CAJ | 학술논문

在合成松香基手性试剂(4a~4f)的过程中，首次发现N-(1-萘基)-马来海枞酸二酰亚胺(4f)的位阻异构现象，而与其结构类似的N-苯基-马来海枞酸二酰亚胺(4a)、 N-(2-羧基苯基)-甲酯化马来海松酸二酰亚胺(4b)、N-(2-硝基苯基)-甲酯化马来海松酸二酰亚胺(4c)、 N-(2-氯苯基)-甲酯化马来海松酸二酰亚胺(4d)和N-[1-(2-氨基)-苯基]-甲酯化马来海松酸二酰亚胺(4e)则没有该位阻异构现象。化合物4a~4f的结构通过核磁共振、质谱和红外光谱等方法进行了表征。采用变温条件下的1 H NMR谱图研究了化合物4f的位阻异构化动力学特性。
재합성송향기수성시제(4a~4f)적과정중，수차발현N-(1-내기)-마래해종산이선아알(4f)적위조이구현상，이여기결구유사적N-분기-마래해종산이선아알(4a)、 N-(2-최기분기)-갑지화마래해송산이선아알(4b)、N-(2-초기분기)-갑지화마래해송산이선아알(4c)、 N-(2-록분기)-갑지화마래해송산이선아알(4d)화N-[1-(2-안기)-분기]-갑지화마래해송산이선아알(4e)칙몰유해위조이구현상。화합물4a~4f적결구통과핵자공진、질보화홍외광보등방법진행료표정。채용변온조건하적1 H NMR보도연구료화합물4f적위조이구화동역학특성。
During the last few years, considerable interest has been focused on the atropisomerism of N-aryl bond contain compounds which belong to one of the most common classes with atropisomers. Six N-aryl methyl maleopimaric acid diimides ( 4 a-4 f ) were synthesized from aromatic amines andmaleopimaric acid trimethyl ester(3). The structures of the compounds were characterized by 1H NMR,13C NMR and MS. The atropiso-merism and kinetics analyses of the N-(1-naphthyl) maleopimaric acid diimides were carried out by 1 H NMR. In the course of preparing resin-based chiralregent, atropisomerism was found in N-(1-naphthy) maleopimaric acid diimides(4f). The N-(1-phenyl) maleopimaric acid diimide(4a), N-(2-carboxy phenyl) methyl ma-leopimaric acid diimide ( 4 b ) , N-( 2-nitrophenyl )-methyl maleopimaric acid diimide ( 4 c ) , N-( 2-chlorophe-nyl)-methyl maleopimaric acid diimide(4d) and N-[1-(2-amine)-phenyl]-methyl maleopimaric acid diimide (4e) did not exist atropisomerism due to the smaller steric effects. The results indicated that maleopimaric N-naphthylimide ( 4 f ) underwent slow trans-cis conversion and induced in a gradual change of different [ trans]/[ cis] ratio during dissolution in CDCl3 at ambient temperature.