6-hydroxy-5,6-dihydrotetraphene-7,12-dione | 1387598-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 6-hydroxy-5,6-dihydrotetraphene-7,12-dione
• 英文别名: 6-Hydroxy-5,6-dihydrobenzo[a]anthracene-7,12-dione；6-hydroxy-5,6-dihydrobenzo[a]anthracene-7,12-dione
• CAS: 1387598-21-1
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: OXISXLWJYLGPEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  7,12-dimethoxy-5,6-dihydrotetraphen-6-ol 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以75%的产率得到6-hydroxy-5,6-dihydrotetraphene-7,12-dione
  参考文献：
  名称：

  Synthetic Study of the Angular Tetracyclic Core Skeleton of Landmycine A via Masamune-Bergman Cyclization

  摘要：

  We describe the synthesis, via Masamune-Bergman cyclization, of an angucycline derivative involving a quinone in the B ring and a nonaromatic hydroxylated C ring. The naphthoquinone was synthesized via the copper-catalyzed Ullmann reaction of the dihalo aryl moiety, and the subsequent oxidation of a corresponding hydroquinone. The aryl dihalide was prepared by the dihalogenation of the 1,4-diradical generated during the Masamune-Bergman cyclization of the 1,2- dialkynylbenzene under neutral conditions. This methodology suggests a new route for the construction of natural products containing an anthraquinone skeleton.

  DOI：

  10.1055/s-0031-1290937

文献信息

• Synthetic Study of the Angular Tetracyclic Core Skeleton of Landmycine A via Masamune-Bergman Cyclization
  作者：Hiroshi Tanaka、Takashi Takahashi、Sho Yamaguchi、Ryo Yamada、Susumu Kawauchi

  DOI：10.1055/s-0031-1290937

  日期：2012.6

  We describe the synthesis, via Masamune-Bergman cyclization, of an angucycline derivative involving a quinone in the B ring and a nonaromatic hydroxylated C ring. The naphthoquinone was synthesized via the copper-catalyzed Ullmann reaction of the dihalo aryl moiety, and the subsequent oxidation of a corresponding hydroquinone. The aryl dihalide was prepared by the dihalogenation of the 1,4-diradical generated during the Masamune-Bergman cyclization of the 1,2- dialkynylbenzene under neutral conditions. This methodology suggests a new route for the construction of natural products containing an anthraquinone skeleton.