Synthesis Of Gentisyl Alcohol-type Marine Natural Products And Its Application

Gentisyl alcohol is isolated from the sponge in the extraction of marine natural products.It not only has antibacterial,antioxidant,free radical elimination,anti-biological attachment and other biological activity,but also can be used as sphingomyelinase inhibitors.In this thesis,five kinds of marine natural products of gentisyl alcohol,chlorogentisyl alcohol,gentisyl quinone,chlorogentisyl quinone and toluhydroquinone were synthesized by the synthesis of chlorotolylol compounds.gentisyl quinone and chlorogentisyl quinone are the first synthesis.Then 2,5-dimethoxybenzaldehyde grafted successfully to natural polymer chitosan,prepared chitosan zwitterionic polymer functional materials.The main research work is divided into the following parts:1.Methodological study on the synthesis of gentisyl alcohol-type marine natural products.The regional selectivity of the chlorination reaction is a key step in the synthesis of gentisyl quinone and chlorogentisyl quinone.The halogenation reaction was studied by using 2,5-dimethoxy as template,and the experimen tal results were obtained by the contradiction between the classical methoxy and aldehyde groups.The results were as follows: The hydroxyl group of the ortho position,the final aldehyde group and the meta-position of the methoxy together from the role of the halogenation reaction occurs in the aldehyde side of the ortho.In addition,the aldehyde group alignment reaction product was monocrystalline,and its structure was confirmed by X-ray.2.Study on Synthesis of gentisyl alcohol-type marine natural products.The synthesis of chlorogentisyl alcohol mainly comprises the following steps: 2-chloro-4-methoxyphenol was prepared by chlorination reaction with 4-methoxyphenol as raw material,2-Chloro-6-hydroxymethyl-4-methoxyphenol was prepared by the methylation of phenol with 2-chloro-4-methoxyphenol as raw material.2-chloro-6-hydroxymethyl-4-methoxyphenol was oxidized to achieve the first synthesis of chlorogentisyl quinone;Gentisyl alcohol was prepared by the reduction reaction of chlorogentisyl quinone.Five kinds of marine natural products of gentisyl alcohol,chlorogentisyl alcohol,gentisyl quinone,chlorogentisyl quinone and toluhydroquinone were synthesized by Using the same or similar ideas and the same raw materials.3.Study on applaction of the synthesis of gentisyl alcohol-type marine natural products.The effects of 2,5-dimethoxybenzaldehyde and chitosan on the preparation of Schiff base chitosan were studied.The Schiff base chitosan was prepared by reduction agent reduction.Under the alkaline condition,the alkylated chitosan and methyl iodide reacted to prepare chitosan zwitterionic macromolecule functional materials The prepared polymer functional materials were characterized by IR,XRD and thermogravimetric analysis,which showed that 2,5-dimethoxybenzaldehyde was successfully grafted into chitosan.In this thesis,the synthesis of a series of gentisyl alcohol-type marine natural products,such as gentisyl alcohol,chlorogentisyl alcohol,gentisyl quinone,chlorogentisyl quinone and toluhydroquinone,and grafted chitosan to prepare polygonal amphoteric macromolecule functional materials.