4-(4-fluorophenyl)-7,7-dimethyl-2-phenyl-4,6,7,8-tetrahydro-5(1H)-quinolinone | 1233334-59-2

• 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-(4-fluorophenyl)-7,7-dimethyl-2-phenyl-4,6,7,8-tetrahydro-5(1H)-quinolinone
• 英文别名: 4-(4-fluorophenyl)-7,7-dimethyl-2-phenyl-4,6,7,8-tetrahydroquinolin-5(1H)-one；4-(4-Fluorophenyl)-7,7-dimethyl-2-phenyl-1,4,6,8-tetrahydroquinolin-5-one
• CAS: 1233334-59-2
• 化学式: C₂₃H₂₂FNO
• 分子量: 347.432
• InChiKey: MCYIOUSRIOOVQR-UHFFFAOYSA-N

物化性质

• 沸点：
  511.9±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-7,7-dimethyl-2-phenyl-4,6,7,8-tetrahydro-5(1H)-quinolinone 在 双氧水 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以82.3%的产率得到4-(4-fluorophenyl)-7,7-dimethyl-2-phenyl-7,8-dihydroquinolin-5(6H)-one
  参考文献：
  名称：

  Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.11.061
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 4-fluorochalcone 在 ammonium acetate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.3h， 以92.7%的产率得到4-(4-fluorophenyl)-7,7-dimethyl-2-phenyl-4,6,7,8-tetrahydro-5(1H)-quinolinone
  参考文献：
  名称：

  Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.11.061

文献信息

• 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.
• 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.