3-methyl-1-(4-phenylisoquinolin-1-yl)butan-1-one | 1597444-78-4

• 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: 3-methyl-1-(4-phenylisoquinolin-1-yl)butan-1-one
• 英文别名: 3-Methyl-1-(4-phenylisoquinolin-1-yl)butan-1-one
• CAS: 1597444-78-4
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: RUEXANPPYNXWNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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 、 异戊醛 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78%的产率得到3-methyl-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

• Transition metal-free Minisci reaction promoted by NCS, and TBHP: acylation of heteroarenes
  作者：Yogesh Siddaraju、Kandikere Ramaiah Prabhu

  DOI：10.1016/j.tet.2015.12.065

  日期：2016.2

  A method for acylation for heteroarenes under metal-free conditions has been described using NCS as an additive and TBHP as an oxidant. This method has been successfully employed in acylation of a variety of aldehyde with heteroarenes. The application of the method has been illustrated in synthesizing isoquinoline derived natural products. This strategy provides an efficient, mild and inexpensive method for acylation of heteroarenes. (C) 2015 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.