1,2,3,4,5,6,7,8-octahydrocyclodecanaphthalene-3,9,14-trione | 144767-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4,5,6,7,8-octahydrocyclodecanaphthalene-3,9,14-trione
• 英文别名: Tricyclo[8.8.0.03,8]octadeca-1(10),3,5,7-tetraene-2,9,13-trione
• CAS: 144767-48-6
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: POUPUULMINKJHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,4,5,6,7,8-octahydrocyclodecanaphthalene-3,9,14-trione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以65%的产率得到1,2,3,4-tetrahydrobenzanthracene-7,12-dione
  参考文献：
  名称：

  Studies in the benzannulation of a cycloalkynone: an approach to the synthesis of antibiotics containing the benz[a]anthracene core structure

  摘要：

  The chromium(0)-carbene complex benzannulation reaction was shown to be applicable to cyclodec-4-yn-1-one. Significant regioselectivity was realized in this reaction with ortho-substituted benzylchromium complexes. Reactions of a novel resultant fused cyclodecenone-naphthoquinone with several bases have been studied. Products apparently arising from either intramolecular Michael addition of a ketone enolate to the quinone or intramolecular aldol condensation of a quinone-stabilized anion with the ketone have been observed. The latter mode constitutes a route to the title substructure and, in principle, provides a route to reach certain angucycline antibiotics.

  DOI：

  10.1021/jo00052a014
• 作为产物：
  描述：

  1-Cyclodecyn-5-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 ammonium cerium(IV) nitrate 、 air 、 硝酸 作用下， 生成 1,2,3,4,5,6,7,8-octahydrocyclodecanaphthalene-3,9,14-trione
  参考文献：
  名称：

  Studies in the benzannulation of a cycloalkynone: an approach to the synthesis of antibiotics containing the benz[a]anthracene core structure

  摘要：

  The chromium(0)-carbene complex benzannulation reaction was shown to be applicable to cyclodec-4-yn-1-one. Significant regioselectivity was realized in this reaction with ortho-substituted benzylchromium complexes. Reactions of a novel resultant fused cyclodecenone-naphthoquinone with several bases have been studied. Products apparently arising from either intramolecular Michael addition of a ketone enolate to the quinone or intramolecular aldol condensation of a quinone-stabilized anion with the ketone have been observed. The latter mode constitutes a route to the title substructure and, in principle, provides a route to reach certain angucycline antibiotics.

  DOI：

  10.1021/jo00052a014

文献信息

• Studies in the benzannulation of a cycloalkynone: an approach to the synthesis of antibiotics containing the benz[a]anthracene core structure
  作者：Dana M. Gordon、Samuel J. Danishefsky、Gayle K. Schulte

  DOI：10.1021/jo00052a014

  日期：1992.12

  The chromium(0)-carbene complex benzannulation reaction was shown to be applicable to cyclodec-4-yn-1-one. Significant regioselectivity was realized in this reaction with ortho-substituted benzylchromium complexes. Reactions of a novel resultant fused cyclodecenone-naphthoquinone with several bases have been studied. Products apparently arising from either intramolecular Michael addition of a ketone enolate to the quinone or intramolecular aldol condensation of a quinone-stabilized anion with the ketone have been observed. The latter mode constitutes a route to the title substructure and, in principle, provides a route to reach certain angucycline antibiotics.