2-(3,4-二甲氧基苯基)-4-氧代-4H-色烯-3-基乙酸酯的晶体结构及旋光性
投稿时间:2018-01-06  修订日期:2018-02-01  点此下载全文
引用本文:张开霞,王朝明,金永生.2-(3,4-二甲氧基苯基)-4-氧代-4H-色烯-3-基乙酸酯的晶体结构及旋光性[J].药学实践杂志,2018,36(2):170~172,179
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张开霞 烟台大学新型制剂与生物技术药物研究山东省高校协同创新中心、教育部分子药理和药物评价重点实验室, 山东 烟台 264005
第二军医大学药学院, 上海 200433 
 
王朝明 烟台大学新型制剂与生物技术药物研究山东省高校协同创新中心、教育部分子药理和药物评价重点实验室, 山东 烟台 264005  
金永生 烟台大学新型制剂与生物技术药物研究山东省高校协同创新中心、教育部分子药理和药物评价重点实验室, 山东 烟台 264005
第二军医大学药学院, 上海 200433 
ysjinsmmu@163.com 
基金项目:上海市科委科技支撑项目(17001980803;12431900801)
中文摘要:目的 探讨具有降血脂作用的黄酮醇衍生物2-(3,4-二甲氧基苯基)-4-氧代-4H-色烯-3-基乙酸酯(4)晶体结构及旋光性。方法 采用X射线单晶衍射技术获得绝对构型及SGW®-1自动旋光仪测定化合物旋光性。结果 X射线单晶衍射表明化合物4属于正交晶系,P212121空间群,晶胞参数a=7.763(2)Å,b=13.930(4)Å,c=14.906(4)Å,α=β=γ=90.00°,V=1 611.91(8)Å3Z=8;该晶态下分子间不存在氢键联系,分子以范德华力维系其在空间的稳定排列。从单晶数据可以看出,化合物4中二甲氧基取代的苯环相对于4H-色烯骨架有33.9(2)°扭转,推测可能存在旋光性;进一步的旋光实验结果证明该化合物具有左旋光性,比旋光度为[α]D19.1=-5.077°。结论 从单晶结果可知,由于化合物4中,二甲氧基取代的苯环相对于4H-色烯骨架有33.9(2)°扭转,形成手性,化合物具有旋光性。这类非黄酮苷类黄酮具有旋光性,未曾见报道。
中文关键词:黄酮类化合物  X射线单晶衍射  旋光性
 
Crystal structure and optical activity of 2-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-3-yl acetate
Abstract:Objective To investigate the structure and optical activity of flavonoid derivative:2-(3,4-dimethoxyphenyl) -4-oxo-4H-chromen-3-yl acetate (4). Methods The absolute configuration was obtained by X-ray single crystal diffraction. The optical rotation of the compound was determined by the SGW® -1 automatic polarimeter. Results X-ray single crystal diffraction showed that compound 4 belongs to the orthorhombic space group P212121 with a=7.763 (2)Å, b=13.930 (4)Å and c=14.906 (4), α=β=γ=90.00°, V=1611.91 (8) Å3, Z=8. There is no hydrogen bonding between the molecules in this crystal state. The molecules maintain their stable arrangement in space by van der Waals forces. It can be seen from the single-crystal data that there is a 33.9 (2)° torsion of the dimethoxy-substituted benzene ring in the compound 4 with respect to the 4H-chromene skeleton, suggesting that there may exist optical activity. Further experimental results of the optical rotation proved that the compound has a L-rotatory, specific rotation[α]D19.1=-5.077°. Conclusion The results of the single crystal indicated that the benzene ring substituted with dimethoxy group in compound 4 has a 33.9 (2)° torsion relative to the 4H-chromene skeleton, which results in chirality and optical activity. This is the first report that non-flavonoid-glycoside has optical activity.
keywords:flavonoids  X-ray single crystal diffraction  optical activity
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