1,10-dimethoxy-8-methyl-11,12-dihydro-6H-dibenzo[c,h]chromene-6,11,12-trione | 281190-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 1,10-dimethoxy-8-methyl-11,12-dihydro-6H-dibenzo[c,h]chromene-6,11,12-trione
• 英文别名: 1,10-Dimethoxy-8-methylnaphtho[1,2-c]isochromene-6,11,12-trione
• CAS: 281190-85-0
• 化学式: C₂₀H₁₄O₆
• 分子量: 350.328
• InChiKey: ZFVQJCPYZSPLKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,10-dimethoxy-8-methyl-11,12-dihydro-6H-dibenzo[c,h]chromene-6,11,12-trione 在 氢氧化钾 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Antibiotic WS-5995 C
  参考文献：
  名称：

  Regioselective lactonization of naphthoquinones: synthesis and antitumoral activity of the WS-5995 antibiotics

  摘要：

  An acid promoted quinolactonization of naphthoquinones has been developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C and functional analogs is demonstrated. Preliminary antitumoral activity of the analogs is presented together with electrochemical analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00329-4
• 作为产物：
  描述：

  2-(3-hydroxymethoxy-1,4-dioxo-1,4-dihydro-2-naphthyl)-3-methyl-5-methoxybenzoic acid 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到1,10-dimethoxy-8-methyl-11,12-dihydro-6H-dibenzo[c,h]chromene-6,11,12-trione
  参考文献：
  名称：

  Annulation Strategies for Benzo[b]fluorene Synthesis:  Efficient Routes to the Kinafluorenone and WS-5995 Antibiotics

  摘要：

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative td Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.

  DOI：

  10.1021/jo0056186

文献信息

• Annulation Strategies for Benzo[<i>b</i>]fluorene Synthesis:  Efficient Routes to the Kinafluorenone and WS-5995 Antibiotics
  作者：Ghassan Qabaja、Graham B. Jones

  DOI：10.1021/jo0056186

  日期：2000.10.1

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative td Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.
• Regioselective lactonization of naphthoquinones: synthesis and antitumoral activity of the WS-5995 antibiotics
  作者：Ghassan Qabaja、Elisabeth M. Perchellet、Jean-Pierre Perchellet、Graham B Jones

  DOI：10.1016/s0040-4039(00)00329-4

  日期：2000.4

  An acid promoted quinolactonization of naphthoquinones has been developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C and functional analogs is demonstrated. Preliminary antitumoral activity of the analogs is presented together with electrochemical analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.