3-(2-naphthoyl)-4-hydroxy-3,4-dihydronaphthalen-1(2H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2-naphthoyl)-4-hydroxy-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: (3S,4R)-4-hydroxy-3-(naphthalene-2-carbonyl)-3,4-dihydro-2H-naphthalen-1-one
• 化学式: C₂₁H₁₆O₃
• 分子量: 316.356
• InChiKey: GGDKLMSZCWURDM-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-萘乙烯基酮 、 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52%的产率得到3-(2-naphthoyl)-4-hydroxy-3,4-dihydronaphthalen-1(2H)-one
  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.