1,3-偶极环加成反应构建四氢吡咯螺吲哚衍生物及其结构表征

1,3-Dipolar cycloadditions for the synthesis of spirooxindole-based tetrahydropyrroles and its crystal structure characterization

以N-苄基靛红、氨基丙二酸二乙酯和丙烯酸甲酯为原料,在甲苯溶剂中,通过消旋磷酸的催化,在常温搅拌下即可一步合成得到化合物C_(26)H_(28)N_2O_7,实现了多官能团化的四氢吡咯螺吲哚衍生物骨架的构建.其结构通过单晶X射线衍射法确定,晶体属三斜晶系,空间群为P-1,相对分子质量Mr=480.50,晶胞参数a=0.895 73(3)nm,b=0.956 10(2)nm,c=1.503 61(3)nm,V=1.252 31(6)nm^3,Z=2,晶胞密度Dc=1.274g/cm^3,吸收系数μ=0.771mm^(-1),单胞中电子的数目F(000)=508.晶体结构用直接法解出,经全矩阵最小二乘法对原子参数进行修正,最终的偏离因子R=0.070 7,wR=0.139 9.在晶体结构中新形成的四氢吡咯环为信封式构象,与吲哚环近似于垂直.

The compound C26H28N2O7 has been synthesized by the 1,3-dipolar reaction of N-benzyl isatin,amino-ester and methyl acrylate in toluene under stirring at room temperature catalyzed by racemic phosphoric acid,and achieved the construction of multi-functional spirooxindole-based tetrahydropyrroles skeleton.The structure was determined by single crystal X-ray diffraction.The crystal is triclinic,space group is P-1,with Mr=480.50,a = 0.895 73（3）nm,b = 0.956 10（2）nm,c=1.503 61（3）nm,V = 1.252 31（6）nm3,Z = 2,Dc= 1.274g/mm3,μ= 0.771mm-1,F（000）=508.The structure was solved by direct methods and refined by full-mat rix least squares method to the get final R=0.070 7,ωR =0.139 9.X-ray analysis reveals that the newly formed ring of tetrahydropyrrole in the crystal structure is envelope conformation,and it is similar vertical with indole ring.