1-butyl-2-(4-methoxy-phenyl)-1H-quinolin-4-one | 1395418-44-6

• 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: 1-butyl-2-(4-methoxy-phenyl)-1H-quinolin-4-one
• 英文别名: 1-Butyl-2-(4-methoxyphenyl)quinolin-4-one
• CAS: 1395418-44-6
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: FOUJOAJDMQKEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• 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

• 作为产物：
  描述：

  4-乙炔基苯甲醚 在 manganese(IV) oxide 、 正丁基锂 、 potassium phosphate monohydrate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 13.5h， 生成 1-butyl-2-(4-methoxy-phenyl)-1H-quinolin-4-one
  参考文献：
  名称：

  Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation

  摘要：

  N-Alkyl-substituted 4-quinolones are present as the key structural motif in many marketed drugs. An efficient one-step tandem amination approach was developed to afford N-alkyl-substituted 4-quinolones in high yields from easily accessible o-chloroaryl acetylenic ketones and functionalized alkyl amines. The approach complements and extends our previous work. Compared with other reported methods, the current method provides a very simple and convenient route.

  DOI：

  10.1055/s-0031-1290775

文献信息

• Transition-metal-free solid phase synthesis of 1,2-disubstituted 4-quinolones via the regiospecific synthesis of enaminones
  作者：Ajjampura C. Vinayaka、Toreshettahally R. Swaroop、Prasanna Kumara Chikkade、Kanchugarakoppal S. Rangappa、Maralinganadoddi P. Sadashiva

  DOI：10.1039/c5ra21421a

  日期：——

  Herein, the transition-metal-free economical solid phase synthesis of 1,2-disubstituted 4-quinolones has been developed via the novel regiospecific synthesis of enaminones. Notably, a wide range of enaminones were synthesized via a silica-supported solid-phase reaction in good to excellent yields. The transformation of enaminones to 1,2-disubstituted 4-quinolones and N-methyl-2-aryl-4-quinolone alkaloid

  在此，通过新型的烯胺酮的区域特异性合成，已经开发了无过渡金属的1，2-二取代的4-喹诺酮的经济固相合成。值得注意的是，通过二氧化硅负载的固相反应以良好至优异的产率合成了宽范围的烯胺酮。通过氧化铝负载的固相反应以高收率实现烯胺酮向1，2-二取代的4-喹诺酮和N-甲基-2-芳基-4-喹诺酮生物碱的转化。此外，所有合成的化合物都可以通过简单的后处理程序直接从反应混合物中以纯净的形式分离出来。
• Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation
  作者：Bin Xu、Jun Shao、Xiaomei Huang、Xiaohu Hong、Bingxin Liu

  DOI：10.1055/s-0031-1290775

  日期：2012.6

  N-Alkyl-substituted 4-quinolones are present as the key structural motif in many marketed drugs. An efficient one-step tandem amination approach was developed to afford N-alkyl-substituted 4-quinolones in high yields from easily accessible o-chloroaryl acetylenic ketones and functionalized alkyl amines. The approach complements and extends our previous work. Compared with other reported methods, the current method provides a very simple and convenient route.