7,7-dimethyl-4-(2'-chlorophenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline

• 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: 7,7-dimethyl-4-(2'-chlorophenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline
• 英文别名: 4-(2'-chlorophenyl)-7,7-dimethyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline；4-(2-chlorophenyl)-7,7-dimethyl-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-dione；4-(2-chlorophenyl)-7,7-dimethyl-3,4,6,8-tetrahydro-1H-quinoline-2,5-dione
• 化学式: C₁₇H₁₈ClNO₂
• 分子量: 303.788
• InChiKey: XHEJWZHJCKBPQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 2-氯苯甲醛 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 反应 0.05h， 以79.4%的产率得到7,7-dimethyl-4-(2'-chlorophenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline
  参考文献：
  名称：

  微波辐照下无溶剂合成新型取代的2,5-二氧代-1,2,3,4,5,6,7,8-八氢喹啉

  摘要：

  描述了取代 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines 的一种方便的合成方法。将 Meldrum 的酸、二甲酮、醋酸铵和不同的芳香醛在微波辐射中加热 2-5 分钟，以 72-86% 的产率提供 4。这些化合物的结构已经通过 X 射线晶体学分析进行了彻底的研究。

  DOI：

  10.1081/scc-100105393

文献信息

• An efficient and green synthesis of 1,4-dihydropyridine derivatives through multi-component reaction in ionic liquid
  作者：Xue Sen Fan、Yan Zhen Li、Xin Ying Zhang、Gui Rong Qu、Jian Ji Wang、Xue Yuan Hu

  DOI：10.1002/hc.20221

  日期：——

  Through multi-component condensation of aldehydes, 1,3-dione, Meldrum's acid, and ammonium acetate in an ionic liquid ([bmim][BF4]), a series of 1,4-dihydropyridine derivatives were prepared in excellent yields in the absence of any additional catalysts. In addition, [bmim][BF4] can be recovered and reused effectively for at least six times without obvious decrease of its efficiency. Advantages of

  通过醛、1,3-二酮、Meldrum 酸和醋酸铵在离子液体 ([bmim][BF4]) 中的多组分缩合，在不存在的情况下以优异的收率制备了一系列 1,4-二氢吡啶衍生物任何额外的催化剂。此外，[bmim][BF4]可以有效回收利用至少6次，其效率没有明显下降。这种新协议的优点包括操作流程简单、环境友好、效率高。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:382–388, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20221
• A joint experimental and theoretical structural study of novel substituted 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines
  作者：Margarita Suárez、Estael Ochoa、Yamila Verdecia、Beatriz Pita、Lourdes Morán、Nazario Martín、Margarita Quinteiro、Carlos Seoane、JoséL Soto、Hector Novoa、Norbert Blaton、Oswald M Peters

  DOI：10.1016/s0040-4020(98)01078-3

  日期：1999.1

  A series of substituted 2,5-dioxo-1,2,3,4,5,5,7,8-octahydroquinolines have been synthesised from Meldrum's acid and dimedone in the presence of different aldehydes by following an approach similar to the one developed by Hantzch. The structure of these compounds has been thoroughly studied by X-ray crystallographic analysis and semiempirical (AM1) and ab initio (HF/3-21G) methods, and two favoured conformations are possible. A good agreement is found between the theoretical and experimental values. The most stable conformation (A) in the solid state is also that favoured in solution, according to the proton coupling constant determined from Karplus' and Altona's equations and H-1 NMR spectroscopic experiments. (C) 1998 Elsevier Science Ltd. All rights reserved.
• THE SYNTHESIS OF NOVEL SUBSTITUTED 2,5-DIOXO-1,2,3,4,5,6,7,8-OCTAHYDROQUINOLINES WITHOUT SOLVENT UNDER MICROWAVE IRRADIATION
  作者：Shujiang Tu、Qihua Wei、Hengjun Ma、Daqing Shi、Yuan Gao、Guiyou Cui

  DOI：10.1081/scc-100105393

  日期：2001.1.1

  A convenient synthetic method for substituted 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines is described. Heating Meldrum's acid, dimedone, ammonium acetate and different aromatic aldehydes without a solvent in a microwave irradiation for 2–5 minutes affords 4 in 72–86% yield. The structure of these compounds has been thoroughly studied by x-ray crystallographic analysis.

  描述了取代 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines 的一种方便的合成方法。将 Meldrum 的酸、二甲酮、醋酸铵和不同的芳香醛在微波辐射中加热 2-5 分钟，以 72-86% 的产率提供 4。这些化合物的结构已经通过 X 射线晶体学分析进行了彻底的研究。