4-fluoro-3-(3-methoxyphenyl)-5-phenylisoxazole | 1616956-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-fluoro-3-(3-methoxyphenyl)-5-phenylisoxazole
• 英文别名: 4-Fluoro-3-(3-methoxyphenyl)-5-phenyl-1,2-oxazole；4-fluoro-3-(3-methoxyphenyl)-5-phenyl-1,2-oxazole
• CAS: 1616956-32-1
• 化学式: C₁₆H₁₂FNO₂
• 分子量: 269.275
• InChiKey: BKOZRZRLOMZNBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(3-methoxyphenyl)-3-phenyl-2-propyn-1ol 在 吡啶 、 manganese(IV) oxide 、 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 silver toluene-p-sulfonate 、 碳酸氢钠 、 sodium sulfate 、 Selectfluor 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 44.5h， 生成 4-fluoro-3-(3-methoxyphenyl)-5-phenylisoxazole 、 3-(3-methoxyphenyl)-5-phenylisoxazole
  参考文献：
  名称：

  Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone O-Methyl Oximes

  摘要：

  A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl mimes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.

  DOI：

  10.1021/jo5008702

文献信息

• Direct Synthesis of 4-Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2-Alkynone <i>O</i>-Methyl Oximes
  作者：Yunkyung Jeong、Bom-I Kim、Jae Kyun Lee、Jae-Sang Ryu

  DOI：10.1021/jo5008702

  日期：2014.7.18

  A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl mimes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.