4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-芳氨基噻唑的合成、晶体结构及杀虫活性  

Synthesis,Crystal Structure and Insecticidal Activity of 4-(7-Methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)N-(aryl)thiazol-2-amine

作　　者：罗先福[1] 胡艾希[1] 王宇[1,2] 叶姣[1] 王晓光[2] 欧晓明[2] 

机构地区：[1]湖南大学化学化工学院,长沙410082 [2]湖南化工研究院,长沙410007

出　　处：《高等学校化学学报》2011年第12期2800-2805,共6页Chemical Journal of Chinese Universities

基　　金：国家科技支撑计划项目(批准号:2011BAE06B01)资助

摘　　要：以2-(2-甲基烯丙氧基)苯酚为原料,经Claisen重排、呋喃环化、醚化、Friedel-Crafts乙酰化、α-溴代和噻唑环化等反应合成了22种4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-芳氨基噻唑化合物.化合物的结构经质谱、1H NMR和元素分析等确证.采用单晶X射线衍射仪测定了化合物7j的晶体结构,该晶体属于单斜晶系,空间群为C2/c,晶胞参数a=2.21140(12)nm,b=0.87602(5)nm,c=2.13911(12)nm,β=115.5380(10)°;V=3.7391(4)nm3,Z=8,Dc=1.375 g/cm3,F(000)=1616,S=1.046,μ=0.333 mm-1,最终偏差因子R1=0.0390,wR2=0.1079.杀虫活性实验结果表明,化合物7a,7b,7h和7t在浓度为500mg/L时对蚕豆蚜死亡率分别为95.12%,62.60%,57.53%和59.06%.In order to find novel insecticides with high activity,a series of 4-（7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl）-N-（aryl）thiazol-2-amines was synthesized from 2-（2-methylallyloxy）phenol with Claisen rearrangement,cyclization of furan,etherification,Friedel-Crafts acylation,α-bromation and cyclization of thiazole.Their structures were confirmed by mass spectrometry（MS）,^1H NMR spectra and elemental analysis.The crystal structure of compound 7j was determined by X-ray diffraction analysis.The crystal belongs to the monoclinic system,space group C2/c with a=2.21140（12） nm,b=0.87602（5） nm,c=2.13911（12） nm,β=115.5380（10）°;V=3.7391（4） nm^3,Z=8,Dc=1.375 g/cm^3,F（000）=1616,S=1.046,μ=0.333 mm^-1,the final R1=0.0390 and wR2=0.1079.The preliminary bioassays indicated that compound 7a,7b,7h and 7t exhibited insecticidal activity against Aphis fabae were 95.12%,62.60%,57.53% and 59.06%,respectively,at 500 mg/L.

关 键 词：4-(7-甲氧基-2 2-二甲基-2 3-二氢苯并呋喃-5-基)-2-芳氨基噻唑 杀虫活性 晶体结构 

分 类 号：O626.2[理学—有机化学]