1,1'-联-2-萘酚的合成研究及其拆分
采用氧化偶联法，以2-萘酚为原料，四甲基乙二胺碱式氯化铜配合物为催化剂，室温下反应合成外消旋联萘酚。通过IR和1HNMR对产物结构进行表征确定为所需物质。并得到最优的反应条件是当催化剂用量为5mol%的四甲基乙二胺碱式氯化铜配合物、反应时间2.5h、反应温度为常温。
以N-苄基辛可尼丁作为拆分剂，对外消旋的1,1'-联-2-萘酚进行拆分。利用R-联萘酚与N-苄基辛可尼丁形成的复合物与S-联萘酚溶解度的差异进行分离提纯，分别得到R-联萘酚和S-联萘酚，并且得出只用乙酸丁酯作为拆分溶剂可大大提高拆分效率。
毕业论文关键词：1,1'-联-2-萘酚；四甲基乙二胺碱式氯化铜配合物；氧化偶合；红外光谱；核磁共振
Study on synthesis and Resolution of 2, 2′ - dihydroxy- 1, 1′-dinaphthalene
ABSTRACT: 1,1 ' - bi-2-naphthol are a class of optically active compounds having a chiral axis as excellent chiral source , such compounds have been widely used in chiral recognition and asymmetric organic synthesis reactions . This paper studies the 1,1 ' - bi-2-naphthol synthesis and resolution. Synthesis : the oxidative coupling method , 2-naphthol as a raw material , tetramethylethylenediamine, basic copper chloride complex catalyst , the reaction temperature synthesis of racemic binaphthol experimental study of the amount of catalyst , reaction time and temperature couplet naphthol yield and optimal reaction conditions are: the amount of catalyst 5mol% of tetramethylethylenediamine basic copper chloride complexes, reaction time 2.5h, the reaction temperature is room temperature . IR and HNMR through the structure of product characterization. Resolution : the n- benzyl kissin clothianidin as resolving agent , racemic 1,1 ' - bi-2 - naphthol resolution . use of R- binaphthol with benzyl n- octyl clothianidin complex formed with s- binaphthol difference solubility for separation and purification , were obtained R- and S-binaphthol binaphthol finally investigated single resolution factors affecting the efficiency of solvents on the resolution , draw only as a resolution with butyl acetate solvent can greatly improve the efficiency of the resolution .
Keyword: 1,1 ' - bi-2-naphthol；Cu（OH）Cl•TMEDA；oxidative coupling；IR；HNMR
目 录
第一章 绪论 - 1 -
1.1 引言 - 1 -
1.2 1,1'-联-2-萘酚的简介 - 1 -
1.3 联萘酚的应用 - 2 -
1.3.1 不对称还原反应 - 2 -
1.3.2 不对称氧化反应 - 3 -
1.4 联萘酚的合成 - 3 -
1.4.1 外消旋联萘酚的合成 - 4 -
1.4.2 不对称氧化偶联合成联萘酚 - 5 -
1.5 外消旋联萘酚的拆分 - 6 -
1.5.1 化学拆分 - 6 -
1.5.2 酶拆分 - 7 -
1.5.3 高效液相色谱法拆分 - 7 -
第二章 1, 1’ -联- 2-萘酚合成与拆分的方法研究 - 8 -
2.1 1, 1’ -联- 2-萘酚的合成方法 - 8 -
2.1.1 四甲基乙二胺碱式氯化铜配合物的合成方案 - 9 -
2.1.2 1,1'-联-2-萘酚的合成方案 - 9 -
2.2 1, 1’ -联- 2-萘酚的拆分方法 - 9 -