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两种3,5-二氨基苯甲酰氨基脂肪酸盐酸盐的合成

Synthesis of Two 3,5-Diaminobenzoylamido Fatty Acid Hydrochlorides

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【作者】 于世钧廖春泉聂鑫李红李士锋

【Author】 YU Shi-jun,LIAO Chun-quan,NIE Xin,LI Hong,LI Shi-feng(School of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian 116029,Liaoning,China)

【机构】 辽宁师范大学化学化工学院辽宁师范大学化学化工学院 辽宁大连116029辽宁大连116029

【摘要】 以3,5-二硝基苯甲酰氯、3-氨基丙酸和6-氨基正己酸为原料,室温反应合成了3-(3,5-二硝基苯甲酰氨基)丙酸和6-(3,5-二硝基苯甲酰氨基)正己酸。反应过程中,3,5-二硝基苯甲酰氯分批加入,滴加2 mol/L氢氧化钠水溶液控制反应体系的pH=8~9,n(3,5-二硝基苯甲酰氯)/n(氨基酸)=1,收率分别为84%和81%;硝基化合物经10%钯炭催化剂(用量为反应物质量的10%)催化加氢,再经盐酸酸化,得目标产物3-(3,5-二氨基苯甲酰氨基)丙酸盐酸盐和6-(3,5-二氨基苯甲酰氨基)正己酸盐酸盐,收率分别为93%和94%。相关化合物的结构通过FTIR1、HNMR1、3CNMR进行了表征。

【Abstract】 3-(3,5-Dinitrobenzoylamido)propanoic acid(Ⅰ) and 6-(3,5-dinitrobenzoylamido) hexanoic acid(Ⅱ) were synthesized respectively by reaction of 3,5-dinitrobenzoyl chloride with 3-aminopropanoic acid and 6-aminohexanoic acid at room temperature.In the experiment,3,5-dinitrobenzoyl chloride should be added in portions,2 mol/L aqueous NaOH solution was dropped into the reaction system to keep pH=8~9,and n(3,5-dinitrobenzoyl chloride)∶n(amino acid)=1.Yields of Ⅰ and Ⅱ are 84% and 81% respectively.The nitro compounds Ⅰ and Ⅱ were hydrogenated with 10%Pd /C as catalyst(m(catalyst)∶m(nitro compound)=10∶100),and then acidized with hydrochloric acid to get the title compounds 3-(3,5-diaminobenzoylamido)propanoic acid hydrochloride and 6-(3,5-diaminobenzoylamido)hexanoic acid hydrochloride in 93% and 94% yield respectively.Structures of the compounds were confirmed by FTIR,1HNMR and 13CNMR.

【基金】 国家自然科学基金资助项目(20573049)~~
  • 【分类号】TQ246
  • 【下载频次】129
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