4-hydroxy-5-methoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate | 281190-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-5-methoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate
• 英文别名: (4-Hydroxy-5-methoxynaphthalen-1-yl) 2-iodo-3-methoxy-5-methylbenzoate
• CAS: 281190-83-8
• 化学式: C₂₀H₁₇IO₅
• 分子量: 464.256
• InChiKey: RADJBHIUFSJGAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-methoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate 在 bis-triphenylphosphine-palladium(II) chloride sodium acetate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 丙酮 为溶剂， 反应 48.0h， 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
• 作为产物：
  描述：

  8-甲氧基-1,4-萘醌 在 4-二甲氨基吡啶 、 sodium dithionite 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.25h， 生成 4-hydroxy-5-methoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate
  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

• 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.