3-（2-对甲苯基乙烯基）-5（4H）-异噁唑酮的合成、晶体结构、^1H NMR及其异构化研究  

Synthesis, Single Crystal Structure and ~1H NMR Characterization of 3-(2-p-Methylphenylvinyl)-5(4H)-isoxazolone and Theoretical Study for Its Isomerization

作　　者：黄坤林[1] 李彩今[2] 刘群[1] 白洪涛[2] 牟忠诚[1] 

机构地区：[1]东北师范大学化学学院,长春130024 [2]吉林大学化学学院,长春130023

出　　处：《高等学校化学学报》2004年第7期1264-1267,MJ03,共5页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金 (批准号 :2 0 2 72 0 0 8);教育部科学技术研究重点项目 (批准号 :0 3 0 5 9)资助

摘　　要：采用甲硫酯与 NH2 OH· HCl在室温条件下反应 ,合成了 3 -( 2 -对甲苯基乙烯基 ) -5 ( 4 H ) -异唑酮 ,通过单晶 X射线衍射确定了产物的结构 .由 1 H NMR确定的构型与晶体结构完全一致 ,表明标题化合物在弱极性溶剂 (如乙醚和氯仿 )中是稳定的 .半经验 AM1和 PM3计算的 C7和 C8净电荷 (分别为 -0 .0 77,-0 .1 0 1 )可能是 H7和 H8化学位移 (分别为 6.83和 6.96)很接近的主要原因 .B3 LYP/6-3 1 1 G* *基组计算的异构体能量数据表明 ,3 -( 2 -对甲苯基乙烯基 ) -5 ( 4 H)p-Methylphenylvinyl)-5(4H)-isoxazolone was synthesized by the reaction of methylthio ester with NH 2OH·HCl at room temperature and its structure was characterized by single crystal X-ray diffraction. The configuration based on 1H NMR spectrum in CDCl 3 is in agreement with the crystal structure, which indicates that the titled compound is stable in poorly polar solvents, such as diethyl ether and CHCl 3. For 3-(p-methylphenylvinyl)-5(4H)-isoxazolone, the net-charge of C7 is -0.077 and that of C8 is -0.101 by semi-experiential calculations with AM1 and PM3 methods, which are responsible for the chemical shift of H7(6.83) and H8(6.96). With the B3LYP/6-311G ** calculation, the 3-(p-Methylphenylvinyl)-5(4H)-isoxazolone is the most stable configuration among the three isomers.

关 键 词：3-(2-对甲苯基乙烯基)-5(4H)-异噁唑酮 合成 晶体结构 核磁共振 异构化 

分 类 号：O626.24[理学—有机化学]