手性丙氨酸修饰的间苯二酚杯[4]芳烃化合物的合成、表征及水溶性分析  

Synthesis,Characterization and Analysis of Water Solubility of Resorcinol Calix[4]arenes Modified by Chiral Alanine

作　　者：周新民 王晴 陈禄思 贾爱铨[1] 张千峰[1] ZHOU Xinmin;WANG Qing;CHEN Lusi;JIA Aiquan;ZHANG Qianfeng(Institute of Molecular Engineering and Applied Chemistry,Anhui University of Technology,Maanshan 243002,China)

机构地区：[1]安徽工业大学分子工程与应用化学研究所,安徽马鞍山243002

出　　处：《安徽工业大学学报（自然科学版）》2023年第4期415-421,共7页Journal of Anhui University of Technology（Natural Science）

基　　金：国家自然科学基金项目(90922008)。

摘　　要：以间苯二酚为原料,合成C-乙基间苯二酚杯[4]芳烃(1a)、C-正丙基间苯二酚杯[4]芳烃(1b)和C-异丁基间苯二酚杯[4]芳烃(1c)等3种间苯二酚杯[4]芳烃化合物;以此为底物,在C-2位置引入水溶性手性丙氨酸,相继合成C-乙基-四亚甲基L-丙氨酸间苯二酚杯[4]芳烃(2a)、C-正丙基-四亚甲基L-丙氨酸间苯二酚杯[4]芳烃(2b)和C-异丁基-四亚甲基L-丙氨酸间苯二酚杯[4]芳烃(2c)3种水溶性化合物。通过核磁氢谱、红外光谱和元素分析对6种化合物的结构进行表征,且对两类化合物的水溶性进行比较分析。结果表明:红外光谱特征峰、核磁氢谱峰与化合物结构相符合;杯芳烃化合物在常温和40℃纯水中的pH基本不发生变化,维持在6.50左右;与之相比,水溶性化合物的pH有明显的下降趋势,随桥烷基取代基支链的缩短水溶性逐步提高,化合物2a的pH常温下达5.35,40℃下达4.50,水溶液中氢离子浓度增加近2个数量级,引入丙氨酸可极大提高杯芳烃化合物的水溶性。Taking resorcinol as raw material,three kinds of resorcinol calix[4]aromatic compounds of C−ethyl resorcinol calix[4]arene(1a),C−n−propyl resorcinol calix[4]arene(1b)and C−iso−butyl resorcinol calix[4]arene(1c)were synthesized.With three raw materials as the substrates,water-soluble alanine was introduced at the position of C−2,and three kinds of water-soluble compounds of C−ethyl tetramethylene L−alanine resorcinol calix[4]arene(2a),C−n−propyl−tetramethylene L−alanine resorcinol calix[4]arene(2b)and C−iso−butyl tetramethylene L−alanine resorcinol calix[4]arene(2c)were successively synthesized.The structures of six kinds of compounds were characterized and analyzed through FT−IR,1H NMR and elemental analysis,and the water solubility of two types of compounds was compared and analyzed.The results show that the characteristic infrared peak signal and nuclear magnetic resonance peak signal are consistent with the molecular structures of six kinds of compounds.The pH of calixarene compounds in pure water at room temperature and 40℃basically unchanged,maintaining about 6.50.Compared to this,the pH of water-soluble compounds shows a significant downward trend,and the water solubility gradually increaseswith the shortening of the bridging alkyl substituent chain.The pH of water-soluble compound 2a can reach 5.35 at room temperature and 4.50 at 40℃,the concentration of hydrogen ions in aqueous solution increases by nearly two orders of magnitude,and the introduction of alanine can greatly the water solubility of calixarene.

关 键 词：芳烃 手性丙氨酸 芳烃 水溶性 

分 类 号：O625[理学—有机化学]