(2aR,5aR,10bS,10cS)-10b-hydroxy-4,10c-dimethyl-2,2a,5,5a-tetrahydroaceanthrylene-1,6-dione | 1440538-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2aR,5aR,10bS,10cS)-10b-hydroxy-4,10c-dimethyl-2,2a,5,5a-tetrahydroaceanthrylene-1,6-dione
• CAS: 1440538-71-5
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: DQOHEERFYJXTIE-RQXAQYCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  5-methyl-2,4-hexadienal 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 N,N-二乙基乙酰胺 、 (S)-2-(((2-((3,5-bis(trifluoromethyl)phenyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)pyrrolidin-1-ium 2,2,2-trifluoroacetate 、 sodium acetate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 25.0h， 生成 (2aR,5aR,10bS,10cS)-10b-hydroxy-4,10c-dimethyl-2,2a,5,5a-tetrahydroaceanthrylene-1,6-dione
  参考文献：
  名称：

  1,4-Naphthoquinones in H-Bond-Directed Trienamine-Mediated Strategies

  摘要：

  The synthesis of optically active, carboannulated dihydronaphthoquinone and naphthoquinone derivatives with up to four stereogenic centers is demonstrated by H-bond-directed, trienamine-mediated [4 + 2]-cycloadditions. The outcome of the reaction between 2,4-dienals and 1,4-naphthoquinones is controlled by the substituent in the 2-position of the 1,4-naphthoquinone. In the case of sterically demanding 2-substituted derivatives, dihydronaphthoquinones are obtained. However, when a hydrogen atom is present in the 2-position, a subsequent oxidation of the initially formed cycloadducts occurs yielding naphthoquinones.

  DOI：

  10.1021/ol401204a