碱催化蒽醛和丹皮酚的Aldol缩合反应及产物晶体结构

Alkali-catalyzed synthesis of anthraldehyde and paeonol by aldol condensation reaction and its crystal structure

探讨在常温下用碱催化蒽醛和丹皮酚的Aldol缩合反应,制备新型的蒽醛衍生物。在常温下用碱催化可使蒽醛和丹皮酚反应生成一种α,β-不饱和羰基化合物,产率为74.30%。借助现代光谱技术紫外光谱、红外光谱、质谱结合核磁共振氢谱、碳谱和135°DEPT谱确定出该化合物为1-(2-羟基-4-甲氧基苯基)-β-(9-蒽)-α,β-不饱和丙烯酮。用单晶X射线衍射技术分析该化合物的晶体结构并分析其分子的构型和构象,1-(2-羟基-4-甲氧基苯基)-β-(9-蒽)-α,β-不饱和丙烯酮属于单斜晶系中的P21/c空间群,晶胞参数:a=1.034 04(13)nm、b=1.370 22(18)nm、c=1.303 01(17)nm、α=90.0°、β=97.835(2)°、γ=90°,晶胞体积为1.829(4)nm3,晶胞个数4个,密度为1.287 mg/cm3。用碱催化能促使蒽醛和丹皮酚发生Aldol缩合反应,产物分子中新产生的碳碳双键属于E构型。

A α,β-unsaturated carbonyl compound,being a peace of anthraldehyde derivative,was synthesized with anthraldehyde and paeonol by aldol condensation reaction in alkali catalysis solution under room temperature,and based on the principle of aldol condensation reaction,its yield reached up to 74. 30%. The compound structure named 1-（ 2-hydroxy-4-methoxy phenyl）-β-（ 9-anthracene）-α,β-unsaturated carbonyl acrylic ketone had been characterized by UV,IR,MS and NMR including1 H-NMR,13 C-NMR,135° DEPT.The crystal structure of 1-（ 2-hydroxy-4-methoxy phenyl）-β-（ 9-anthracene）-α,β-unsaturated carbonyl acrylic ketone was also identified by X-ray diffraction technique,and its crystal belongs to space group P21/c in monoclinic crystallographic system,and its cell parameters： a = 1. 034 04（ 13） nm、b = 1. 370 22（ 18） nm,c =1. 303 01（ 17） nm,α = 90. 0°,β = 97. 835（ 2） °,γ = 90°,V = 1. 829（ 4） nm3,Z = 4,Dc= 1. 287 mg/cm3.The anthraldehyde derivative was synthesized by aldol condensation reaction with anthraldehyde and paeonol aromatic aldehyde in alkali catalysis solution,and the configuration of newly produced carbon-carbon double bond is entgegen in its molecule structure.