(2-碘-3-甲氧基-5-甲基苯基)(1,4,8-三甲氧基-2-萘基)甲酮 | 289911-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-碘-3-甲氧基-5-甲基苯基)(1,4,8-三甲氧基-2-萘基)甲酮
• 英文名称: (2-iodo-3-methoxy-5-methylphenyl)(1,4,8-trimethoxy-2-naphthyl)methanone
• 英文别名: (2-Iodo-3-methoxy-5-methylphenyl)-(1,4,8-trimethoxynaphthalen-2-yl)methanone
• CAS: 289911-22-4
• 化学式: C₂₂H₂₁IO₅
• 分子量: 492.31
• InChiKey: OATZXPIRNWCEBA-UHFFFAOYSA-N

物化性质

• 熔点：
  160-162 °C
• 沸点：
  622.0±55.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (2-碘-3-甲氧基-5-甲基苯基)(1,4,8-三甲氧基-2-萘基)甲酮 在 bis-triphenylphosphine-palladium(II) chloride sodium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.02h， 以53%的产率得到tri-O-methylkinafluorenone
  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-溴-1,4,8-三甲氧基萘 在 叔丁基锂 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (2-碘-3-甲氧基-5-甲基苯基)(1,4,8-三甲氧基-2-萘基)甲酮
  参考文献：
  名称：

  An intramolecular arylation route to the kinafluorenones

  摘要：

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of kinafluorenone 2, providing an effective alternative to Friedel-Crafts-based approaches. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00848-0