【作者】 陆秀琴；

【导师】 李景华；

【作者基本信息】 浙江工业大学 ， 药物化学， 2007， 硕士

【摘要】 手性氨基—羟基化合物作为重要手性配体和手性辅助试剂已经受到广泛和深入的研究。本文以手性氨基酚类化合物Betti碱及其衍生物为研究对象，完成Betti碱及其衍生物的合成与拆分，研究了由高效液相色谱手性固定相法拆分手性Betti碱及其衍生物对映体来测定其ee值，并且完成了对Betti碱及其衍生物和二羰基化合物缩合反应的研究。第二章中，我们使用手性柱，对Betti碱衍生物对映体进行了分离。通过条件的优化，确立Betti碱在流动相（V／V／V）CH₃OH∶CH₃CN∶25mmol／L K₂HPO₄=13∶12∶75，pH为7.5，流速为0.2mL／min。而Schiff碱和1-（α-吡咯烷基苄基）-2-萘酚的流动相则是（V／V）CH₃OH为25mmol／L K₂HPO₄（pH 7.5）=20∶8，pH为7.5，流速为1mL／min的条件下对映体分离情况较好。第三章中，合成并拆分了Betti碱，并对其与α-二羰基化合物和β-二羰基化合物反应进行了研究。室温条件下，乙二醛和Betti碱在甲醇中反应生成双缩合的Salen构型的Schiff碱9。在相同的条件下，乙酰丙酮和S-Betti碱反应生成了以烯醇式存在的缩合产物。第四章，我们用Betti碱盐酸盐及其衍生物和1，4-邻苯二甲醛或1，5-戊二醛在氰化钠存在下发生缩合反应，探讨了不同基团对反应结果的影响，得到了一系列14和17的Betti碱衍生物，产率都在78—89％之间。更多还原

【Abstract】 Chiral amino-hydroxy compounds, as a family of popular chiral ligands and chiral auxiliary reagents, have been studied widely. The thesis here described the chiral resolution of Betti Base and the synthesis of their derivatives. Also we researched the resolution of Betti base and their derivatives by high-performance liquid chromatography and chiral stationary phase method. Then, we do the research on the condensation reaction of Betti base with dicarbonyl compounds.In the chapter one, that was reviewed the preparation, resolution and application of the Betti base and their derivatives.In the chapter two, the condition of resolution of Betti base and its derivatives were established. The optimum condition was obtained that Betti Base can be baseline separated using mobile phase （V/V/V） CH₃OH: CH₃CN: 25 mmol/L K₂HPO₄=13:12:75, PH=7.5, flow rate is 0.2 mL/min. The optimum condition of 1-[phenyl[（E）-（phenylmethylene）amino]-methyl]-2-naphthalenol and 1-（-Pyrrolidinylbenzyl）-2-naphthol can be separated by using mobile phase of （V/V） CH₃OH为25 mmol/L K₂HPO₄ （pH 7.5）=20:8, PH=7.5, flow rate is lmL/min.In the chapter three, the derivatives of Betti base were synthesized and resoluted. Then their potential applications withα,β-dicarbonyl we were studied. At room temperature, A new tetradentate Schiff base ligand 9 that has similar type to Salen through condensation reaction was prepared by 40% glyoxal and Betti base in methanol. A new Schiff base was synthesized by acetylacetone and Betti base, which being enol form.In the chapter four, research on Betti Base and their derivatives with glutaraldehyde or o-phthaldialdehyde in the presence of NaCN, and we obtained Betti base derivatives of 14 and 17 by condensation reaction which were in 78-89% yield.更多还原