多环芳烃菲和荧蒽半抗原的制备及量化计算  

Preparation and Quantum Chemical Calculation of Polycyclic Aromatic Hydrocarbons Nanthrene and Fluoranthene Haptens

作　　者：刘媛媛 陈奇娜 潘学春 黄江春 李壹[2] 

机构地区：[1]东南大学成贤学院制药与化学工程学院,江苏南京210088 [2]南京工业大学食品与轻工学院,江苏南京211816

出　　处：《化学试剂》2017年第11期1205-1208,1215,共5页Chemical Reagents

基　　金：江苏省自然科学基金青年基金资助项目(BK-20130749);江苏省高校自然科学研究面上资助项目(17KJB150006);东南大学成贤学院青年教师科研发展基金资助项目(y0004)

摘　　要：以多环芳烃菲和荧蒽为原料,分别与丁二酸酐发生傅克酰基化反应,制备γ-羰基-2-菲丁酸和γ-羰基-3-荧蒽丁酸,再经黄鸣龙还原制备半抗原2-菲丁酸和3-荧蒽丁酸,产品结构经熔点、IR和1HNMR表征。采用量子化学计算优化两种半抗原的分子构型,获得前线轨道、能量、电子分布及稳定性等信息,辅助半抗原的设计和筛选,为制备高特异性人工抗原奠定了基础。Using polycyclic aromatic hydrocarbons phenanthrene and fluoranthene as starting materials,4-oxo-4-（ phenanthren-2-yl） butanoic acid and 4-（ fluoranthen-3-yl）-4-oxobutanoic acid were synthesized by the Friedel-Crafts acylation with dihydrofuran-2,5-dione,respectively. Then haptens 4-（ phenanthren-2-yl） butanoic acid and 4-（ fluoranthen-3-yl） butanoic acid were prepared via Huang Min-lon reduction. The structures were confirmed by melting point,IR and1 HNMR. The molecular configurations of haptens were optimized by quantum chemical calculation,and the frontier orbital energy,electronic distribution and stability were obtained.These parameters can assist the design and screening of hapten,and lay the foundation for the preparation of high specific antigen.

关 键 词：菲丁酸 荧蒽丁酸 傅克酰基化反应 黄鸣龙还原 量子化学计算 

分 类 号：O625.1[理学—有机化学]