(5S)-2,5-dimethyl-5,8-dihydro-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)-2,5-dimethyl-5,8-dihydro-1,4-naphthoquinone
• 英文别名: (5S)-2,5-dimethyl-5,8-dihydronaphthalene-1,4-dione
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: NTDLASFJRKHWNT-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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_S)-5-methyl-2-(p-tolylsulfinyl)-1,4-benzoquinone 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到(5S)-2,5-dimethyl-5,8-dihydro-1,4-naphthoquinone
  参考文献：
  名称：

  Asymmetric Diels–Alder reactions of 5-substituted and 5,6-disubstituted (S)-2-(p-tolylsulfinyl)-1,4-benzoquinones with cyclopentadiene and trans-piperylene

  摘要：

  A systematic study of reactions between 5-substituted and 5,6-disubstituted (S)-2-p-tolylsulfinyl-p-benzoquinones and cyclopentadiene or trans-piperylene is reported. Complete regio and pi-facial selectivities are observed. The different behaviours of cyclic and acyclic dienes in the presence of ZnBr2 (cyclopentadiene showed reversed diastereoselection) and the role of BF3 . OEt2 are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00094-4

文献信息

• Asymmetric Diels–Alder reactions of 5-substituted and 5,6-disubstituted (S)-2-(p-tolylsulfinyl)-1,4-benzoquinones with cyclopentadiene and trans-piperylene
  作者：M.Carmen Carreño、José L Garcı́a Ruano、Celia Lafuente、Miguel A Toledo

  DOI：10.1016/s0957-4166(99)00094-4

  日期：1999.3

  A systematic study of reactions between 5-substituted and 5,6-disubstituted (S)-2-p-tolylsulfinyl-p-benzoquinones and cyclopentadiene or trans-piperylene is reported. Complete regio and pi-facial selectivities are observed. The different behaviours of cyclic and acyclic dienes in the presence of ZnBr2 (cyclopentadiene showed reversed diastereoselection) and the role of BF3 . OEt2 are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.