1-Quinolin-4-yl-butan-1-one | 132854-98-9

• 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-Quinolin-4-yl-butan-1-one
• 英文别名: 1-(4-Quinolinyl)-1-butanone；1-quinolin-4-ylbutan-1-one
• CAS: 132854-98-9
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: JBLUVCXCBMCQDW-UHFFFAOYSA-N

物化性质

• 沸点：
  338.2±15.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  喹啉 、 2-戊酮酸 在 NH₄S₂O₈ 、 硫酸 、 silver nitrate 作用下， 以 水 为溶剂， 反应 2.5h， 生成 1-(quinolin-2-yl)butan-1-one 、 1-Quinolin-4-yl-butan-1-one
  参考文献：
  名称：

  Homolytic acylation of protonated pyridines and pyrazines with .alpha.-keto acids: the problem of monoacylation

  摘要：

  The silver-catalyzed decarboxylation of alpha-keto acids by persulfate leads to acyl radicals, which can effect the selective homolytic acylation of pyridine and pyrazine derivatives. Compared with the previously developed source of acyl radicals by hydrogen abstraction from aldehydes, this procedure is more effective in monoacylation when multiple positions of high nucleophilic reactivity are available in the heterocyclic ring. Although the introduction of an acyl group strongly activates the heterocyclic ring toward further substitution, monoacylation can be achieved by taking advantage of the difference in basicity and lipophilicity between the starting base and the monoacylation products in a two-phase system.

  DOI：

  10.1021/jo00008a050

文献信息

• Radical C−H Acylation of Nitrogen Heterocycles Induced by an Aerobic Oxidation of Aldehydes
  作者：Subhasis Paul、Manotosh Bhakat、Joyram Guin

  DOI：10.1002/asia.201900857

  日期：2019.9.16

  ketones is described herein. The reaction involves cross-dehydrogenative coupling between aldehydes and heteroaromatic bases with molecular oxygen (O2 ). The key aspect of the method is the generation of reactive acyl radical via homolytic activation of aldehyde C-H bond using O2 as the sole oxidant. The reaction has a good substrate scope with respect to aldehydes and functionalized nitrogen heterocycles

  本文描述了用于合成不对称杂芳基酮的需氧自由基方法。该反应涉及醛和杂芳族碱与分子氧（O2）之间的交叉脱氢偶联。该方法的关键方面是使用O2作为唯一氧化剂，通过醛CH键的均质活化来生成反应性酰基基团。关于醛和官能化的氮杂环，该反应具有良好的底物范围。根据我们的机理研究，建议该反应采用自由基链途径。该方法的合成应用在天然生物碱（±）安格西汀的形式合成中得到了证明。
• Homolytic acylation of protonated pyridines and pyrazines with .alpha.-keto acids: the problem of monoacylation
  作者：Francesca Fontana、Francesco Minisci、Maria Claudia Nogueira Barbosa、Elena Vismara

  DOI：10.1021/jo00008a050

  日期：1991.4

  The silver-catalyzed decarboxylation of alpha-keto acids by persulfate leads to acyl radicals, which can effect the selective homolytic acylation of pyridine and pyrazine derivatives. Compared with the previously developed source of acyl radicals by hydrogen abstraction from aldehydes, this procedure is more effective in monoacylation when multiple positions of high nucleophilic reactivity are available in the heterocyclic ring. Although the introduction of an acyl group strongly activates the heterocyclic ring toward further substitution, monoacylation can be achieved by taking advantage of the difference in basicity and lipophilicity between the starting base and the monoacylation products in a two-phase system.