| 1,3,8-三羟基-6-甲酰基-9,10-蒽醌的合成 |
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| 引用本文： | 王兴坡,徐文方.1,3,8-三羟基-6-甲酰基-9,10-蒽醌的合成[J].精细化工,2006,23(1):38-40,53. |
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| 作者姓名： | 王兴坡 徐文方 |
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| 作者单位： | 1. 山东大学,化学与化工学院,山东,济南,250012
2. 山东大学,药学院,山东,济南,250012 |
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| 摘 要： | 以大黄素(Ⅱ)为原料,在丙酮中与硫酸二甲酯〔n(Ⅱ)∶n(硫酸二甲酯)=1∶20〕反应24 h得到1,3,8-三甲氧基-6-甲基-9,10-蒽醌(Ⅲ),收率为95%;Ⅲ在过氧化苯甲酰及光引发下与N-溴代丁二酰亚胺(NBS)〔n(Ⅲ)∶n(NBS)=1∶3.45〕在四氯化碳中反应25 h得到1,3,8-三甲氧基-6-二溴甲基-9,10-蒽醌(Ⅳ),收率为70%;Ⅳ在甲氧基乙醇中水解10 m in,经氯仿萃取得1,3,8-三甲氧基-6-甲酰基-9,10-蒽醌(Ⅴ),收率为96%;最后化合物Ⅴ在氮气保护及冰水浴条件下与三溴化硼〔n(Ⅴ)∶n(BB r3)=1∶10〕反应2 h,合成了目标化合物1,3,8-三羟基-6-甲酰基-9,10-蒽醌(Ⅰ),总收率为47.2%。
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| 关 键 词： | 1 3 8-三羟基-6-甲酰基-9 10-蒽醌 大黄素 溴代反应 BBr3 |
| 文章编号： | 1003-5214（2006）01-0038-04 |
| 收稿时间： | 2005-05-30 |
| 修稿时间： | 2005-05-302005-08-11 |
Synthesis of 1,3,8-Trihydroxy-6-formyl-9,10-anthraquinone |
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| WANG Xing-po,XU Wen-fang.Synthesis of 1,3,8-Trihydroxy-6-formyl-9,10-anthraquinone[J].Fine Chemicals,2006,23(1):38-40,53. |
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| Authors: | WANG Xing-po XU Wen-fang |
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| Affiliation: | 1.School of Chemistry and Chemical Engineering, Shandong University, Jinan 250012, Shandong, China;2. School of Pharmacy, Shandong University, Jinan 250012,Shandong, China |
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| Abstract: | Starting from emodin(1,3,8-trihydroxy-6-methyl-9,10anthraquinone,Ⅱ),1,3,8-trimethoxy-6-methyl-9,10-anthraquinone(Ⅲ) was prepared by reaction with dimethyl sulfate(n(Ⅱ)∶n(dimethyl sulfate)=1∶20) in acetone for 24 h in 95% yield.Under the initiation of benzoyl peroxide and light,Ⅲ reacted with N-bromosuccinimide(NBS)(n(Ⅲ)∶n(NBS)=1∶3.45) in CCl_4 for 25 h to give 1,3,8-trimethoxy-6-dibromomethyl-9,10-anthraquinone(Ⅳ) in 70% yield.Hydrolysis of Ⅳ in methoxyethanol for 10 min in the presence of AgNO_3 gave 1,3,8-trimethoxy-6-formyl-9,10-anthraquinone(Ⅴ) in 96% yield.Finally,under protection of N_2,Ⅴ reacted with BBr_3(n(Ⅴ)∶n(BBr_3)=1∶10)in ice bath for 2 h and the target compound(1,3,8-trihydroxy-6-formyl-9,10-anthraquinone,Ⅰ) was synthesized in total yield of 47.2%. |
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| Keywords: | BBr3 |
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