4,6,7,8-tetrahydro-7,7-dimethyl-4-(4-nitrophenyl)-2-phenyl-5(1H)-quinolinone | 916503-02-1

• 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: 4,6,7,8-tetrahydro-7,7-dimethyl-4-(4-nitrophenyl)-2-phenyl-5(1H)-quinolinone
• 英文别名: 7,7-dimethyl-5-oxo-2-phenyl-4-(4-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline；7,7-dimethyl-2-phenyl-4-(4-nitrophenyl)-1,4,5,6,7,8-hexahydroquinoline-5-one；7,7-dimethyl-4-(4-nitrophenyl)-5-oxo-2-phenyl-1,4,5,6,7,8-hexahydroquinoline；7,7-dimethyl-4-(4-nitrophenyl)-2-phenyl-4,6,7,8-tetrahydroquinolin-5(1H)-one；7,7-dimethyl-4-(4-nitrophenyl)-2-phenyl-1,4,6,8-tetrahydroquinolin-5-one
• CAS: 916503-02-1
• 化学式: C₂₃H₂₂N₂O₃
• 分子量: 374.439
• InChiKey: GORGSJPQRKOBBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6,7,8-tetrahydro-7,7-dimethyl-4-(4-nitrophenyl)-2-phenyl-5(1H)-quinolinone 以 乙腈 为溶剂， 以22%的产率得到7,7-Dimethyl-4-(4-nitrophenyl)-2-phenyl-6,8-dihydroquinolin-5-one
  参考文献：
  名称：

  2, 4-二芳基-5-氧代六氢喹啉的光氧化芳构化和光重排

  摘要：

  合成了各种2,4-双芳基取代的5-氧代六氢喹啉，并研究了2-和4-取代对这些化合物的光化学行为的电子效应。这些化合物的紫外光照射导致发生两种类型的光反应：氧化 正常的光氧化和光重排反应。在这两个反应中，均观察到杂环1,4-二氢吡啶环芳构化为吡啶环。光化学结果表明自由基中间体的参与，负责芳环迁移和光重排反应的发生。实验工作和DFT计算研究的结果支持了所涉及的自由基中间体的捕获自由基稳定化的部分协同效应。两种5-氧代六氢喹啉化合物的X射线晶体结构分析表明i ) 。C 4 -芳基环占据杂环二氢吡啶环的扭船构象的假轴位置，并且， ii )。由于空间邻位排斥，C 2 -芳基环具有关于杂环的连接的C C 双键的非平面取向。这些观察结果与 DFT 计算研究和 X 射线晶体结构分析的数据非常一致。

  DOI：

  10.1016/j.jphotochem.2023.115414
• 作为产物：
  描述：

  4-硝基查耳酮 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以36%的产率得到4,6,7,8-tetrahydro-7,7-dimethyl-4-(4-nitrophenyl)-2-phenyl-5(1H)-quinolinone
  参考文献：
  名称：

  对位取代的苯甲醛作为对苯二酚的氧化芳构化的权宜试剂

  摘要：

  四氢-5（1 H）-喹啉酮与对位取代的苯甲醛在碱存在下的Cannizzaro型反应形成相应的喹啉和芳基甲醇而不是亚芳基衍生物，因为四氢喹啉被氧化并由于从四氢喹啉到芳醛的前所未有的氢化物转移。在具有+ M效应的取代基参与底物分子的过程中，反应进行得最好。

  DOI：

  10.1002/jhet.1117

文献信息

• Efficient synthesis of 2,4-diaryl hexahydroquinoline-5-one derivatives in the presence of triethylamine
  作者：Zahed Karimi-Jaberi、Maryam Azadi

  DOI：10.1007/s11164-014-1773-8

  日期：2015.9

  A convenient and efficient protocol for the synthesis of 2,4-diaryl hexahydroquinoline-5-one derivatives has been accomplished by a three-component reaction of 1,3-diaryl-2-propen-1-ones, dimedone and ammonium acetate catalyzed by triethylamine under solvent-free conditions. The simple experimental procedure, use of an inexpensive catalyst, short reaction times, and excellent yields make this procedure

  一种方便有效的合成2,4-二芳基六氢喹啉-5-酮衍生物的方案是通过1,3-二芳基-2-丙烯-1-酮，二甲酮和乙酸铵的三组分反应催化的。三乙胺在无溶剂条件下使用。简单的实验程序，使用廉价的催化剂，短的反应时间和优异的收率使得该程序容易，实用和可持续。
• Silica-supported perchloric acid (HClO4–SiO2): a mild, reusable and highly efficient heterogeneous catalyst for multicomponent synthesis of 1,4-dihydropyridines via unsymmetrical Hantzsch reaction
  作者：Syed Sheik Mansoor、Krishnamoorthy Aswin、Kuppan Logaiya、Prasanna Nitiya Sudhan、Saleem Malik

  DOI：10.1007/s11164-012-0968-0

  日期：2014.1

  Facile synthesis of some 1,4-dihydropyridine derivatives via Hantzsch reaction of 5,5-dimethyl-1,3-cyclohexanedione (dimedone), 1,3-diphenyl-2-propen-1-one derivatives and ammonium acetate under solvent-free condition in the presence of silica-supported perchloric acid (HClO4–SiO2) is described. The catalyst is easily prepared, stable, reusable and efficient under the reaction conditions.

  在无溶剂的情况下，通过5,5-二甲基-1,3-环己二酮（二甲酮），1,3-二苯基-2-丙烯-1-酮衍生物和乙酸铵的汉茨反应轻松合成某些1,4-二氢吡啶衍生物描述了在二氧化硅负载的高氯酸（HClO 4 -SiO 2）存在的条件下。该催化剂在反应条件下易于制备，稳定，可重复使用和有效。
• Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents
  作者：Atul Kumar、Siddharth Sharma、Vishwa Deepak Tripathi、Ram Awatar Maurya、Swayam Prakash Srivastava、Gitika Bhatia、A.K. Tamrakar、Arvind Kumar Srivastava

  DOI：10.1016/j.bmc.2009.11.061

  日期：2010.6.1

  A series of 2,4-disubstituted polyhydroquinoline were synthesized and evaluated for their in vivo antihyperglycemic as well as antidyslipidemic activities. Several synthesized compounds have exhibited promising in vivo antihyperglycemic in SLM, STZ-S, and db/db mice model along with significant lipid and TG modulating activity. All these compounds were evaluated in various in vitro models of diabetes to know the possible mechanism of their antihyperglycemic action. Interestingly, compounds 3a-r (diaryl substitution) have exhibited promising protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity whereas, compounds 5a-d (acid substituted) have shown significant glycogen phosphorylase activity. (C) 2009 Published by Elsevier Ltd.
• Cobalt Nanoparticles Promoted Highly Efficient One Pot Four-Component Synthesis of 1,4-Dihydropyridines under Solvent-Free Conditions
  作者：Javad SAFARI、Sayed Hossein BANITABA、Shiva DEHGHAN KHALILI

  DOI：10.1016/s1872-2067(10)60295-1

  日期：2011.11

  A straightforward and general method has been developed for the synthesis of C(5)-unsubstitiuted 1,4-dihydropyridines by a reaction using dimedone, acetophenone, aromatic aldehydes, and ammonium acetate in the presence of a catalytic amount of Co nanoparticles as a heterogeneous and eco-friendly catalyst with high catalytic activity at room temperature under solvent-free conditions. This catalyst is easily separated by magnetic devices and can be reused without any apparent loss of activity for the reaction. In addition, it is very interesting that when using Co nanoparticles as a catalyst, spatially-hindered aldehydes such as 2-methoxy-, 2-fluoro-, and 2-chloro-aldehydes are suitable for this reaction.