C2对称手性L-脯氨醇方酰胺的合成与晶体结构

Synthesis and crystal structure of chiral L-prolinol squaramides with C2-symmetry

以廉价易得的方酸为原料,通过酯化,再与L-脯氨醇发生氨解反应,得到具有C2对称结构的手性L-脯氨醇方酰胺(分子式:C14H20N2O4),两步反应总收率67.5%.其结构经FT-IR、1 H NMR、13 C NMR、ESI-HRMS以及X-射线单晶衍射进行确证.该晶体属于斜方晶系,P212121空间群,晶胞参数:a=0.807 04(12)nm,b=0.901 36(13)nm,c=2.059 6(3)nm,α=β=γ=90.00°,V=1.498 2(4)nm3,Z=4,Dc=1.323g·cm-3,μ=0.100 mm-1,F(000)=640,最终残差因子R1=0.042 9,wR2=0.103 9.

Starting form readily available squaric acid,an efficient method for the synthesis of chiral Lprolinol squaramides with C2-symmetry was described,involving esterification reaction and ammonolysis reaction with chiral L-prolinol to give the title compound(C14H20N2O4)in a total yield of67.5%.Moreover,the structures of the target compound and intermediate were confirmed by FT-IR,1 H NMR,13 C NMR,ESI-HRMS and X-ray diffraction analysis.The crystal of the title compound belongs to orthorhombic system in a space group of P212121,with a=0.807 04(12)nm,b=0.901 36(13)nm,c=2.059 6(3)nm,α=β=γ=90.00°,V=1.498 2(4)nm3,Z=4,Dc=1.323 g·cm-3,μ=0.100 mm-1,F(000)=640,R1=0.042 9,wR2=0.103 9.