3-bromo-1,2-dimethyl-quinolin-4(1H)-one | 1257665-61-4

• 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-1,2-dimethyl-quinolin-4(1H)-one
• 英文别名: 3-bromo-1,2-dimethylquinolin-4(1H)-one；3-Bromo-1,2-dimethylquinolin-4-one
• CAS: 1257665-61-4
• 化学式: C₁₁H₁₀BrNO
• 分子量: 252.11
• InChiKey: XOSKAEZNELMQEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-1,2-dimethyl-quinolin-4(1H)-one 、 2-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 1.0h， 以83%的产率得到1,2-dimethyl-3-o-tolylquinolin-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：

  苯胺 在 溴 、 caesium carbonate 、 溶剂黄146 、 potassium bromide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 19.0h， 生成 3-bromo-4-methoxy-2-methyl-quinoline 、 3-bromo-1,2-dimethyl-quinolin-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

文献信息

• Endochin Optimization: Structure−Activity and Structure−Property Relationship Studies of 3-Substituted 2-Methyl-4(1<i>H</i>)-quinolones with Antimalarial Activity
  作者：R. Matthew Cross、Andrii Monastyrskyi、Tina S. Mutka、Jeremy N. Burrows、Dennis E. Kyle、Roman Manetsch

  DOI：10.1021/jm1007903

  日期：2010.10.14

  Since the 1940s endochin and analogues thereof were known to be causal prophylactic and potent erythrocytic stage agents in avian models. Preliminary screening in a current in vitro assay identified several 4(1H)-quinolones with nanomolar EC(50) against erythrocytic stages of mullidrug resistant W2 and TM90-C2B isolates of Plasmodium folciparum. Follow-up structure activity relationship (SAR) studies on 4(1H)-quinolone analogues identified several key features for biological activity. Nevertheless, structure property relationship (SPR) studies conducted in parallel revealed that 4(1H)-quinolone analogues are limited by poor solubilities and rapid microsomal degradations. To improve the overall efficacy, multiple 4(1H)-quinolone series with varying substituents on the benzenoid quinolone ring and/or the 3-position were synthesized and tested for in vitro antimalarial activity. Several structurally diverse 6-chloro-2-methyl-7-methoxy-4(1H)-quinolones with EC(50) in the low nanomolar range against the clinically relevant isolates W2 and TM90-C2B were identified with improved physicochemical properties while maintaining little to no cross-resistance with atovaquone.
• 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.