碱催化Aldol缩合反应制备丹皮酚衍生物及其晶体结构

Alkali-catalyzed Synthesis of the Paeonol Derivative by Aldol Condensation Reaction and Its Crystal Structure

探讨用碱催化通过Aldol缩合反应来制备丹皮酚的衍生物。常温下用碱催化使丹皮酚和4-硝基苯甲醛发生Aldol缩合反应,生成了一种新型的丹皮酚衍生物β-羟基-1-(2'-羟基-4'-甲氧基苯基)-β-(4-硝基苯基)-1-丙酮,产率高达77.34%,用紫外光谱、红外光谱、质谱并结合核磁共振的氢谱、碳谱以及135°DEPT谱综合表征其结构。用X-射线衍射技术分析该丹皮酚衍生物的单晶结构并确定其分子的构型和构象,β-羟基-1-(2'-羟基-4'-甲氧基苯基)-β-(4-硝基苯基)-1-丙酮属于单斜晶系中的p21/c空间群,晶胞参数a=0.874 9(15)nm、b=1.137 8(2)nm、c=1.554 0(3)nm、α=90.0°、β=106.5(8)°、γ=90°,晶胞体积为1.483 5(5)nm^3,晶胞个数为4个,密度为1.416 mg/cm^3。用碱催化可使丹皮酚和芳香醛通过Aldol缩合反应来制备丹皮酚衍生物。

To investigate the synthesis of a paeonol derivative by Aldol condensation reaction with alkali as the catalyst,a novel paeonol derivative named β-hydroxy-1-（2＇-hydroxy-4＇-methoxylphenyl）-β-（4-nitrophenyl）-1-propanone was synthesized with paeonol and 4-nitrobenzaldehyde by Aldol condensation reaction in alkaline medium at room temperature.Its yield reached 77.34%,its structure was characterized by UV,IR,MS and1 H-NMR,13 CNMR,135° DEPT.The crystal structure of β-hydroxy-1-（2＇-hydroxy-4＇-methoxylphenyl）-β-（4-nitrophenyl）-1-propanone was also characterized by X-ray structure analysis,its crystal belongs to space group p21/c in triclinic crystallographic system,and its cell parameters a = 0.874 9（15） nm,b = 1.137 8（2） nm,c = 1.554 0（3） nm,α = 90.0°,β = 106.5（8） °,γ = 90°,V = 1.483 5（5） nm^3,Z = 4,Dc= 1.416 mg/cm^3.The paeonol derivative was synthesized through Aldol condensation reaction with paeonol and aromatic aldehyde in alkaline medium.