2-氨基-3-氰基-4-(2’,4’-二氯苯基)-4H-萘并[1,2-b]吡喃的合成和晶体结构

Synthesis and Crystal Structure of 2-amino-3-ethoxycarbonyl -4-(2' ,4'-chlorophenyl)-4H-naphtho[1 ,2-b]chromene

标题化合物C22H17Cl2NO3的晶体由α-乙氧羰基-2,4-二氯肉桂腈、β-萘酚在TEBA存在下合成并经DMF与水的混合溶剂重结晶而得.其结构通过元素分析、IR和1HNMR进行了表征,用X射线单晶衍射法测定了该化合物的晶体结构.结果表明,晶体属于单斜晶系,P21/n空间群。a=1.450 5(2)nm,b=0.903 7(1)nm,c=1.491 3(2)nm,α=90°,β=101.21(1)°,γ=90°,Mr=414.27,V=1.917 5(4)nm3,Dc=1.435 g·cm-3,Z=4,μ(MoKα)=0.362 mm-1,F(000)=856.晶体结构用直接法解出,经全矩阵最小二乘法修正,最终偏离因子R=0.044 44,Rw=0.117 7.化合物分子中,原子C(1),C(2),C(3),C(4),C(5)和O(1)形成一个六元环,该六元环中C(1)-C(2)键长为0.134 6(3)nm,表明为双键.此六元环为船式构象.

The title compound (C22H17Cl2NO3) was obtained by the reaction of α-ethoxycarbonyl-2,4-chlorocinnamonitrile and 2-naphthol in water in the presence of TEBA and by recrystallization from DMF and water. Its structure was characterized by elemental analysis, IR, 1HNMR and X-ray single crystal diffraction. The crystal belongs to monoclinic system, P21/n space group with a = 1. 450 5(2) nm,b=0. 903 7(1) nm,c=1. 491 3(2) nm,α=90°,β=101. 21(1)°,γ=90°,Mr = 414. 27,V = 1.917 5(4) nm3,Dc = 1. 435 g·cm-3 ,Z=4,μ(MoKα) =0. 362 mm-1 ,F(000) = 856. The structure was solved by direct methods and refined by full-matrix least squares method to the final R = 0.04444,Rw= 0.117 7. X-ray analysis reveals that atoms C(1), C(2), C(3), C(4), C(5) and O(1) form a six-membered ring in which the distance of C(1)-C(2) is 0. 134 6(3) nm, which show that it is a C=C double bond. In addition, the conformation of this six-membered ring is a boat form.