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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (05): 918-921. 上一篇    下一篇

研究简报

天然产物1,3-二-(2-羟基-4-甲氧基苯基)丙烷和1,3-二-(2,4-二羟基苯基)丙烷的合成

杨金会*,a，孟丽聪a,b   

  1. (a宁夏大学能源化工自治区重点实验室 银川 750021)
    (b唐山学院环境与化学工程系 唐山 063000)
  • 收稿日期:2007-09-22 修回日期:2007-11-03 发布日期:2008-05-20
  • 通讯作者: 杨金会

Syntheses of 1,3-Bis(2-hydroxy-4-methoxyphenyl)propane and 1,3-Bis(2,4-dihydroxyphenyl)propane

YANG Jin-Hui*,a,MENG Li-Conga,b   

  1. (a Key Laboratory of Energy Sources and Chemical Engineering of Ningxia, Ningxia University, Yinchuan 750021)
    (b Department of Environmental Science and Chemical Engineering, Tangshan College, Tangshan 063000)
  • Received:2007-09-22 Revised:2007-11-03 Published:2008-05-20
  • Contact: YANG Jin-Hui

PDF

1896

被引次数

25

1,3-二-(2-羟基-4-甲氧基苯基)丙烷(1)和1,3-二-(2,4-二羟基苯基)丙烷(2)是从菊叶薯蓣(Dioscorea composita Hemsl.)分离出来的天然产物, 以间苯二酚为起始原料, 分别经甲酰化和乙酰化得到2,4-二羟基苯甲醛和2,4-二羟基苯乙酮, 然后经选择性地甲基化、甲氧甲基化、羟醛缩合、还原、脱保护等步骤完成了上述两种天然产物的首次全合成. 产物通过1H NMR, IR, MS进行了结构确证.

关键词: 1,3-二芳基丙烷, 查尔酮, 天然产物, 合成

Two natural products 1,3-bis(2-hydroxy-4-methoxyphenyl)propane (1) and 1,3-bis(2,4-dihydr- oxyphenyl)propane (2), isolated from the dried rhizomes of Dioscorea composita Hemsl., were first synthesized by acylation, methoxymethyl protection or methylation, condensation, catalytic hydrogenation, deoxygenation and deprotection starting from resorcinol. 2,4-Dihydroxybenzaldehyde and 2,4-dihydroxyacetophenone were synthesized from resorcinol, which were followed by protection with standard methylation or methoxymethylation to afford 4-methoxy-2-methoxymethoxybenzaldehyde and 2-hydroxy-4-methoxyl- acetophenone. The desired chal-cone was obtained by condensing 4-methoxy- 2-methoxymethoxyben- zaldehyde with 2-hydroxy-4-methoxylacetophenone, which was then reducted by catalytic hydrogenation and deoxygena-tion to give the title compound 1,3-bis(2-hydroxy- 4-methoxyphenyl)propane (1). Another desired product 1,3-bis(2,4-dihydroxyphenyl)propane (2) was obtained by treatment of 1 with boron tribromide in anhydrous methylene dichloride. Their structures were confirmed by 1H NMR, IR and MS techniques.

Key words: chalcone, natural product, synthesis, 1,3-diarylpropane