Tricyclo[12.4.0.04,9]octadeca-1(18),4,6,8,14,16-hexaen-2,12-diyn-11-ol | 1387598-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: Tricyclo[12.4.0.04,9]octadeca-1(18),4,6,8,14,16-hexaen-2,12-diyn-11-ol
• CAS: 1387598-22-2
• 化学式: C₁₈H₁₂O
• 分子量: 244.293
• InChiKey: GIONRBNNQHJGIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Tricyclo[12.4.0.04,9]octadeca-1(18),4,6,8,14,16-hexaen-2,12-diyn-11-ol 在 四溴化碳 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以17.2 mg的产率得到7,12-dibromo-5,6-dihydrotetraphen-6-ol
  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
• 作为产物：
  描述：

  2-(2-ethynylphenyl)acetaldehyde 在 吗啉 、 咪唑 、 chromium dichloride 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 copper(l) iodide 、 tetra-n-butylammoniumfluoride trihydrate 、 碘 、 potassium carbonate 、 戴斯-马丁氧化剂 、 二乙胺 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.17h， 生成 Tricyclo[12.4.0.04,9]octadeca-1(18),4,6,8,14,16-hexaen-2,12-diyn-11-ol
  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