文章摘要
曹海泳,刘文琴,万屏南,林艳,崔汉峰.二烯酮类化合物在构建复杂有机化合物中的应用[J].精细化工,2020,37(8):0
二烯酮类化合物在构建复杂有机化合物中的应用
Application of Dienones in the Construction of Complex Organic Compounds
投稿时间:2020-02-10  修订日期:2020-03-31
DOI:
中文关键词: 二烯酮  2, 5-环己烯酮  1, 4-戊二烯-3-酮  2, 4-戊二烯-1-酮  有机合成  复杂有机化合物
英文关键词: dienones  cyclohexa-2, 5-dienone  penta-1, 4-dien-3-ones  penta-2, 4-dien-1-ones  organic synthesis  complex organic compounds
基金项目:
作者单位E-mail
曹海泳 江西中医药大学 297770326@qq.com 
刘文琴 江西中医药大学  
万屏南 江西中医药大学  
林艳 江西中医药大学  
崔汉峰 江西中医药大学  
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中文摘要:
      二烯酮作为一类具有多个化学反应位点的不饱和酮类化合物,可与多种反应底物实现不同类型的化学转化,高效快捷地构建功能各异的有机化合物。该文综述了近些年二烯酮类化合物与多种反应底物的化学转化,首先探讨了2,5-环己烯酮类二烯酮与不同试剂的串联Michael-Smiles环丙烷化反应、环加成反应、三组分Ritter反应、光化学重排反应和氧化偶联反应分别构建了环丙烷类衍生物、含氟烷基N,O-缩酮类衍生物、稠环吲哚类化合物、酰胺类化合物和不对称的联芳烃类化合物,接着分析了1,4-戊二烯-3-酮类二烯酮与丙二腈(硝基甲烷)、硫氢化钠、氧化吲哚、吡唑酮、芴和巴比妥酸双Michael加成反应,分别合成了多取代环己酮类化合物、二芳基噻喃酮类化合物、螺环氧化吲哚类化合物、螺环吡唑酮类化合物、螺环芴类化合物和螺环巴比妥类衍生物,然后研究了2,4-戊二烯-1-酮类二烯酮的1,4-共轭加成、氮杂Michael加成反应、分子内MBH反应、分子内还原Aldol反应、分子内Aldol反应和分子内[4+2]环加成/氧化反应分别实现了有机含硫化合物、有机含氮化合物、多取代茚酮类化合物和SGLT2抑制剂——托格列净关键中间体的制备,最后对二烯酮在后续化学反应中的潜在应用进行了展望。
英文摘要:
      Dienones, a kind of unsaturated ketones with multiple chemical reaction sites, can achieve different types of chemical conversion with a variety of substrates, and construct organic compounds with different functions efficiently. In this paper, the chemical transformation of dienones with different substrates in recent years was reviewed. Firstly, the series of tandem Michael-Smiles cyclopropanation reaction, cycloaddition reaction, three-component Ritter reaction, photoinduced rearrangement reaction and direct oxidative coupling reaction of cyclohexa-2,5-dienone with different reagents were studied. The cyclopropane derivatives, fluoroalkylated N,O-ketal derivatives, ring-fused indoles, amides and unsymmetrical biaryls were constructed respectively. Secondly, the double Michael addition of penta-1,4-dien-3-ones with malononitrile, nitromethane, sodium hydrosulfide, oxindole, pyrazolone, fluorene and barbituric acid were analyzed, and the multi-substituted cyclohexanones, diaryltetrahydrothiopyran-4-ones, spirocyclic oxindoles, spirocyclic pyrazolones, spirofluorenes and spirobarbituric acid derivatives were synthesized. Then, we studied the 1, 4-conjugate addition, Aza-Michael addition, intramolecular Morita–Baylis–Hillman (IMBH) reaction, intramolecular reductive Aldol reaction, intramolecular Aldol reaction and intramolecular [4+2] cycloaddition reaction of penta-2,4-dien-1-ones realizing the preparation of organic sulfur compounds, organic nitrogen compounds, multi-substituted indanones and key intermediate of Tofogliflozin. Finally, the potential application of dienones in the subsequent chemical reactions was prospected.
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