1-(4-phenylisoquinolin-1-yl)butan-1-one | 1597444-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(4-phenylisoquinolin-1-yl)butan-1-one
• 英文别名: 1-(4-Phenylisoquinolin-1-yl)butan-1-one
• CAS: 1597444-79-5
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: FGBUMEYQPXIAIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  4-phenylisoquinoline 、 正丁醛 在 dipotassium peroxodisulfate 、 四丁基溴化铵 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以60%的产率得到1-(4-phenylisoquinolin-1-yl)butan-1-one
  参考文献：
  名称：

  A Transition Metal-Free Minisci Reaction: Acylation of Isoquinolines, Quinolines, and Quinoxaline

  摘要：

  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.

  DOI：

  10.1021/jo500294z

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。
• 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.