4,5-dimethoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate | 308803-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dimethoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate
• CAS: 308803-91-0
• 化学式: C₂₁H₁₉IO₅
• 分子量: 478.283
• InChiKey: QLFFLRDXDGZMQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate 在 bis-triphenylphosphine-palladium(II) chloride sodium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 1,10,12-trimethoxy-8-methyl-6H-dibenzo[c,h]chromen-6-one
  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：

  8-甲氧基-1,4-萘醌 在 4-二甲氨基吡啶 、 sodium dithionite 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 生成 4,5-dimethoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate
  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

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.