(2aR,2a1S,5aR,10bS)-10b-hydroxy-4-methyl-2a1-propyl-2,2a,2a1,5,5a,10b-hexahydroaceanthrylene-1,6-dione | 1440538-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2aR,2a1S,5aR,10bS)-10b-hydroxy-4-methyl-2a1-propyl-2,2a,2a1,5,5a,10b-hexahydroaceanthrylene-1,6-dione
• CAS: 1440538-72-6
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: XYCDNUJFUGXQLU-PQTDTLSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-((4aR,9aS)-3-methyl-9,10-dioxo-9a-propyl-1,4,4a,9,9a,10-hexahydroanthracen-1-yl)acetaldehyde 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以67%的产率得到(2aR,2a1S,5aR,10bS)-10b-hydroxy-4-methyl-2a1-propyl-2,2a,2a1,5,5a,10b-hexahydroaceanthrylene-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