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1,4,5,8-四甲氧基萘-2-甲醛的合成 被引量:1

Synthesis of 1,4,5,8-Tetramethoxynaphthalene-2-carboxaldehyde
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摘要 对紫草素合成中间体1,4,5,8-四甲氧基萘-2-甲醛的制备工艺进行了改进,由萘茜在溴化四丁基铵催化下进行还原甲基化的收率由文献报道的44%提高到90%,标题化合物总收率72%(以对二甲氧基苯计)。 The synthesis of 1,4,5,8-tetramethoxynaphthalene-2-carboxaldehyde, an intermediate of shikonin wasinvestigated. The yield of the tandem reduction and methylation of 5,8-dihydroxy-1,4-naphthoquinone was increased from44% to 90% in the presence of phase transfer catalyst tetrabutylammonium bromide. The overall yield of title compoundwas 72% based on 1,4-dimethoxybenzene.
出处 《中国医药工业杂志》 CAS CSCD 北大核心 2004年第10期583-585,共3页 Chinese Journal of Pharmaceuticals
基金 上海-SK研究与发展基金(2003014-h)
关键词 1 4 5 8-四甲氧基萘-2-甲醛 紫草素 中间体 合成 tetramethoxynaphthalene-2-carboxaldehyde shikonin intermediate synthesis
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参考文献6

  • 1Papageorgiou VP, Assimopoulou AN, Couladouros EA, et al.The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products [J]. Angew Chem Int Ed, 1999,38 (3): 270-300.
  • 2Pearson MS, Jensky BJ, Greer FX, et al. Substituent effects in the Keto-Enol tautomerism of fused 1,4-naphthalenediols [J].J Org Chem, 1978, 43 (24): 4617-4621.
  • 3Lewis JR, Paul J. A convenient synthesis of naphthazarin and naphthopurpurin [J]. Z Naturforsch B: Anorg Chem Org Chem, 1977, 32B (12): 1473-1475.
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二级参考文献4

  • 1Bakola-Christianopoulou M N. European Journal of Medicinal Chemistry . 1998
  • 2Sukenik C N,Weissman B A,Bergman R G. J. Journal of the American Chemical Society . 1975
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共引文献3

同被引文献4

  • 1Papageorgiou V P,Assimopoulou A N,Couladouros E A,et al.The chemistry and biology of alkannin,shikonin,and related naphthazarin natural products[J].Angew Chem Int Ed,1999,38(3):270-300.
  • 2Terada A,Tanoue Y,Hatada A,et al.Synthesis of shikalkin[(±)-shikonin]and related compounds[J].Bull·Chem·Soc·Jpn,1987,60(1):205-213.
  • 3Pearson M S,Jensky B J,Greer F X,et al.Substituent effects in the Keto-Enoltautomerism of fused 1,4-naphthalenediols[J].J Org Chem,1978,43(24):4617-4621.
  • 4Lewis J R,Paul J.A convenient synthesis of naphthazarin and naphthopurpurin[J].Z Naturforsch B:Anorg Chem Org Chem,1977,32B(12):1473-1475.

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