3,5-diphenyl-4-((3-(trifluoromethyl)phenyl)selenyl)isoxazole | 1422017-96-6

• 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: 3,5-diphenyl-4-((3-(trifluoromethyl)phenyl)selenyl)isoxazole
• 英文别名: 3,5-Diphenyl-4-[3-(trifluoromethyl)phenyl]selanyl-1,2-oxazole；3,5-diphenyl-4-[3-(trifluoromethyl)phenyl]selanyl-1,2-oxazole
• CAS: 1422017-96-6
• 化学式: C₂₂H₁₄F₃NOSe
• 分子量: 444.314
• InChiKey: JYBRYUYAQZORQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二苯基丙炔酮 在 吡啶 、 iron(III) chloride 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.41h， 生成 3,5-diphenyl-4-((3-(trifluoromethyl)phenyl)selenyl)isoxazole
  参考文献：
  名称：

  Iron(III) Chloride/Diorganyl Diselenides: A Tool for Intramolecular Cyclization of Alkynone O-Methyloximes

  摘要：

  This report describes the synthesis of 4-organoselenylisoxazoles via FeCl3/RSeSeR-mediated intramolecular cyclization of allcynone O-methyloximes. The optimized conditions allowed the cyclization to proceed at room temperature under ambient atmosphere, and the reaction requires a short time to be completed. The reaction conditions tolerated neutral, electron-donating and electron-withdrawing groups present in both substrates, alkynone O-methyloximes and diorganyl diselenides. Treatment of 4-organoselenylisoxazoles with n-butyllithium, followed by trapping with electrophiles, furnished the functionalized isoxazoles in good yields. The obtained products also proved to be suitable substrates for the preparation of 4-bromoisoxazoles via Br/Se exchange reaction.

  DOI：

  10.1021/jo302770g