(1R,9R,13R,17S)-11,17-dimethyl-16-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-2,4,6,11-tetraen-8-one | 1440538-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R,9R,13R,17S)-11,17-dimethyl-16-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-2,4,6,11-tetraen-8-one
• CAS: 1440538-73-7
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: QTPFNBGVIDMUAO-VFAJRCTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

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 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 、 二氯甲烷 为溶剂， 反应 2.0h， 以62%的产率得到(1R,9R,13R,17S)-11,17-dimethyl-16-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-2,4,6,11-tetraen-8-one
  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