Synthesis method of full antitype long chain terebanthenes primary alcohol

Abstract

A synthetic method of the all trans long chain terpene primary alcohol is provided, which belongs to the technology field of the organic synthesis. The invention uses the cheap and easily gained geraniol, 2-allylic alcohol or the long chain terpene primary alcohol synthesized by the method as initial materials and uses the ethylenic chlorination reaction happened between the terpene primary alcohol acetate and the lime chlorite to form double bonds and the coupling reaction between the benzene sulphinate ester and the allyl chloride under alkali condition as the key steps, and gain the products through the hydrolysis reaction of the benzene removal sulphinate group and ester of the coupling product. The invention fully utilizes the complete framework of the primary alcohol and adds one or a plurality of isopentene units via coupling and synthesizes series of long chain terpene primary alcohol, which fully embodies the synthesis conception of the atomic economy; only a novel double bonds is formed in the reaction and other double bonds are the all trans double bonds in the raw materials, thereby ensures the trans configuration of the double bonds in the generated long chain terpene primary alcohol to the greatest extent. The invention has moderate reaction condition, simple synthetic route, simple operation, good reaction selectivity, high productive rate, easy separation and purification of the products and small environmental pollution.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Background technique [0002] Long-chain terpene primary alcohols are long-chain alcohols with multiple isopentenyl units. Primary terpene alcohols in nature mainly include geraniol, nerol, and solanesol. Long-chain terpene primary alcohols have very important uses in synthesis, in coenzyme Q, vitamin K 2 In the synthesis of such series of compounds, all-trans long-chain terpene primary alcohols with different lengths can be used to synthesize side chains. Coenzyme Q, vitamin K 2 Such series of compounds have good physiological activities, so their synthesis has been widely concerned by people. In terms of side chain synthesis, although there are many methods, the reported methods either have long steps and low overall yield, or re-form one or more double bonds during synthesis, resulting in a large number of cis-isomers in the product, resulting in Product separation and purificat...

AI Technical Summary

Problems solved by technology

[0010] There are following deficiencies in the above-mentioned synthetic method: (1) step lengthy

It takes multiple steps to connect an isopentene unit. Every time an isopentene unit is added, a newly formed double bond will be added, and among the newly formed double bonds, the cis configuration occupies a certain proportion. Therefore, If this method is used to increase multiple isopentene units, the final long-chain terpene primary alcohol will be a mixture of various cis-trans isomerisms, and the product is difficult to separate, and it cannot be guaranteed that the product has a side chain all-trans type. Physiological activity

(2) Some reagents are expensive

(3) The reaction conditions are harsh

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