3,3'-Br-1,1'-联-2-萘酚的合成与表征
毕业论文关键词：BINOL；衍生物；合成；手性
The synthesis of3, 3'- Br - 1，1'-bi-2-naphthanol
Abstract：Binaphthol was a class of aromatic compounds having an asymmetric axis C2, with a certain rigidity and stereoselectivity, and the optically active binaphthol derivative was effective chiral catalysts,were widely used in biomedicine, and other fields. This paper coupleted naphthol and its derivatives synthesis and development of a detailed narrative.The main raw material of the synthesis of3, 3 '- Br - 1，1'-bi-2-naphthanol were2,2'-dihydroxy-1,1'-binaphthalene (BINOL), pure liquid bromine, and chloromethyl methyl ether. Then design the experiment plan. The experiment steps were as follows. Through the split of R- BINOL and S- BINOL on hydroxyl protection, and then to halide the product (fluorine substitution at the 3,3' positions of 2,2'-dihydroxy-1,1'-binaphthalene (BINOL).Finally to take off protection for 3, 3 '- Br - 1，1'-bi-2-naphthanol, then carry on the purification, and characterized the product of 2, 2 '- Br - 1，1'-bi-2-naphthanol. Results expressed: hydroxyl protecting the product easier to get high yields, bromo was the rate controlling step of the experiment, a lower yield. NMR spectra showed that the resulting product was realy the desired product.The use of 1H NMR for intermediates and target products were characterized. And the use of single-factor method to optimize the reaction conditions, the yield and purity has been the ideal target compound.
Keywords: BINOL；Derivatives; Synthesis; Chirality
目录
第一章 绪论 1
1.1联萘酚的介绍 1
1.2联萘酚的发展进程 1
1.2.1 消旋体联萘酚的发展 1
1.2.2 光活性联萘酚的发展 2
1.2.3 联萘酚配合物的发展 3
1.3联萘酚及其衍生物的研究意义 5
1.4核磁共振仪的原理 6
第二章 联萘酚(BINOL)的合成方法 8
2.1 外消旋体BINOL的合成 8
2.1.1 三氯化铁作为氧化剂 8
2.1.2 铜(Ⅱ)作为氧化剂 9
2.1.3 O2作为氧化剂 9
2.2外消旋体BINOL的拆分 10
2.2.1 化学拆分 10
2.2.2 色谱拆分 10
2.2.3 酶拆分 11
2.3 不对称氧化偶联合成法 11
2.3.1 手性铜胺配合物作为氧化剂 11
2.3.2 钒配合物作为氧化剂 11
2.3.3 手性环境中三氯化铁作为氧化剂 12
2.3.4 手性环境中光催化氧化 12
2.3.5 其他 12
第三章 3,3'-Br-1,1'-联-2-萘酚的合成与表征 13
3.1 引言 13
3.2 实验部分 13
3.2.1 主要仪器 13
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