CN201010211446
CN101891618A
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摘要:2-[(2,3,4-三烷氧基-6-酰基)苯基]乙酸酯及其制备方法与应用,涉及一种有机小分子化合物。以2,3,4-三烷氧基苯甲醛1为原料,用Meldrum酸转化为3-(2,3,4-三烷氧基)苯基丙酸2;在多聚磷酸作用下,2经分子内酰化得到相应的氢化茚酮3;3与Grignard试剂加成,再用酸脱水成为氢化茚4;用四氧化锇处理4得到二羟基氢化茚5;5分别用高碘酸钠和亚氯酸钠氧化得到2-[(2,3,4-三烷氧基-6-酰基)苯基]乙酸7;最后在氯化亚砜存在下,7与无水醇反应得到目标产物2-[(2,3,4-三烷氧基-6-酰基)苯基]乙酸酯8。可激活腺苷酸活化蛋白激酶,可用于制备抗糖尿病药物。
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Abstract: The invention discloses 2-[(2,3,4-trialkoxy-6-acyl) phenyl] acetic ester as well as a preparation method and application thereof and relates to an organic micromolecule compound. The preparation method comprises the following steps of: converting 2,3,4-trialkoxy benzaldehyde 1 used as a raw material into 3-(2,3,4-trialkoxy) phenylpropionic acid 2 by using Meldrum acid; under the action of polyphosphoric acid, carrying out intramolecular acylation on the 3-(2,3,4-trialkoxy) phenylpropionic acid 2 to obtain corresponding idenone hydride 3; carrying out an addition reaction on the idenone hydride 3 with a Grignard reagent and dewatering into indene hydride 4 by using acid; treating the indene hydride 4 by using osmium tetroxide to obtain dihydroxyl indene hydride 5; oxidizing the dihydroxyl indene hydride 5 respectively by using sodium periodate and sodium chlorite to obtain 2-[(2,3,4-trialkoxy-6-acyl) phenyl] acetic acid 7; and finally, reacting the 2-[(2,3,4-trialkoxy-6-acyl) phenyl] acetic acid 7 with anhydrous alcohol to obtain the 2-[(2,3,4-trialkoxy-6-acyl) phenyl] acetic ester 8 as the target product in the presence of thionyl chloride. The 2-[(2,3,4-trialkoxy-6-acyl) phenyl] acetic ester can activate monophosphate activated protein kinase and is useful for preparing anti-diabetic medicaments.
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申请人: 厦门大学
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Applicant: UNIV XIAMEN
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地址: 361005 福建省厦门市思明南********(隐藏)
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发明(设计)人: 吴乔 黄培强 张洪奎 郑忠辉 林圣彩 占艳艳 庄佳佳 陈航姿 沈月毛
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Inventor: QIAO WU; PEIQIANG HUANG; HONGKUI ZHANG; ZHONGHUI ZHENG; SHENGCAI LIN; YANYAN ZHAN; JIAJIA ZHUANG; HANGZI CHEN; YUEMAO SHEN
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主分类号: C07C69/738(2006.01)I
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分类号: C07C69/738(2006.01)I C07C67/08(2006.01)I A61K31/216(2006.01)I A61P3/10(2006.01)I
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