6-fluoro-3-(2-oxo-2-m-tolylethyl)-1H-isochromen-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-fluoro-3-(2-oxo-2-m-tolylethyl)-1H-isochromen-1-one
• 英文别名: 6-Fluoro-3-[2-(3-methylphenyl)-2-oxoethyl]isochromen-1-one；6-fluoro-3-[2-(3-methylphenyl)-2-oxoethyl]isochromen-1-one
• 化学式: C₁₈H₁₃FO₃
• 分子量: 296.298
• InChiKey: BFHHSGHGYHZQBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(1-hydroxybut-3-yn-yl)benzonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Jones reagent 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.17h， 生成 6-fluoro-3-(2-oxo-2-m-tolylethyl)-1H-isochromen-1-one
  参考文献：
  名称：

  Tunable Synthesis of 3-Acyl-2-naphthols and 3-Substituted Isocoumarins via Jones Reagent Promoted Cascade Reactions of 2-(4-Hydroxy-but-1-ynyl)benzaldehydes

  摘要：

  Novel and efficient synthesis of 3-acyl-2- 1) naphthols and 3-substituted isocoumarins via the tunable cascade reactions of 2-(4-hydroxy-but-1-ynyl)benzaldehydes have been developed. Treatment of 2-(4-hydroxy-but-1-ynyl)benzaldehydes with 0.7 equiv of Jones reagent in CH3CN and subsequent purification through column chromatography on silica gel pre-eluted with Et3N afforded 3-acyl-2-naphthols with high efficiency. When the same substrates were treated with 3 equiv of Jones reagents in acetone, on the other hand, 3-substituted isocoumarins could be obtained in good yields.

  DOI：

  10.1021/jo401502k

文献信息

• Tunable Synthesis of 3-Acyl-2-naphthols and 3-Substituted Isocoumarins via Jones Reagent Promoted Cascade Reactions of 2-(4-Hydroxy-but-1-ynyl)benzaldehydes
  作者：Yan He、Xinying Zhang、Nana Shen、Xuesen Fan

  DOI：10.1021/jo401502k

  日期：2013.10.18

  Novel and efficient synthesis of 3-acyl-2- 1) naphthols and 3-substituted isocoumarins via the tunable cascade reactions of 2-(4-hydroxy-but-1-ynyl)benzaldehydes have been developed. Treatment of 2-(4-hydroxy-but-1-ynyl)benzaldehydes with 0.7 equiv of Jones reagent in CH3CN and subsequent purification through column chromatography on silica gel pre-eluted with Et3N afforded 3-acyl-2-naphthols with high efficiency. When the same substrates were treated with 3 equiv of Jones reagents in acetone, on the other hand, 3-substituted isocoumarins could be obtained in good yields.