缩醛酯在Perkin类反应中的形成及其晶体结构

THE FORMATION OF 1,1-DIACETATE DERIVATIVE IN PERKIN-TYPE REACTION AND THEIR CRYSTAL STRUCTURES

通过Perkin类反应得到3个新的化合物1,2和3.利用X-射线单晶衍射仪测定化合物1和2的晶体结构.实验表明:化合物1,(E)-2-{2′-[3″-(1″-乙酰基-吲哚)基]乙烯}基-8-羟基喹啉乙酸酯为单斜晶系,空间群为P2(1)/c,晶胞参数为:a=2.26566(9)nm,b=2.01990(8)nm,c=0.79445(3)nm,α=90°,β=90.715(2)°,γ=90°,V=3.6354(2)nm3,Z=8,Dc=1.353 mg/m3,μ=0.091 mm-1,F(000)=1552,R1=0.0526 andwR2=0.1409.化合物2,1-(1′,1′-二乙酰基)甲基苯并噻吩为斜方晶系,空间群为Pccn,晶胞参数为:a=1.70116(8)nm,b=2.00171(8)nm,c=0.76628(3)nm,α=90°,β=90°,γ=90°,V=2.60936(19)nm3,Z=8,Dc=1.345 mg/m3,μ=0.251 mm-1,F(000)=1 104,R1=0.0342 andwR2=0.0985.本文报道了这2个化合物的晶体结构.化合物1、2和3的形成表明,在这类Perkin反应中,酸的存在将导致缩醛酯的形成,从而降低了缩合产物的产率.

Three new compounds 1, 2 and 3 have been synthesized by Perkin - type condensation reaction. The crystal structures of compounds 1 and 2 were determined by X - ray single crystal diffraction. The experimental resuits show the following results. The compound 1, （E） - 2 - [ 2′ - （ 1″ - acetyl -^1H - indol - 3″ - yl） vinyl ] - quinolin - 8 - yl acetate, belongs to the monoclinic, space group P2 （ 1 ）/c with unit cell parameters a = 2. 265 66 （9） nm,b =2. 019 90（8） nm, c =0.794 45（3） nm, α =90°,β =90. 715（2）°,γ =90°, V=3. 635 4（2） nm3, Z =8, Dc = 1. 353 Mg/m3,μ=0. 091 mm^-1, F（000） = 1 552, R1 =0. 052 6 and wR2 =0. 140 9. The compound 2, 1,1 - Diacetoxy - 1 - （3′ - benzo [ b ] thinophene） methane, belongs to the orthorhombic, space group Pccn with unit cell parameters a=l.701 16（8） nm, b =2.001 71（8） nm, c=0.766 28（3） nm, α=90°, β=90°, γ= 90°, V=2. 609 36（19） nm^3, Z=8, Dc =1.345 Mg/m3,μ =0. 251 mm^-1, F（000） =1 104, R1 =0.034 2 and wR2 = 0. 098 5. The formation of compounds 1,2 and 3 show that the acidity in the Perkin type reaction will result in 1,1 - diacetate formation and reduce the yield of condensation products.