| 5-甲基-3-硝甲基己酸乙酯的合成 |
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| 引用本文： | 肖林久,杜彩芹,姜新东,姚兴旺,张心心. 5-甲基-3-硝甲基己酸乙酯的合成[J]. 合成化学, 2017, 25(11): 953-956. DOI: 10.15952/j.cnki.cjsc.1005-1511.2017.11.17088 |
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| 作者姓名： | 肖林久 杜彩芹 姜新东 姚兴旺 张心心 |
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| 作者单位： | 1. 沈阳化工大学 a. 应用化学学院， b. 辽宁省稀土化学及应用重点实验室，辽宁 沈阳 110142 |
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| 基金项目： | 辽宁省科技计划科技攻关项目 |
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| 摘 要： | 以异戊醛和膦酰乙酸三乙酯为原料，1,8-二氮杂二环［5,4,0］十一碳-7-烯(DBU)为催化剂，碘化钠为磷酸酯碳负离子稳定助剂，经Horner-Wadsworth Emmons反应合成了5-甲基-2-己烯酸乙酯(3)，收率90%;仍以DBU为催化剂，3与硝基甲烷经Michael加成反应合成5-甲基-3-硝甲基己酸乙酯，收率98%，两步总收率88.2%，其结构经1H NMR和IR确证。
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| 关 键 词： | 异戊醛 膦酰乙酸三乙酯 5-甲基-3-硝甲基己酸乙酯 5-甲基-2-己烯酸乙酯 1 8-二氮杂二环 ［5 4 0］十一碳-7-烯 Horner-Wadsworth-Emmons反应 Michael加成反应 药物合成 |
| 收稿时间： | 2017-04-16 |
Synthesis of Ethyl 5-Methyl-3-nitromethyl Hexanoate |
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| XIAO Lin-jiu,DU Cai-qin,JIANG Xin-dong,YAO Xing-wang,ZHANG Xin-xin. Synthesis of Ethyl 5-Methyl-3-nitromethyl Hexanoate[J]. Chinese Journal of Synthetic Chemistry, 2017, 25(11): 953-956. DOI: 10.15952/j.cnki.cjsc.1005-1511.2017.11.17088 |
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| Authors: | XIAO Lin-jiu DU Cai-qin JIANG Xin-dong YAO Xing-wang ZHANG Xin-xin |
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| Affiliation: | a. College of Applied Chemistry; b. Liaoning Provincial Key Laboratory of Rare Earth Chemistry and Application, 1. Shenyang University of Chemical Technology, Shenyang 110142, China |
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| Abstract: | Ethyl 5-methylhex-2-enoate(3) with the yield of 90%was prepared by Horner-Wadsworth-Emmons reaction of isovaleraldehyde with triethylphosphonoacetate using 1,8-diazabicyclo[5.4.0]un-dec-7-ene(DBU) as the catalyst, NaI as phosphate ester anion stabilizer .3 reacted with nitromethane by Michael addition reaction to obtain ethyl 3-( nitromethyl )-5-methylhexanoate , using DBU as cata-lyst, the yield was 98%.The overall yield reached 88.2%.The structure was confirmed by 1 H NMR and IR. |
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| Keywords: | isovaleraldehyde triethylphosphonoacetate ethyl 3-( nitromethyl )-5-methylhexanoate ethyl 5-methylhex-2-enoate 1,8-diazabicyclo[5.4.0]undec-7-ene Horner-Wadsworth-Emmons reac-tion Michael addition drug synthesis |
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