6b,11b-二羟基-9,9-二甲基-7-对甲氧基苯基-8,9,10,11b-四氢化6bH-苊并[1,2-b]吲哚-11(7H)-酮的合成和晶体结构

Synthesis and crystal structure of 6b,11b-dihydroxy-7-aryl-8,9,10,11b-tetrahydroacenaphtho[1,2-b]indol-11(7H)-one

利用L-脯氨酸催化的烯胺酮(1)与苊醌(2)的加成、环化串联反应,合成得到了6b,11b-二羟基-9,9-二甲基-7-对甲氧基苯基-8,9,10,11b-四氢化6bH-苊并[1,2-b]吲哚-11(7 H)-酮(3).标题化合物的结构通过单晶X射线衍射法确定,晶体属于单斜晶系,空间群C2/c,相对分子质量Mr=427.48,晶胞参数a=3.1870(6)nm,b=0.97422(19)nm,c=1.3648(3)nm,V=4.2344(15)nm3,Z=8,晶胞密度Dc=1.341g·cm-3,吸收系数μ=0.090mm-1,单胞中电子的数目F(000)=1808.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,最终的偏离因子为R=0.0957,wR=0.2724.在晶体结构中2个羟基处于顺式,通过分子间氢键形成二聚体.

The title compound 6 b,11 b-dihydroxy-7-aryl-8,9,10,11 b-tetrahydroacenaphtho[1,2-b]indol-11(7 H)-one derivatives(3)has been synthesized by the tandem reaction of enaminones and acenaphthequinone catalyzed by L-proline.The structure of compound3 was determined by single crystal X-ray diffraction analysis.The crystal is monoclinic,space group C2/c,with Mr=427.48,a=3.1870(6)nm,b=0.97422(19)nm,c=1.3648(3)nm,V=4.2344(15)nm3,Z=8,Dc=1.341 g·cm-3,μ=0.090 mm-1,F(000)=1808.The structure was solved by direct methods and refined by full-matrix least squares method to the final R=0.0957,wR=0.2724.X-ray analysis reveals that two hydroxy groups are in cis form.The dimer was formed by intermolecular hydrogen bonds in the molecule.