(3-hydroxynaphthalen-2-yl)(thiophen-2-yl)methanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3-hydroxynaphthalen-2-yl)(thiophen-2-yl)methanone
• 英文别名: (3-hydroxy-2-naphthyl)(2-thienyl)methanone；(3-Hydroxynaphthalen-2-yl)-thiophen-2-ylmethanone
• 化学式: C₁₅H₁₀O₂S
• 分子量: 254.309
• InChiKey: RVSINDWRHWXWKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(thiophen-2-yl)but-3-yn-1-ol 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 (3-hydroxynaphthalen-2-yl)(thiophen-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

文献信息

• Synthesis of Aliphatic Hydroxyaryl Ketones or (Hetero)aryl Hydroxyaryl Ketones by Acylation of Organometallic Reagents
  作者：Alan Katritzky、Khanh Le、Prabhu Mohapatra

  DOI：10.1055/s-2007-990786

  日期：2007.10

  Diverse hydroxyarenecarboxylic acids afford stable N-(hydroxyaroyl)benzotriazoles that react with heteroaryl, alkyl, and aryl Grignard or lithium reagents to give the corresponding hydroxyaryl ketones in 51-94% yields.

  多样的羟基芳香羧酸可得到稳定的N-(羟基芳香酰)苯唑，这些苯唑与杂环芳烃、烷基和芳基格里尼亚反应或锂试剂反应，能够产生相应的羟基芳基酮，产率在51-94%之间。
• 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.