7,7-dimethyl-4-(4'-bromophenyl)-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-(4'-bromophenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline
• 英文别名: 4-(4-bromophenyl)-7,7-dimethyl-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-dione；4-(4-bromophenyl)-7,7-dimethyl-3,4,6,8-tetrahydro-1H-quinoline-2,5-dione
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: CFWGBDXZJKAFDJ-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 、 3-氨基-5,5-二甲基-2-环己烯-1-酮 、 对溴苯甲醛 在 ionic liquid supported nanoporous silica 作用下， 以 neat (no solvent) 为溶剂， 反应 1.08h， 生成 7,7-dimethyl-4-(4'-bromophenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline
  参考文献：
  名称：

  Ionic liquid supported nanoporous silica (SBA-IL) as an efficient and heterogeneous catalyst in the domino synthesis of polyhydroquinoline derivatives

  摘要：

  开发了一种简单、有效且环境友好的聚氢喹啉衍生物合成方案，采用生物兼容的、异质的、可回收的中孔离子液体支持的纳米多孔二氧化硅作为纳米催化剂。聚氢喹啉衍生物通过醛、梅尔德鲁姆酸、二甲酮和醋酸铵的四组分反应以优良的产率获得。

  DOI：

  10.1007/s11164-015-2036-z

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
• 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。
• One-Pot Synthesis of 1,4-Dihydropyridine Derivatives Catalyzed by Silica-Coated Magnetic NiFe2O4 Nanoparticles-Supported H14[NaP5W30O110]
  作者：B. Maleki、A. V. Mofrad、R. Tayebee、A. Khojastehnezhad、H. Alinezhad、E. Rezaei Seresht

  DOI：10.1134/s1070363217120325

  日期：2017.12

  Silica-coated magnetic NiFe2O4 nanoparticles-supported H-14[NaP5W30O110] (NiFe2O4@SiO2-H-14[NaP5W30O110]) was successfully synthesized and shown to be a versatile and highly efficient heterogeneous catalyst for one-pot multicomponent synthesis of 1,4-dihydropyridine derivatives under solvent-free condition. The synthesized catalyst can be magnetically recovered and reused four times without significant loss in catalytic efficiency.
• Ionic liquid supported nanoporous silica (SBA-IL) as an efficient and heterogeneous catalyst in the domino synthesis of polyhydroquinoline derivatives
  作者：Ghodsi Mohammadi Ziarani、Leila Seyedakbari、Shima Asadi、Alireza Badiei、Marzieeh Yadavi

  DOI：10.1007/s11164-015-2036-z

  日期：2016.2

  A simple, efficient, and environmentally benign protocol for the synthesis of polyhydroquinoline derivatives was developed using a bio-compatible, heterogeneous, and recoverable mesoporous ionic liquid supported nanoporous silica as a nano-catalyst. The polyhydroquinoline derivatives were obtained by the four-component reaction of aldehyde, Meldrum’s acid, dimedone, and ammonium acetate in excellent yields .

  开发了一种简单、有效且环境友好的聚氢喹啉衍生物合成方案，采用生物兼容的、异质的、可回收的中孔离子液体支持的纳米多孔二氧化硅作为纳米催化剂。聚氢喹啉衍生物通过醛、梅尔德鲁姆酸、二甲酮和醋酸铵的四组分反应以优良的产率获得。