diethyl 1-hydroxy-4-oxo-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate | 1202646-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 1-hydroxy-4-oxo-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate
• 英文别名: Diethyl 1-hydroxy-4-oxo-1,3-dihydronaphthalene-2,2-dicarboxylate
• CAS: 1202646-72-7
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: XOOLMFJHSAHEPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲撑丙二酸二乙酯 、 邻苯二甲醛 在 3-苄基羟乙基甲基噻唑氯化锂 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以57%的产率得到diethyl 1-hydroxy-4-oxo-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of 4-Hydroxytetralones via a Cascade Stetter−Aldol Reaction Catalyzed by N-Heterocyclic Carbenes

  摘要：

  A cascade Stetter-aldol reaction of phthalaldehyde and Michael acceptors catalyzed by N-heterocyclic carbenes was developed. The corresponding 3-substituted-4-hydroxytetralones were obtained in moderate to good yields with good trans-selectivities. On the contrary, the separated Stetter reaction followed by aldol reaction gave 3-substituted-4-hydroxytetralones with good cis-selectivity. Oxidation or dehydration of the resulted 4-hydroxytetralone gave the corresponding naphthalenediol or naphthol derivative, respectively, in good yield.

  DOI：

  10.1021/jo902376t

文献信息

• Diastereoselective Synthesis of 4-Hydroxytetralones via a Cascade Stetter−Aldol Reaction Catalyzed by <i>N</i>-Heterocyclic Carbenes
  作者：Fang-Gang Sun、Xue-Liang Huang、Song Ye

  DOI：10.1021/jo902376t

  日期：2010.1.1

  A cascade Stetter-aldol reaction of phthalaldehyde and Michael acceptors catalyzed by N-heterocyclic carbenes was developed. The corresponding 3-substituted-4-hydroxytetralones were obtained in moderate to good yields with good trans-selectivities. On the contrary, the separated Stetter reaction followed by aldol reaction gave 3-substituted-4-hydroxytetralones with good cis-selectivity. Oxidation or dehydration of the resulted 4-hydroxytetralone gave the corresponding naphthalenediol or naphthol derivative, respectively, in good yield.