1-butyl-2-(4-fluorophenyl)quinolin-4(1H)-one | 1395418-46-8

• 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: 1-butyl-2-(4-fluorophenyl)quinolin-4(1H)-one
• 英文别名: 1-Butyl-2-(4-fluorophenyl)quinolin-4-one；1-butyl-2-(4-fluorophenyl)quinolin-4-one
• CAS: 1395418-46-8
• 化学式: C₁₉H₁₈FNO
• 分子量: 295.356
• InChiKey: VZWZWDRVFRGVJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2,2-二溴乙烯基)-4-氟苯 在 manganese(IV) oxide 、 正丁基锂 、 potassium phosphate monohydrate 、 苄基三乙基氯化铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 1-butyl-2-(4-fluorophenyl)quinolin-4(1H)-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 One-Pot Tandem Synthesis of 4-Quinolone and 4H-Thiochromen-4-one Derivatives Through Sequential Nucleophilic Addition–Elimination–SNAr Reaction
  作者：Jinsong Peng、Chunxia Chen、Deqiang Wang、Peng Sun、Peiyun Jia、Yixia Yue

  DOI：10.1055/s-0036-1588466

  日期：2017.9

  transformed to 4-quinolone or 4H-thiochromen-4-one products through intramolecular SNAr reaction, respectively. 4-Quinolone and 4H-thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleo­philic addition of amines or sodium hydrogen sulfide to (Z)-β-chloro­vinyl ketones was followed by elimination

  摘要 4-喹诺酮和4 H-硫代色素-4-酮衍生物很容易以串联-一锅方式以良好至极好的产率合成。从（Z）-β-氯乙烯酮开始，分子间亲核加成胺或硫化氢钠到（Z）-β-氯乙烯酮中，然后消除氯阴离子，得到Z-烯胺或硫代烯醇中间体，可以将其转化通过分子内的S N Ar反应分别生成4-喹诺酮或4 H-硫代色素-4-酮。 4-喹诺酮和4 H-硫代色素-4-酮衍生物很容易以串联-一锅方式以良好至极好的产率合成。从（Z）-β-氯乙烯酮开始，分子间亲核加成胺或硫化氢钠到（Z）-β-氯乙烯酮中，然后消除氯阴离子，得到Z-烯胺或硫代烯醇中间体，可以将其转化通过分子内的S N Ar反应分别生成4-喹诺酮或4 H-硫代色素-4-酮。
• One-Pot Synthesis of Quinolin-4(1H)-one Derivatives by a Sequential Michael Addition–Elimination/Palladium-Catalyzed Buchwald–Hartwig Amination Reaction
  作者：Chunxia Chen、Jinsong Peng、Yinghua Wang、Hanyu Liang、Deqiang Wang

  DOI：10.1055/s-0034-1380496

  日期：——

  were transformed into quinolin-4(1H)-one products by a palladium-catalyzed intramolecular N-arylation in a tandem one-pot manner, with good to excellent yields. A convenient approach has been developed for the construction of quinolin-4(1H)-one frameworks, starting from (Z)-β-chlorovinyl aromatic ketones and amines. Intermolecular Michael addition of an amine to a (Z)-β-chlorovinyl ketone was followed

  摘要 从（Z）-β-氯乙烯基芳族酮和胺开始，已经开发了一种方便的方法来构建喹啉4（1 H）-one骨架。在（Z）-β-氯乙烯基酮的分子间迈克尔加成胺之后，消除氯离子，得到烯胺中间体，并完全保留了初始Z-构型。通过钯催化的分子内N-芳基化以串联-一锅方式将烯胺中间体转化为喹啉-4（1 H）-一产物，具有良好的优良的收率。 从（Z）-β-氯乙烯基芳族酮和胺开始，已经开发了一种方便的方法来构建喹啉4（1 H）-one骨架。在（Z）-β-氯乙烯基酮的分子间迈克尔加成胺之后，消除氯离子，得到烯胺中间体，并完全保留了初始Z-构型。通过钯催化的分子内N-芳基化以串联-一锅方式将烯胺中间体转化为喹啉-4（1 H）-一产物，具有良好的优良的收率。
• 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.