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1、1，3-环己二酮的合成工艺研究第2O卷第6期2006年l2月高校化学工程JournalofChemicalEngineeringofChineseUniversitiesNo.6Vb1.2ODeC.2006文章编号:1003-9015(2006)06—0974—04(15一【2一(乙硫基)丙基卜1,3一环己二酮的合成工艺研究戴立言,方俊',姜昕鹏',石永根,陈英奇,吕秀阳浙本学化学工程与生物工程学系制药工程研究所,浙江杭州310027;糖2.浙江上虞三和医药化工有限公司,浙江上3l2369)摘要:研究优化了合成烯草酮,烯禾定以及cloproxydim等环己烯酮类除草剂
2、的重要中间体5一【2一(乙硫基)丙基】-l,3一环己二酮的合成方法.首先,巴豆醛与乙硫醇在三乙胺中高收率制得3-乙硫基丁醛,然后以乙酰乙酸甲酯为原料,通过碱水解,与3一乙硫基丁醛缩和,脱水三步反应合成6一乙硫基庚烷-3-烯-2-酮,接着6.乙硫基庚烷.3.烯.2.酮与丙二酸二甲酯经Michael~D成和Claisen缩合,再通过皂化和脱羧反应生成目标化合物5一【2一(乙硫基)丙基】.1,3.环己二酮,主要中间产物以及目标产品均与标准品对照,经液质联用确认.关键词:5一【2.(乙硫基)丙基】.1,3.环己二酮;环己烯酮类除草剂:中间体;合成中图分类号:0643.321文
3、献标识码:ASynthesisof5-【2-(cthylthio)propy1]一1,3-eyelohexanedioneDAILi-yan,FANGJun,JIANGXin—peng,SHIYong—gen2,CHENYing-qi,Lr3Xiu.yang(1.InstituteofPharmaceuticalEngineering,DepartmentofChemicalandBiochemicalEngineering,ZhejiangUniversity,Hangzhou310027,China;2.ShangyuSanhePharmaceuticalsChe
4、micalEngineeringCo.Ltd.ofZhejiang,Shangyu312369,China)Abstract:5一【2一(ethylthio)propy1]一1,3-cyclohexanedione,thetitlecompoundofthisstudy,isanimportantintermediateforpreparationof3-hydroxy—cyclohex-2-enonesherbicides,suchasclethodim,sethoxydim,cloproxydim,etc..Theoptimizationofthesynthesi
5、srouteandthepreparationmethodofthetitlecompoundwerestudiedandtheresultsweredescribedconciselyasfollows.Firstly,3-ethylthiobutanalWaSpreparedwithhighyieldbyreactingcrotonaldehydewithethanethiolintriethylarnine.Secondly,methylacetoacetatewasconvertedto6-ethylthiohept一3一en-2-oneviathreeste
6、ps,hydrolysis,condensationwith3-ethylthiobutanalanddehydration,thenthe6-ethylthiohept一3一en一2一oneWaScyclocondensedwithdi-MemalonatebyMichaeladditionandClasisencondensation,andfurtherviasaponificationanddecarboxylation,thetitlecompoundWasobtained.Theproductsofeachstepsandthefinaltitlecomp
7、oundobtainedwerecomparedwitheachitsownstanderdsamplesandwereconfirmedbyLC/MS.Keywords:5一[2-(ethylthio)propy1]一1,3一cyclohexanedione;cyclohex-2一enonesherbicides;intermediate;synthesisl前言5一【2一(乙硫基)丙基】-1,3一环己二酮(I)是环己烯酮类除草剂烯草酮(clethodim),烯禾定(sethoxydim),以及cloproxydim等的重要中间体,该类除草剂是AC
