(5S)-5,8-dihydro-5-methyl-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S)-5,8-dihydro-5-methyl-1,4-naphthoquinone
• 英文别名: (5S)-5-methyl-5,8-dihydronaphthalene-1,4-dione
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: XSQJCCBRYZOAHR-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反-1,3-戊二烯 、 (+)-(S)-2-(p-tolylsulfinyl)cyclohexa-2,5-diene-1,4-dione 以 二氯甲烷 为溶剂， 反应 48.0h， 以71%的产率得到(5S)-5,8-dihydro-5-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  Influence of the Sulfinyl Group on the Chemoselectivity and π-Facial Selectivity of Diels−Alder Reactions of (S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone

  摘要：

  Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C-2-C-3 versus C-5-C-6 double bonds) is mainly related to the cyclic (on C-5-C-6) or acyclic (on C-2-C-3) structure of the diene. The high pi-facial selectivity observed could be controlled by choosing adequate experimental conditions.

  DOI：

  10.1021/jo951438y

文献信息

• Influence of the Sulfinyl Group on the Chemoselectivity and π-Facial Selectivity of Diels−Alder Reactions of <i>(S)</i>-2-(<i>p</i>-Tolylsulfinyl)-1,4-benzoquinone
  作者：M. Carmen Carreño、José L. García Ruano、Miguel A. Toledo、Antonio Urbano、Cynthia Z. Remor、Valter Stefani、Jean Fischer

  DOI：10.1021/jo951438y

  日期：1996.1.1

  Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyclohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C-2-C-3 versus C-5-C-6 double bonds) is mainly related to the cyclic (on C-5-C-6) or acyclic (on C-2-C-3) structure of the diene. The high pi-facial selectivity observed could be controlled by choosing adequate experimental conditions.