4-(4-diethylamino-1-methylbutylamino)quinoline-6-carboxylic acid methyl ester

• 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: 4-(4-diethylamino-1-methylbutylamino)quinoline-6-carboxylic acid methyl ester
• 英文别名: Methyl 4-[5-(diethylamino)pentan-2-ylamino]quinoline-6-carboxylate
• 化学式: C₂₀H₂₉N₃O₂
• 分子量: 343.469
• InChiKey: GOORBHGLOQGCQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氧代-1,4-二氢喹啉-6-羧酸甲酯 在 palladium diacetate potassium phosphate 、 三溴化磷 、 双(2-二苯基磷苯基)醚 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 4-(4-diethylamino-1-methylbutylamino)quinoline-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Assembly of 4-Aminoquinolines via Palladium Catalysis:  A Mild and Convenient Alternative to S_NAr Methodology

  摘要：

  4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)(2)/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.

  DOI：

  10.1021/jo062168u

文献信息

• Assembly of 4-Aminoquinolines via Palladium Catalysis:  A Mild and Convenient Alternative to S_NAr Methodology
  作者：Brandon J. Margolis、Kimberly A. Long、Dana L. T. Laird、J. Craig Ruble、Shon R. Pulley

  DOI：10.1021/jo062168u

  日期：2007.3.1

  4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)(2)/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.