Crystal structure and optical activity of 2-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-3-yl acetate
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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)Å3,Z=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。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.
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Key words:
- flavonoids /
- X-ray single crystal diffraction /
- optical activity
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[1] 陈白灵.黄酮类化合物的药理活性研究新进展[J].海南医学,2012,23(9):119-121. [2] 刘星雨,周敏,孙体健.天然黄酮类化合物的药理活性及分离提取[J].中国药物与临床, 2014, 14(5):621-624. [3] 唐栩,许东辉,梅雪婷,等.26种黄酮类天然活性成分的药理研究进展[J].中药材, 2003, 26(1):46-54. [4] 李荣,李俊.黄酮类化合物药理活性及其构效关系研究进展[J].安徽医药,2005, 9(7):481-483. [5] 金永生, 姜远英, 吴秋业, 等.具有降脂作用的3-取代氧基-3',4'-二甲氧基黄酮类化合物[P]. 101244057A.2008-08-20. [6] 梅青刚, 袁伟成, 王淳.黄酮醇类化合物的合成研究进展[J].有机化学, 2015, 35(1):70-84.
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