氢化奎尼定衍生物的合成及其催化性能研究  

Synthesis and catalytic performance of hydroquinidine derivatives

作　　者：万玮 陈庆港 彭国颖 黄建平[1] 黄长干[1] WAN Wei;CHEN Qing-gang;PENG Guo-ying;HUANG Jian-ping;HUANG Chang-gan(College of Chemistry and Materials,Jiangxi Agricultural University,Nanchang Key Laboratory of Chemical Utilization of Plant Resources,Nanchang 330045,China)

机构地区：[1]江西农业大学化学与材料学院,南昌市植物资源化学利用重点实验室,江西南昌330045

出　　处：《化学研究与应用》2023年第3期620-625,共6页Chemical Research and Application

基　　金：国家自然科学基金项目(31760068)资助;江西省重点研发项目(911013470029)资助。

摘　　要：以价格较低的奎尼丁为原料,常压催化加氢后,采用全新的方法与1,4-二氯酞嗪、1,4-二氯苯并[G]-2,3-二氮杂萘和卤代芳烃进行偶联,合成了氢化奎尼定1,4-(2,3-二氮杂萘)二醚(8a)、氢化奎尼定1,4-(苯并[G]-2,3-二氮杂萘)二醚(8b)、氢化奎尼定1-萘醚(8c)、氢化奎尼定9-菲醚(8d)和对氯苯甲酸氢化奎尼丁酯(8e),并通过FT-IR和NMR进行表征确认其结构。选用(22E,24S)-5α-豆甾-2,22-烯-6-酮作为底物,对目标化合物进行催化性能的测试。结果表明,8b和8d的选择性更佳,ee值达到77.8%,且8b的反应时间仅需两天,回收率高达81.3%。Hydroquinidine 1,4-(2,3-naphthalene)diether(8a),hydroquinidine 1,4-(benzo[G]-2,3-naphthalene)diether(8b),hydroquinidine 1-naphthyl ether(8c),hydroquinidine 9-phenanthrene(8d)and hydroquinidine p-chlorobenzoate(8e)were synthesized using quinidine after catalytic hydrogenation,coupled with 1,4-dichlorophthalazine,1,4-dichlorobenzo[G]-2,3-naphthalene and halogenated aromatic hydrocarbons by a new method.They were characterized by FT-IR and NMR to confirm their structures.(22E,24S)-5α-Stigmasta-2,22-dien-6-one was selected as the substrate to test the catalytic performance of the target compound.The results showed that the selectivity of 8b and 8d was better,and the enantiomeric excess reached 77.8%,and the reaction time of 8b was only two days,and the recovery rate was as high as 81.3%.

关 键 词：Sharpless不对称双羟基化反应 二氢奎尼丁 氢化奎尼定衍生物 

分 类 号：O643.3[理学—物理化学]