1-[3-(2-methoxyphenyl)-4-(3-p-tolyl-[1,2,4]oxadiazol-5-yl)isoxazol-5-yl]ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[3-(2-methoxyphenyl)-4-(3-p-tolyl-[1,2,4]oxadiazol-5-yl)isoxazol-5-yl]ethanol
• 英文别名: 1-[3-(2-Methoxyphenyl)-4-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]-1,2-oxazol-5-yl]ethanol；1-[3-(2-methoxyphenyl)-4-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]-1,2-oxazol-5-yl]ethanol
• 化学式: C₂₁H₁₉N₃O₄
• 分子量: 377.4
• InChiKey: BWCFGLDJCTYKJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对甲苯腈 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 生成 1-[3-(2-methoxyphenyl)-4-(3-p-tolyl-[1,2,4]oxadiazol-5-yl)isoxazol-5-yl]ethanol
  参考文献：
  名称：

  Solid-Phase Synthesis of 5-Isoxazol-4-yl-[1,2,4]oxadiazoles

  摘要：

  A library of isoxazole and 1,2,4-oxadiazole-containing diheterocyclic compounds has been prepared. Our strategy was explored in solution phase first as follows. PMB-protected 3-butyn-2-ol was deprotonated with nBuLi, acylated with methyl chloroformate, and then employed in a nitrile oxide 1,3-dipolar cycloaddition (benzaldehyde oxime in the presence of bleach) to afford the isoxazole-substituted carboxylic acid methyl ester. Ester saponification with aqueous NaOH followed by a two-step condensation with benzamidoxime gave the final isoxazole-oxadiazole diheterocyclic product in good yield. With some modifications, we next explored this chemistry on Wang resin, which led to 18 final products that were cleaved from polymer beads with 50% TFA in dichloromethane.

  DOI：

  10.1021/jo0352124