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有机化学 ›› 2004, Vol. 24 ›› Issue (6): 697-701. 上一篇    下一篇

研究简报

1,5-二甲基-2-(S)-(1′-苯基乙基)-2-氮杂-8-氧杂-双环[3.3.0]辛烷-3,7-二酮的合成及其结构表征

胡炳成*, 吕春绪   

  1. 南京理工大学化工学院 南京 210094
  • 收稿日期:2003-09-01 修回日期:2003-11-17 接受日期:2003-12-30 发布日期:2022-09-21
  • 通讯作者: *E-mail: hubingcheng@yahoo.com

Synthesis and Structural Characterization of 1,5-Dimethyl-2-(S)-(1′-phenylethyl)-2-aza-8-oxa-bicyclo[3.3.0]octane-3,7-dione

HU, Bing-Cheng*, LÜ, Chun-Xu   

  1. School of Chemical Engineering, Nanjing University of Science & Technology,Nanjing 210094
  • Received:2003-09-01 Revised:2003-11-17 Accepted:2003-12-30 Published:2022-09-21

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利用2,3-丁二酮与丙二腈缩合形成双甲基双氰基环并内酰胺,经酸性水解得到双甲基环并内酯,然后和(S)-(-)-(1-苯基乙基)胺反应生成1,5-二甲基-2-(S)-(1′-苯基乙基)-2-氮杂-8-氧杂-双环[3.3.0]辛烷-3,7-二酮,通过元素分析、红外光谱、核磁共振氢谱和质谱对其结构进行了表征.用X射线单晶衍射法测定了目标产物的晶体结构,结果表明,晶体属单斜晶系,P21空间群,a=0.8777(18) nm, b=1.0102(2) nm, c=0.9009(18) nm, β=118.75(3)°,V=0.7003(2) nm3, Dc=1.296 g·cm－3, μ=0.089 mm－1, F(000)=292, Z=2, R1=0.0393, wR2=0.0955.

关键词: 双甲基双氰基环并内酰胺, 双甲基环并内酯, (S)-(-)-(1-苯基乙基)胺, X射线衍射

1,5-Dimethyl-2-(S)-(1′-phenylethyl)-2-aza-8-oxa-bicyclo[3.3.0]octane-3,7-dione was synthesized. The reaction of 2,3-butanedione with malononitrile gave dimethyldicyano-bicyclolactam. Under acidic condition the lactam was hydrolyzed to dimethylbicyclolactone, which was converted with (S)-(-)-(1-phenylethyl)-amine into the target product. Thestructure was characterized by elemental analysis, IR, 1H NMR and MS spectra. The crystal structure was determined by single-crystal X-ray diffraction analysis. The crystal belongs to monoclinic system with space group P21, unit cell dimensions: a=0.8777(18) nm, b=1.0102(2) nm, c=0.9009(18)nm, β=118.75(3)°, V=0.7003(2) nm3, Dc=1.296 g·cm－3, μ=0.089 mm－1, F(000)=292, Z=2, R1=0.0393, wR2=0.0955.

Key words: dimethyldicyanobicyclolactam, dimethylbicyclolactone, (S)-(－)-(1-phenylethyl)-amine, X-ray diffraction