3-bromo-6-methoxy-1,2-dimethylquinolin-4(1H)-one | 1257665-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-bromo-6-methoxy-1,2-dimethylquinolin-4(1H)-one
• 英文别名: 3-Bromo-6-methoxy-1,2-dimethylquinolin-4-one
• CAS: 1257665-65-8
• 化学式: C₁₂H₁₂BrNO₂
• 分子量: 282.137
• InChiKey: TXSHODFUDHOGQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-6-methoxy-1,2-dimethylquinolin-4(1H)-one 、 3,5-二甲基苯硼酸 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 甲苯 为溶剂， 反应 4.5h， 以73%的产率得到3-(3,5-dimethylphenyl)-6-methoxy-1,2-dimethylquinolin-4(1H)-one
  参考文献：
  名称：

  Divergent Route to Access Structurally Diverse 4-Quinolones via Mono or Sequential Cross-Couplings

  摘要：

  A divergent route was developed to access 3-iodo- and 6-chloro-3-iodo-4(1H)-quinolones for further elaboration via mono and/or sequential Suzuki-Miyaura cross-coupling to generate novel and medicinally important 4(1H)-quinolones. Copper- and palladium-catalyzed cyanations were used to functionalize the 4-quinolone core further.

  DOI：

  10.1021/jo1014504
• 作为产物：
  描述：

  4-羟基-6-甲氧基-2-甲基喹啉 在 溴 、 caesium carbonate 、 potassium bromide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-bromo-6-methoxy-1,2-dimethylquinolin-4(1H)-one 、 3-Bromo-4,6-dimethoxy-2-methylquinoline
  参考文献：
  名称：

  Divergent Route to Access Structurally Diverse 4-Quinolones via Mono or Sequential Cross-Couplings

  摘要：

  A divergent route was developed to access 3-iodo- and 6-chloro-3-iodo-4(1H)-quinolones for further elaboration via mono and/or sequential Suzuki-Miyaura cross-coupling to generate novel and medicinally important 4(1H)-quinolones. Copper- and palladium-catalyzed cyanations were used to functionalize the 4-quinolone core further.

  DOI：

  10.1021/jo1014504

文献信息

• Divergent Route to Access Structurally Diverse 4-Quinolones via Mono or Sequential Cross-Couplings
  作者：R. Matthew Cross、Roman Manetsch

  DOI：10.1021/jo1014504

  日期：2010.12.17

  A divergent route was developed to access 3-iodo- and 6-chloro-3-iodo-4(1H)-quinolones for further elaboration via mono and/or sequential Suzuki-Miyaura cross-coupling to generate novel and medicinally important 4(1H)-quinolones. Copper- and palladium-catalyzed cyanations were used to functionalize the 4-quinolone core further.