李术艳,沈淑君.2-烯-1,4-二酮及其衍生物的合成及晶体结构[J].井冈山大学自然版,2017,(2):35-39 |
2-烯-1,4-二酮及其衍生物的合成及晶体结构 |
SYNTHESIS AND CRYSTAL STRUCTURE OF 1, 4-ENEDIONE AND ITS DERIVATIVES |
投稿时间:2016-11-04 修订日期:2016-12-30 |
DOI:10.3969/j.issn.1674-8085.2017.02.008 |
中文关键词: 2-烯-1,4-二酮 1,3-二酮 建筑模块 X-单晶衍射 |
英文关键词: 1,4-enedione 1,3-dione building block single crystal X-ray diffraction |
基金项目:福建省教育厅科技计划项目(JA13388);漳州职业技术学院科研项目(ZZY1308) |
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中文摘要: |
通过对三取代-2-烯-1,4-二酮及其衍生物进行了探索合成。在环戊二烯基三苯基膦氯化镍[C5H6(PPh3)NiCl]作用下,由N-甲基-N-苯(/4-甲基苯基)甲酰基亚甲基苯胺与1,3 -二苯基-1,3-丙二酮在二氯乙烷(DCE)介质中发生Knoevenagel交叉偶联反应,得到α位具有三个羰基的乙烯化合物,即三取代2-烯-1,4-二酮。同时,对上述产物与胺类亲核试剂进行了自动串联催化反应的探索合成,并摸索条件进行优化。通过核磁共振氢谱、核磁共振碳谱及X-单晶衍射等手段对合成产物的结构进行了表征,证明了合成方法的可靠性。 |
英文摘要: |
The 1,4-enedione scaffold, which exists in natural products and pharmaceutical compounds, has broad applications in organic synthesis as a versatile building block. Therefore, this study explored the method to synthesize the trisubstituted 1,4-enedione and its derivatives. Chlorocyclopentadieny (triphenylphosphine) nickel promoted the reaction of N-methyl-N-phenyl-acetophenone (or N-methyl-N-(4-methyl)phenylacetophenone) with 1,3-diphenylpropane-1,3-di-one in dichloroethane, providing a convenient route to the synthesis of ethylene compound 1,4-enedione with three carbonyl groups in the position of α. It developed as Knoevenagel cross-coupling reaction. In addition, the above products were used to react with amine nucleophiles through automatic tandem catalytic reaction and the conditions were optimized. All compounds were characterized by IR, 1HNMR, 13CNMR and single X-ray crystal diffraction analysis, which proved the reliability of the method. |
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