5-pentadecyl-3-(p-tolyl)-1,2,4-oxadiazole | 872177-47-4

• 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-pentadecyl-3-(p-tolyl)-1,2,4-oxadiazole
• 英文别名: 3-(4-Methylphenyl)-5-pentadecyl-1,2,4-oxadiazole
• CAS: 872177-47-4
• 化学式: C₂₄H₃₈N₂O
• 分子量: 370.579
• InChiKey: LZYYRHMQJWLDLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  反应 6.0h， 以74.4%的产率得到5-pentadecyl-3-(p-tolyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 3-aryl-5-decapentyl-1,2,4-oxadiazoles possessing antiinflammatory and antitumor properties

  摘要：

  A simple, convenient and straightforward synthesis of 3-aryl-1,2,4-oxadiazoles 4a-f from arylamidoximes 1a-f and palmitic acid 2 is described. Compounds 4a-f are non-lethal in mice at four times the therapeutic dose (i.p., LD50>1 g kg(-1) of the animals' body weight). These heterocycles have been found to possess antiinflammatory property similar to aspirin and ibuprofen. Three compounds, viz., 4a, d, e have also been evaluated for antitumor activity, where 4d exhibited an excellent activity comparable to lapachol.

  DOI：

  10.1016/j.farmac.2005.08.003

文献信息

• A new method to synthesize 1,2,4-oxadiazoles by using DMTMM as condensing agent
  作者：Yijie Wang、Xu Cheng、Jing Xu、Lin Wang、Shouguo Zhang、Shuchen Liu、Tao Peng

  DOI：10.1016/j.tetlet.2023.154590

  日期：2023.7

  condensing agent for synthesis of 1,2,4-oxadiazoles from corresponding carboxylic acids and amidoximes in the mixed solvent of THF and NMP. First, carboxylic acids were activated by DMTMM, and then reacted with amidoximes to convert to O-acylated amidoximes. The unusual solvent system THF-NMP successfully promoted dehydration process of O-acylated amidoximes and 1,2,4-oxadiazoles were acquired in one-pot

  DMTMM作为缩合剂在THF和NMP的混合溶剂中由相应的羧酸和偕胺肟合成1,2,4-恶二唑。首先，DMTMM 活化羧酸，然后与偕胺肟反应，转化为 O-酰化偕胺肟。不寻常的溶剂体系 THF-NMP 成功地促进了 O-酰化偕胺肟的脱水过程，并在一锅法中获得了 1,2,4-恶二唑。该方法提供了一种方便快捷的 1,2,4-恶二唑合成方法，产率高。