5-(2-methoxyphenyl)-3-phenyl-4-(phenylselenyl)isoxazole | 1422018-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(2-methoxyphenyl)-3-phenyl-4-(phenylselenyl)isoxazole
• 英文别名: 5-(2-Methoxyphenyl)-3-phenyl-4-phenylselanyl-1,2-oxazole；5-(2-methoxyphenyl)-3-phenyl-4-phenylselanyl-1,2-oxazole
• CAS: 1422018-11-8
• 化学式: C₂₂H₁₇NO₂Se
• 分子量: 406.342
• InChiKey: OMEWSYXBBNGJEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.41h， 以57%的产率得到5-(2-methoxyphenyl)-3-phenyl-4-(phenylselenyl)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

文献信息

• Iron(III) Chloride/Diorganyl Diselenides: A Tool for Intramolecular Cyclization of Alkynone <i>O</i>-Methyloximes
  作者：Adriane Sperança、Benhur Godoi、Gilson Zeni

  DOI：10.1021/jo302770g

  日期：2013.2.15

  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.