7,7-dimethyl-4-phenyl-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-phenyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline
• 英文别名: 4-phenyl-7,7-dimethyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline；2-hydroxy-7,7-dimethyl-4-phenyl-4,6,7,8-tetrahydroquinolin-5(3H)-one；7,7-dimethyl-4-phenyl-3,4,6,8-tetrahydro-1H-quinoline-2,5-dione
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: XZQDWVORGQYWMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 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：

  3-(2,2-dimethylhydrazino)-5,5-dimethylcyclohex-2-en-1-one 在 溶剂黄146 、 锌 作用下， 生成 7,7-dimethyl-4-phenyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinoline
  参考文献：
  名称：

  Asymmetric Michael addition/lactamization via samp-/ramp-hydrazonesenantioselective synthesis of substituted tetrahydro-2,5(1H,3H)-quinolinediones

  摘要：

  DOI：

  10.1016/s0040-4039(00)96386-x

文献信息

• N-Heterocyclic Carbene Catalyzed Reactions of α-Bromo-α,β-unsaturated Aldehydes/α,β-Dibromoaldehydes with 1,3-Dinucleophilic Reagents
  作者：Changsheng Yao、Donglin Wang、Jun Lu、Tuanjie Li、Weihui Jiao、Chenxia Yu

  DOI：10.1002/chem.201103358

  日期：2012.2.13

  Carbenes ring true: N‐Heterocyclic carbene (NHC) catalyzed reactions of α‐bromo‐α,β‐unsaturated aldehydes/α,β‐dibromoaldehydes with 1,3‐dinucleophilic reagents, such as 1,3‐dicarbonyl compounds, β‐enamino ketones, and β‐enamino esters through umpolung processes gave functionalized 3,4‐dihydropyranones and 3,4‐dihydropyridinones (see scheme). The availability of the starting materials, lack of external

  Carbenes正确：N-杂环卡宾（NHC）催化α-溴代α，β-不饱和醛/α，β-二溴代醛与1,3-二亲核试剂（例如1,3-二羰基化合物，β-烯氨基）的反应通过umpolung工艺获得的酮和β-烯胺酯可得到功能化的3,4-二氢吡喃酮和3,4-二氢吡啶酮（参见方案）。原材料的可用性，缺乏外部氧化剂以及产品的实用性使该策略具有吸引力。
• 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
• 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。
• 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.