增感剂DPO的合成工艺研究

Study on synthesis process for a new photosensitizer-DPO

以苯亚磺酸钠和氯乙酸乙酯为起始原料,首先合成苯砜乙酸乙酯(Ⅰ);再与由1,1,3,3-四甲氧基丙烷与二乙胺反应得到的N,N-双乙基胺-1,3-二丙烯醋酸盐反应,得5-二乙基氨基-2-苯磺酰基-2,4-戊二烯乙酸乙酯(Ⅱ)中间体;最后与正辛醇酯交换得到目标产物5-二乙基氨基-2-苯磺酰基-2,4-戊二烯乙酸辛酯(DPO)。考察了溶剂的种类对制备化合物Ⅰ和投料比、反应温度对制备化合物Ⅱ的影响,并且通过重结晶法纯化DPO产品,最终可使产品DPO收率达到69.58%、产品纯度大于99.50%,并通过LC-MS和1H NMR对产品及中间产品进行了结构分析与确证。

Ethyl phenylsulfonyl acetate（ I ）was prepared by sodium benzenesulfinate and ethyl chloroacetate, then reacted with 1,3- bis-diethylaminotrimethinium diatate which was prepared by 1,1,3,3-tetramethoxypropane and diethylamine to get 5-（ diethylami- no） -2-（phenylsulfonyl） -2,4-pentadienoie acid ethyl ester（ II ） ,finally the target product 5-（diethylamino） -2-（phenylsulfonyl） -2, 4-pentadienoic acid octyl ester（DPO） was obtained after ester exchange reaction with octanol. Influences of different solvents on the preparation of compound I and the reactant ratio, temperature on the preparation of compounds II were studied. The DPO was puri- fied by reerystsllization. Results indicated that the yield of DPO was 69.58% with the purity which was higher than 99.50%. The intermediated and target products were all confirms by LC-MS and 1H-NMR.