ethyl 2-amino-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 1334220-72-2

• 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: ethyl 2-amino-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: Ethyl 2-amino-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 1334220-72-2
• 化学式: C₂₀H₂₃BrN₂O₃
• 分子量: 419.318
• InChiKey: BZIXLPPZSFQKBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 对溴苯甲醛 、 氰乙酸乙酯 在 ammonium acetate 、 四丁基溴化铵 、 sodium carbonate 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到ethyl 2-amino-4-(4-bromophenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  钯（0）纳米颗粒：一种一锅合成聚氢喹啉的有效催化剂

  摘要：

  描述了一种温和，简洁，有效的方案，该方案通过使用Pd纳米粒子通过芳族醛，二甲酮，乙酰乙酸乙酯或氰基乙酸乙酯和乙酸铵的四组分反应合成聚氢喹啉。在一个锅中的芳基亚甲基双（3-羟基-2-环己烯-1-酮），乙酰乙酸乙酯，乙酸铵和Pd-纳米颗粒中也观察到相同的现象。本方法还允许我们从简单且容易获得的输入中合成高度官能化的标题化合物。

  DOI：

  10.1016/j.tetlet.2011.07.031

文献信息

• Catalyst-free, Knoevenagel-Michael Addition Reaction of Dimedone under Microwave Irradiation: An Efficient One-pot Synthesis of Polyhydroquinoline Derivatives
  作者：M. Saha、T. S. Luireingam、T. Merry、A. K. Pal

  DOI：10.1002/jhet.1541

  日期：2013.7

  concise and efficient protocol for the synthesis of polyhydroquinoline derivatives through coupling of four different components viz. aromatic aldehydes, dimedone, ethyl acetoacetate or ethyl cyanoacetate, and ammonium acetate. The same phenomenon can be observed using arylmethylene bis(3‐hydroxy‐2‐cyclohexene‐1‐ones), ethyl acetoacetate, and ammonium acetate in one pot under microwave irradiation. The key

  本研究报告了通过偶联四个不同组分合成聚氢喹啉衍生物的简洁有效的方案。芳族醛，二甲酮，乙酰乙酸乙酯或氰基乙酸乙酯和乙酸铵。在微波辐射下，在一个锅中使用芳基亚甲基双（3-羟基-2-环己烯-1-酮），乙酰乙酸乙酯和乙酸铵，可以观察到相同的现象。给定方案的主要优点包括反应时间短，产率高，后处理和纯化程序简单。本方法还允许我们从简单且容易获得的起始原料合成高度官能化的标题化合物。
• Chitosan Decorated Copper Nanoparticles as Efficient Catalyst for Synthesis of Novel Quinoline Derivatives
  作者：K. S. Alghamdi、N. S. I. Ahmed、D. Bakhotmah、M. Mokhtar

  DOI：10.1166/jnn.2020.16923

  日期：2020.2.1

  Chitosan decorated copper nanoparticles (CS/CuNPs) catalysts were synthesized via reduction methods utilizing green protocol. The CS/CuNPs hybrid catalysts were tested for the synthesis of quinoline derivatives utilizing one-pot multicomponent reaction (MCR) under ultrasonic irradiation. The optimized CS/CuNPs catalyst that provided good conversion reaction yield and high turnover frequency (TOF) was characterized using Fourier transform infrared (FTIR), thermogravimetric analyses (TGA), X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscope (TEM) and X-ray photoelectron spectroscopy (XPS) techniques. Generalization of the scope of the proposed catalytic process was studied using different aldehydes. Excellent products yield and high TOF in even shorter reaction time (similar to 5 min) was attained. Recyclability performance of the catalyst over five times re-use without detectable loss in product yield was recorded. The current method is green process utilizing environmentally benign catalyst and considered to be promising sustainable protocol for the synthesis of fine chemicals.