3-(取代基苯基)雪梨酮的合成及其核磁共振光譜之研究

Studies on the Synthesis of 3-(Substitutedphenyl)sydnones and Their NMR-spectra

高藝嘉(I-Chia Kao) ； 張文昆(Wen-Kuen Chang) ； 田憲儒(Hsien-Ju Tien)

《化學》 49卷4期 (1991/12) Pp. 271-278

https://doi.org/10.6623/chem.1991037

摘要

合成三十三種3-(取代基苯基)雪梨酮，其中四種爲新化合物：即3-(間-胺基苯基)雪梨酮、3-(間-乙醯胺基苯基)雪梨酮、3-(間-三氰乙醯胺基苯基)雪梨酮和3-(對-三氟乙醯胺基苯基)雪梨酮。測試11種3-(對/間-羥基苯基)雪梨酮及3-(胺基苯基)雪梨酮衍生物的^1H-NMR和^(13)C-NMR光譜，並由其NMR光譜研判得知：3-(對/間羥基苯基)雪梨酮有生成分子間氫鍵的可能，而3-(鄰-胺基苯基)雪梨酮則可能形成分子內氫鍵。另測試28種3-(取代基苯基)雪梨酮的^1H-NMR光譜得知：如果以3-(苯基)雪梨酮的雪梨酮環第4碳上的氫δ-776 ppm爲標準，則於苯環上的取代基爲活化基時，雪梨酮環第4碳上的氫，其化學位移向高磁場移動；反之，去活化基時，則向低磁場位移。

並列摘要

Thirty-three kinds of 3-(substitutedphenyl) sydnones were prepared. But 3-(m-aminophenyl) syd-none, 3-(m-acet-amidophenyl) sydnone and 3-(m-/p-trifluoroacetamidophenyl)sydnone are new com- pounds. From the ^1H-NMR and ^(13)C-NMR spectra of eleven 3-(hydroxyphenyl)sydnones, 3-(aminophenyl)- sydnones and their derivertives , 3-(hydroxyphenyl) sydnones can form the intermolecular hydrogen bond, while 3-(o-aminophenyl)sydnone may be form the intramolecular hydrogen bond. If it takes the chemical shift value 7.76 ppm of the hydrogen which attached to C-4 position of sydnone ring in 3-phenylsydnone as standard, to inspect the ^1H-NMR spectra of 28 kinds of 3- (substitutedphenyl)sydnones, it may be noted that when the activing substituted group at 3-phenyl ring, the chemical shift of the hydrogen attached to C-4 shift upfield, while the deactiving substituted group shift downfield.