1-(quinolin-2-yl)butan-1-one | 51369-92-7

• 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-2-yl)butan-1-one
• 英文别名: Butyrylchinoline；1-quinolin-2-ylbutan-1-one
• CAS: 51369-92-7
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: YPUDAHAXAUXVBF-UHFFFAOYSA-N

物化性质

• 熔点：
  41-42 °C(Solv: ligroine (8032-32-4))
• 沸点：
  146-150 °C(Press: 3 Torr)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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

• 作为反应物：
  描述：

  1-(quinolin-2-yl)butan-1-one 、 2-氨基苯甲醛 在 氢氧化钾 作用下， 生成 3-ethyl-[2,2']biquinolyl
  参考文献：
  名称：

  The Synthesis of Certain Alkyl- and Phenyl-substituted 2,2'-Biquinolines¹

  摘要：

  DOI：

  10.1021/ja01116a013
• 作为产物：
  描述：

  喹啉 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(quinolin-2-yl)butan-1-one
  参考文献：
  名称：

  通过路易斯酸使能的光氧化还原催化对映选择性自由基加成酮

  摘要：

  光催化为羰基化学打开了一扇新窗。尽管羰基化合物有多种光化学反应，但可见光诱导的催化不对称转化仍然难以捉摸，并构成了巨大的挑战。因此，开发简单、高效、经济的催化体系是化学家的理想追求。在此，我们报告了通过路易斯酸启用的光氧化还原催化对酮的对映选择性自由基光加成，其中原位形成的手性N，N'-二氧化物/Sc(III)-酮络合物作为临时光催化剂触发单电子转移氧化用于产生亲核自由基物种的硅烷，包括伯、仲和叔烷基自由基，给出各种对映体富集基于氮杂杂环的叔醇，具有良好至优异的产率和对映选择性。电子顺磁共振（EPR）和高分辨率质谱（HRMS）测量结果为该反应中涉及的立体控制自由基加成过程提供了有利证据。

  DOI：

  10.1021/jacs.2c09691

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。
• 2-Quinolinecarboxaldehyde: an unusual partner in the Henry reaction and subsequent elimination
  作者：Ashley Nomland、Ivory D. Hills

  DOI：10.1016/j.tetlet.2008.07.044

  日期：2008.9

  2-Quinolinecarboxaldehyde participates in a standard Henry reaction when combined with a nitroalkane and catalytic amounts of base. However, water is not readily eliminated from the resulting beta-nitro alcohol intermediate to form the expected nitroalkene. Instead, the elimination of nitrous acid is observed furnishing an unexpected ketone product. (C) 2008 Elsevier Ltd. All rights reserved.
• A Transition Metal-Free Minisci Reaction: Acylation of Isoquinolines, Quinolines, and Quinoxaline
  作者：Yogesh Siddaraju、Manjunath Lamani、Kandikere Ramaiah Prabhu

  DOI：10.1021/jo500294z

  日期：2014.5.2

  Transition metal-free acylation of isoquinoline, quinoline, and quinoxaline derivatives has been developed employing a cross dehydrogenative coupling (CDC) reaction with aldehydes using substoichiometric amount of TBAB (tetrabutylammonium bromide, 30 mol %) and K2S2O8 as an oxidant. This intermolecular acylation of electron-deficient heteroarenes provides an easy access and a novel acylation method of heterocyclic compounds. The application of this CDC strategy for acylation strategy has been illustrated in synthesizing isoquinoline-derived natural products.
• Site‐Selective Pd‐Catalyzed C(sp ³ )−H Arylation of Heteroaromatic Ketones
  作者：Anton Kudashev、Olivier Baudoin

  DOI：10.1002/chem.202103467

  日期：2021.12.15

  AbstractA ligand‐controlled site‐selective C(sp3)−H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α‐ or β‐position of the ketone side‐chain. The switch from α‐ to β‐arylation was realized by addition of a pyridone ligand. The α‐arylation process showed broad scope and high site‐ and chemoselectivity, whereas the β‐arylation was more limited. Mechanistic investigations suggested that α‐arylation occurs through C−H activation/oxidative addition/reductive elimination whereas β‐arylation involves desaturation and aryl insertion.
• 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.