5-(4-Fluorophenyl)-2-methyl-3-phenylmethoxypyran-4-one | 152804-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-(4-Fluorophenyl)-2-methyl-3-phenylmethoxypyran-4-one
• CAS: 152804-90-5
• 化学式: C₁₉H₁₅FO₃
• 分子量: 310.325
• InChiKey: LBESRHJIXCZKKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-Fluorophenyl)-2-methyl-3-phenylmethoxypyran-4-one 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以79%的产率得到5-(4-Fluorophenyl)-3-hydroxy-2-methylpyran-4-one
  参考文献：
  名称：

  Synthesis of 5-Aryl-3-hydroxy-4H-pyran-4-ones

  摘要：

  The palladium-catalyzed coupling reaction of 3-benzyl-oxy-5-bromo-2-methyl-4H-pyran-4-one (2b) with phenylboronic acid afforded efficiently 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one (3b-1), and the benzyloxy group of the resultant product was cleaved by hydrolysis with conc. hydrochloric acid in acetic acid to give 5-phenyl-3-hydroxy-2-methyl-4H-pyran-4-one (4b-1) in high yield. This method was applicable as a general method for synthesizing 5-aryl-3-hydroxy-4H-pyran-4-ones (4) from the 5-bromo-4H-pyran-4-ones(1).

  DOI：

  10.3987/com-93-6364
• 作为产物：
  描述：

  5-溴-3-羟基-2-甲基吡喃-4-酮 在 四(三苯基膦)钯 、 双氧水 、 sodium hydride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 5-(4-Fluorophenyl)-2-methyl-3-phenylmethoxypyran-4-one
  参考文献：
  名称：

  Synthesis of 5-Aryl-3-hydroxy-4H-pyran-4-ones

  摘要：

  The palladium-catalyzed coupling reaction of 3-benzyl-oxy-5-bromo-2-methyl-4H-pyran-4-one (2b) with phenylboronic acid afforded efficiently 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one (3b-1), and the benzyloxy group of the resultant product was cleaved by hydrolysis with conc. hydrochloric acid in acetic acid to give 5-phenyl-3-hydroxy-2-methyl-4H-pyran-4-one (4b-1) in high yield. This method was applicable as a general method for synthesizing 5-aryl-3-hydroxy-4H-pyran-4-ones (4) from the 5-bromo-4H-pyran-4-ones(1).

  DOI：

  10.3987/com-93-6364

文献信息

• Synthesis of 5-Aryl-3-hydroxy-4H-pyran-4-ones
  作者：Hisashi Takao、Yoshinori Endo、Tokunaru Horie

  DOI：10.3987/com-93-6364

  日期：——

  The palladium-catalyzed coupling reaction of 3-benzyl-oxy-5-bromo-2-methyl-4H-pyran-4-one (2b) with phenylboronic acid afforded efficiently 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one (3b-1), and the benzyloxy group of the resultant product was cleaved by hydrolysis with conc. hydrochloric acid in acetic acid to give 5-phenyl-3-hydroxy-2-methyl-4H-pyran-4-one (4b-1) in high yield. This method was applicable as a general method for synthesizing 5-aryl-3-hydroxy-4H-pyran-4-ones (4) from the 5-bromo-4H-pyran-4-ones(1).