Studies On Synthesis And Application In Chiral Recognition Of The Two Chiral Compounds

::Chiral carboxylic acid is vital structural unit of the natural product and chiral drugs, the enantiomers of the chiral have different biological activity in the clinical. So it is very important to make the chiral recognition for the chiral carboxylic acids.CSCs of the NMR are used to measure the absolute configuration and the enantiomeric purity of chiral compounds such as chiral drugs,which has been widely used in chiral recognition researches,and it has many advantages such as easily operating,accurate,quickly effective and so on. There are many reports about chiral solvating agents. Compounds which have two chiral factors such as planar chiral and center chiral factors are widely used in catalytic asymmetric synthesis fields as chiral ligands,but there are few reports about these compounds in recognizing chiral carboxylic acids such as ibuprofen racemic compounds.So it’s important to design and compose these compounds include two chiral factors. Contents of this thesis is as following:1.The compound4-formyl-[2.2]paracyclophane can get through formylation of the reactant [2.2]paracyclophane, then with the R-α phenethylamine through the condensation dehydration、resolution and reducton reaction to obtain a kind of new two chiral compound [N-(1-phenylethyl)-4-[2.2]-p-cyclophanyl]methylamine combing the planar chiral and center chiral factors; The derivatives of L-leucine bidentate chiral amino alcohols with the resoluted (R)-4-formyl-[2.2]paracyclophane through reaction of the condensation and reduction then get another kind of new two chiral compound named (Rp,S)-1,1-diphenyl-2-{[2.2]paracyclophane-methylamino}-4-methyl-pentanol; The products were characterized by IR、1HNMR and MS spectroscopy.2.The way of NMR technology was empolyed to investigated the enantioselective ability of the two chiral compounds as the host molecules CSA to recognize the chiral drugs ibuprofen and other carboxylic acids compounds which was chosen as guests.The results showed that when it was the same ratio to mix after testing, both the two hosts showed better chiral recognition effect. Compare the ability of the two host’s chiral recognition ability, the second chiral compound (Rp,S)-1,1-diphenyl-2-{[2.2]paracyclophane-methylamino}-4-methyl-pe-ntanol exhibited best enantioselective chiral recognition ability.3. On the basis of the previous work to attempt to do some things about synthesis the chiral macrocyclic compounds, let the compound4-formyl-[2.2]paracyclophane as the reactant, through oxidation and ortho formylation reaction got the chiral macrocyclic reagent4-formyl-5-hydroxy-[2.2]paracyclophane(FHPC).;2,6-pyridinedicarbox-ylic acid through methylation、reduction and nucleophilic reaction get another reagent2,6-2-pyridine bromide generation; The two reagents rhrough condensation then with the diamine compounds (R, R)-1,2(-)-hexamethylene diamine or (R)-(-)-1,1-Bi(2-naphth-ylamine) through condensation and KBH4reduction to try to obtain the finaly the target products two kind of chiral macrocyclic compounds.