一锅法合成新型7-苯基-1,4,5,6,7,8-六氢喹啉酮衍生物 |
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引用本文: | 刘燕,刘庆俭.一锅法合成新型7-苯基-1,4,5,6,7,8-六氢喹啉酮衍生物[J].合成化学,2016,24(11):982-986. |
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作者姓名: | 刘燕 刘庆俭 |
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作者单位: | 山东师范大学 化学化工与材料科学学院,山东 济南 250014 |
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摘 要: | 以5-苯基-1,3-环己二酮,醛,乙酰乙酸乙酯(或乙酰丙酮)和乙酸铵为原料,在无水乙醇中经一锅反应合成了14个新型的7-苯基-1,4,5,6,7,8-六氢喹啉酮衍生物,总收率85%~95%,其结构经1H NMR, 13C NMR, IR和HR-MS表征。采用X-ray单晶衍射研究了2-甲基-4,7-二苯基-5-氧代-1,4,5,6,7,8-六氢喹啉顺反异构体(5a和5a′)的晶体结构。结果表明:5a空间群为C2/c, a=9.458 35(19) ,b=19.789 0(4) ,c=11.040 9(2) , α=90°, β=105.614(2)°, γ=90°,V=1 990.28(7) 3, Z=4, μ=0.673 mm-1, F(000)=824; 5a′空间群为C2/c, a=9.770 2(5) , b=19.981 0(10) , c=10.430 1(4) , α=90°, β=98.361(5)°, γ=90°, V=2 014.51(17) 3, Z=4, μ=0.665 mm-1, F(000)=824。
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关 键 词: | 5-苯基-1 3-环己二酮 乙酰乙酸乙酯 7-苯基-1 4 5 6 7 8-六氢喹啉酮 一锅法 合成 |
收稿时间: | 2016-03-15 |
One-pot Method for Synthesis of Novel 7-Phenyl-1 ,4 ,5 ,6 ,7 ,8-hexahydroquinolinone Derivatives |
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Abstract: | Fourteen 7-phenyl-1,4,5,6,7,8-hexahydroquinolinone derivatives, in total yields of 85%~95%, were synthesized by one-pot method in EtOH, using 5-phenyl-1,3-cyclohexanedione, alde-hydes, ethyl acetoacetate ( or acetylactone ) and ammonium acetate as the materials. The structures were characterized by 1 H NMR, 13 C NMR, IR and HR-MS. The crystal structures of ethyl 4,7-diphen-yl-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinolin-3-carboxylate(5a and 5a′) were investigated by X-ray single crystal diffraction. The results indicated that 5a belongs to space group C2/c with a =9. 45835(19) ?, b=19. 7890(4) ?, c=11. 0409(2) ?, α=90°, β=105. 614(2)°, γ=90°, V=1990. 28(7) ?3 , Z=4,μ=0. 673 mm-1 , F(000) =824. 5a′belongs to space group C2/c with a=9. 7702(5) ?, b=19. 9810(10) ?, c=10. 4301(4) ?,α=90°,β=98. 361(5)°,γ=90°, V=2014. 51(17) ?3 , Z=4,μ=0. 665 mm-1 , F(000) =824. |
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Keywords: | 5-phenyl-1 3-cyclohexanedione ethyl acetoacetate 7-phenyl-1 4 5 6 7 8-hexahydro-quinolinone derivative one-pot method synthesis |
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