(2-bromo-4-fluorophenyl)(3-hydroxy-6-methylnaphthalen-2-yl)methanone

• 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: (2-bromo-4-fluorophenyl)(3-hydroxy-6-methylnaphthalen-2-yl)methanone
• 英文别名: (2-Bromo-4-fluorophenyl)-(3-hydroxy-6-methylnaphthalen-2-yl)methanone；(2-bromo-4-fluorophenyl)-(3-hydroxy-6-methylnaphthalen-2-yl)methanone
• 化学式: C₁₈H₁₂BrFO₂
• 分子量: 359.194
• InChiKey: BKMOMQJPOOTIQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-(2-bromo-4-fluorophenyl)-4-hydroxybut-1-ynyl)-4-methylbenzaldehyde 在 Jones reagent 、 三乙胺 作用下， 以 乙腈 、 乙醚 、 乙酸乙酯 为溶剂， 反应 0.17h， 以240 mg的产率得到(2-bromo-4-fluorophenyl)(3-hydroxy-6-methylnaphthalen-2-yl)methanone
  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