7,7-dimethyl-4-(4-methylphenyl)-5-oxo-2-phenyl-1,4,5,6,7,8-hexahydroquinoline

• 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-methylphenyl)-5-oxo-2-phenyl-1,4,5,6,7,8-hexahydroquinoline
• 英文别名: 7,7-dimethyl-5-oxo-2-phenyl-4-(4-methylphenyl)-1,4,5,6,7,8-hexahydroquinoline；7,7-dimethyl-2-phenyl-4-(4-methylphenyl)-1,4,5,6,7,8-hexahydroquinoline-5-one；7,8-dihydro-7,7-dimethyl-2-phenyl-4-p-tolylquinolin-5(1H,4H,6H)-one；7,7-dimethyl-2-phenyl-4-p-tolyl-4,6,7,8-tetrahydroquinolin-5(1H)-one；7,7-Dimethyl-2-phenyl-4-(4-methylphenyl)-1,4,5,6,7,8-hexahydroquinoline-5-one；7,7-dimethyl-4-(4-methylphenyl)-2-phenyl-1,4,6,8-tetrahydroquinolin-5-one
• 化学式: C₂₄H₂₅NO
• 分子量: 343.469
• InChiKey: BJCLIDNHSWKGJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以85%的产率得到7,7-dimethyl-4-(4-methylphenyl)-5-oxo-2-phenyl-1,4,5,6,7,8-hexahydroquinoline
  参考文献：
  名称：

  二氧化硅负载的高氯酸（HClO 4 -SiO 2）：一种温和，可重复使用且高效的非均相催化剂，可通过不对称的Hantzsch反应多组分合成1,4-二氢吡啶

  摘要：

  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。

  DOI：

  10.1007/s11164-012-0968-0

文献信息

• 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.
• Hu, Xueyuan; Zhang, Xinying; Fan, Xuesen, Journal of Chemical Research, 2005, # 11, p. 697 - 699
  作者：Hu, Xueyuan、Zhang, Xinying、Fan, Xuesen、Qu, Guirong、Li, Yanzhen

  DOI：——

  日期：——
• A facile and expeditious microwave-assisted synthesis of 4-aryl-2-ferrocenyl-quinoline derivatives via multi-component reaction
  作者：Shu-Jiang Tu、Shu Yan、Xu-Dong Cao、Shan-Shan Wu、Xiao-Hong Zhang、Wen-Juan Hao、Zheng-Guo Han、Feng Shi

  DOI：10.1016/j.jorganchem.2008.10.007

  日期：2009.1

  An efficient and rapid route for the synthesis of 4-aryl-2-ferrocenyl-quinoline derivatives through microwave-assisted multi-component reaction of acetylferrocene with aromatic aldehyde and dimedone in the presence of ammonium acetate using DMF as reaction media at 100 degrees C is described. This novel procedure lends itself well to combinatorial methods, providing the target heteropolymetallic compounds in excellent yield without further purification. (C) 2008 Elsevier B.V. All rights reserved.
• 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.