3,5-diphenyl-4-(phenylselenyl)isoxazole

• 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-(phenylselenyl)isoxazole
• 英文别名: 3,5-Diphenyl-4-phenylselanyl-1,2-oxazole
• 化学式: C₂₁H₁₅NOSe
• 分子量: 376.316
• InChiKey: OUCDITGLAWVEBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-diphenyl-4-(phenylselenyl)isoxazole 在 溴 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以85%的产率得到4-溴-3,5-二苯基异噁唑
  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
• 作为产物：
  描述：

  二苯基丙炔酮 在 吡啶 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3,5-diphenyl-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

• Synthesis of Isoxazoles via Electrophilic Cyclization
  作者：Jesse P. Waldo、Richard C. Larock

  DOI：10.1021/ol052027z

  日期：2005.11.1

  A variety of 3,5-disubstituted 4-halo(seleno)isoxazoles are readily prepared in good to excellent yields under mild reaction conditions by the reaction of 2-alkyn-1-one O-methyl oximes with ICI, I-2, Br-2, or PhSeBr.
• 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.