4-fluoro-3-methyl-5-phenylisoxazole | 1616956-25-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-fluoro-3-methyl-5-phenylisoxazole
• 英文别名: 4-Fluoro-3-methyl-5-phenyl-1,2-oxazole；4-fluoro-3-methyl-5-phenyl-1,2-oxazole
• CAS: 1616956-25-2
• 化学式: C₁₀H₈FNO
• 分子量: 177.178
• InChiKey: LWAGZFITLHCRFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-4-phenylbut-3-yn-2-one O-methyl oxime 在 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 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 4.5h， 以92%的产率得到4-fluoro-3-methyl-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

• Synthesis of 3,4,5-Trisubstituted Isoxazoles through Gold-Catalyzed Cascade Cyclization-Oxidative Alkynylation and Cyclization-Fluorination of 2-Alkynone O-Methyloximes
  作者：Doo-Hee Song、Jae-Sang Ryu

  DOI：10.5012/bkcs.2014.35.9.2635

  日期：2014.9.20

  Gold-catalyzed tandem cyclization-oxidative alkynylation and cyclization-fluorination reactions of 2-alkynone O-methyloximes are described. The reactions proceed smoothly at room temperature in the presence of 10 mol % of $(PPh_3)AuNTf_2$, 2.5 equivalents of selectfluor, and 2 equivalents of $K_3PO_4$. 2-Alkynone O-methyloximes undergo intramolecular oxyauration/cyclization and ensuing oxidative cross-coupling and fluorination process to afford the corresponding 3,4,5-trisubstituted isoxazoles in a cascade manner.

  报道了2-炔酮O-甲基肟的金银催化的串联环化-氧化炔基化和环化-氟化反应。在室温下，反应在10 mol%的$(PPh_3)AuNTf_2$、2.5当量的selectfluor和2当量的$K_3PO_4$存在下顺利进行。2-炔酮O-甲基肟经历了分子内的氧杂环化/环化以及随后的氧化交叉耦合和氟化过程，以串联方式提供了相应的3,4,5-三取代的异恶唑。
• 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.