木质素模型物紫丁香酚基丙三醇-β-愈创木基丙醚的合成与结构表征

Synthesis and Characterization of A Novel Lignin Model Compound Named Guaiacylglycerol-β-guaiacyl Ether

摘要: 以乙酰丁香酮为原料经溴代、取代、羟甲基化以及还原等反应,合成了一种新型的β-O-4型木质素模型物紫丁香酚基丙三醇-β-愈创木基丙醚(SG),并通过IR、 1H NMR、13C NMR 和HRMS以及X射线单晶衍射进行了结构鉴定和表征。X射线单晶衍射法测定表明,该化合物属三斜晶系,空间群为P-1,晶包参数a=0.724 20(14),b=1.077 0(2),c=1.205 4(2)nm,β=90.43(3)°,V=0.858 0(3)nm3,Z=2,Mr=350.36,F(000)=372,μ(MoKα)=0.104 mm-1,DC=1.356 g/cm3,λ=0.071 073 nm,R=0.0602,wR=0.162 1。另外,在晶体结构中分子间通过氢键作用形成二聚体结构。

Abstract: A novel lignin model compound named guaiacylglycerol-β-guaiacyl ether (SG) was synthesized from acetosyringone via bromination, substitution, hydroxyl methylation and reduction reaction. Its structure was characterized by FT-IR, 1H NMR, 13C NMR, HRMS and single-crystal X-ray diffraction. Single-crystal X-ray diffraction analysis showed that the compound was of triclinic system, space group P-1 with a=0.724 20(14), b=1.077 0(2), c=1.2054(2) nm, β=90.43(3)°, V=0.858 0(3) nm3, Z=2, Mr=350.36, F(000)=372, μ(MoKα)=0.104 mm-1, DC=1.356 g/cm3, λ=0.071 073 nm, the final R=0.060 2 and wR=0.162 1. In addition, the dimer was formed through intermolecular hydrogen bonds in crystal packing of the title compound.