1,10,12-trimethoxy-8-methyl-6H-dibenzo[c,h]chromen-6-one | 185103-21-3

• 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: 1,10,12-trimethoxy-8-methyl-6H-dibenzo[c,h]chromen-6-one
• 英文别名: 1,10,12-Trimethoxy-8-methylnaphtho[1,2-c]isochromen-6-one
• CAS: 185103-21-3
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: OHHGDFRTODNLQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,10,12-trimethoxy-8-methyl-6H-dibenzo[c,h]chromen-6-one 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以95%的产率得到2-(3-hydroxymethoxy-1,4-dioxo-1,4-dihydro-2-naphthyl)-3-methyl-5-methoxybenzoic acid
  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
• 作为产物：
  描述：

  2-iodo-3-methoxy-5-methylbenzoyl chloride 在 bis-triphenylphosphine-palladium(II) chloride 4-二甲氨基吡啶 、 sodium acetate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 丙酮 为溶剂， 反应 50.0h， 生成 1,10,12-trimethoxy-8-methyl-6H-dibenzo[c,h]chromen-6-one
  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

• Synthesis of C-aryl glycosides related to the chrysomycins
  作者：David J Hart、Gregory H Merriman、David G.J Young

  DOI：10.1016/0040-4020(96)00876-9

  日期：1996.11

  A synthesis of chrysomycin substructure 44 is described in which a Ramberg-Backlund reaction plays a key role. Electrochemical oxidation of 44 provided 45, and unsuccessful attempts to convert 45 to chrysomycin B (2) are presented.

  描述了金霉素亚结构44的合成，其中Ramberg-Backlund反应起关键作用。的电化学氧化44提供45，和不成功的尝试转换45至chrysomycin B（2）被呈现。
• Koyama, Hiroya; Kamikawa, Tadao, Journal of the Chemical Society. Perkin transactions I, 1998, # 2, p. 203 - 209
  作者：Koyama, Hiroya、Kamikawa, Tadao

  DOI：——

  日期：——
• 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.