分异构的合作伙伴相比。在代谢稳定性，hERG抑制和水溶性方面也观察到显着差异，有利于1,3,4-恶二唑异构体。1,2,4和1,3,4区域异构体之间的轮廓差异可以通过其本质上不同的电荷分布（例如，偶极矩）来合理化。为了促进这些杂芳族环的使用，描述了在温和条件下易于获得广谱的1,3,4-恶二唑的新颖合成途径。
• Efficient synthesis of 1,3,4-oxadiazoles promoted by NH4Cl
  作者：Krishna Kumar Gnanasekaran、Baskar Nammalwar、Maeghan Murie、Richard A. Bunce

  DOI：10.1016/j.tetlet.2014.10.028

  日期：2014.12

  An efficient and inexpensive approach to the synthesis of 2-substituted and 2,5-disubstituted 1,3,4-oxadiazoles from arylhydrazides and orthoesters is reported using catalytic NH4Cl. The conditions are mild, and thus, compatible with a variety of functional groups. The optimized reaction is performed using 30 mol % of NH4Cl in 100% EtOH and is generally complete within I h for non-aromatic orthoesters and 2-10 h for aromatic orthoesters. The reaction permits both electron-releasing and electron-withdrawing groups on the arylhydrazide substrate. Most products are formed in high yields and require only minimal purification. Compared with earlier reports, the current reactions proceed in shorter time and require less of the orthoester. (C) 2014 Elsevier Ltd. All rights reserved.
• Silica Sulfuric Acid: An Efficient and Versatile Acidic Catalyst for the Rapid and Ecofriendly Synthesis of 1,3,4‐Oxadiazoles at Ambient Temperature
  作者：Minoo Dabiri、Peyman Salehi、Mostafa Baghbanzadeh、Mohammad Ali Zolfigol、Mahboobeh Bahramnejad

  DOI：10.1080/00397910701199151

  日期：2007.4.1

  A rapid and green synthesis of 2,5-disubstituted 1,3,4-oxadiazoles is reported. The title compounds were prepared by the reaction of different acyl hydrazides and orthoesters in the presence of silica sulfuric acid under solvent-free conditions. In this new process, reactions were run at ambient temperature and completed in a short period of time with high yields.
• Alum (KAl(SO4)2 · 12H2O): An Efficient and Inexpensive Catalyst for the One-pot Synthesis of 1,3,4-Oxadiazoles under Solvent-Free Conditions
  作者：Minoo Dabiri、Peyman Salehi、Mostafa Baghbanzadeh、Mahboobeh Bahramnejad

  DOI：10.1007/s00706-007-0724-0

  日期：2007.12

  Alum (KAl(SO4)(2) center dot 12H(2)O) catalyzed the efficient synthesis of mono- and disubstituted 1,3,4-oxadiazoles by the condensation of acyl hydrazides with orthoesters under solvent-free conditions at 100 degrees C. This methodology offers significant improvements for the synthesis of oxadiazoles with regard to the yield of products, simplicity in operation, inexpensive reagents, and green aspects by avoiding toxic catalysts and solvents.
• US7262212B2
  申请人：——

  公开号：US7262212B2

  公开（公告）日：2007-08-28