(2-Iodo-phenyl)-(1-methoxy-naphthalen-2-yl)-methanone | 1071046-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-Iodo-phenyl)-(1-methoxy-naphthalen-2-yl)-methanone
• 英文别名: (2-Iodophenyl)-(1-methoxynaphthalen-2-yl)methanone
• CAS: 1071046-85-9
• 化学式: C₁₈H₁₃IO₂
• 分子量: 388.205
• InChiKey: YYOJJKVPGGBFDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-Iodo-phenyl)-(1-methoxy-naphthalen-2-yl)-methanone 在 palladium diacetate sodium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 10.0h， 以85%的产率得到10-methoxy-11H-benzo[b]fluoren-11-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：

  naphthalen-1-yl-2-iodobenzoate 在 四氯化钛 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 26.0h， 生成 (2-Iodo-phenyl)-(1-methoxy-naphthalen-2-yl)-methanone
  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

• An intramolecular arylation route to the kinafluorenones
  作者：Ghassan Qabaja、Graham B Jones

  DOI：10.1016/s0040-4039(00)00848-0

  日期：2000.7

  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.