期刊文献+
任意字段
题名或关键词
题名
关键词
文摘
作者
第一作者
机构
刊名
分类号
参考文献
作者简介
基金资助
栏目信息

多氧取代1-环己烯甲醇的合成 被引量：3

Novel method for synthesis of polyoxygenated 1-cyclohexene-1yl-methanol
下载PDF
导出
摘要 以莽草酸为原料,与甲醇成酯,然后丙酮叉保护顺式的邻二羟基,叔丁基二甲硅氯保护另一个羟基,最后用氢化铝锂和三氯化铝还原,得到标题化合物,其结构经IR1、HNMR、HR-MS确证,总产率86.5%。对还原反应的条件进行了探索,其收率高达95.2%。 A novel method was developed and carefully studied for the synthesis of polyoxygenated cyclohexene-yl-methanol from shikimic acid by means of esterification with methanol, followed by protection by DMP and TBDMSC1 and reduction by mixed THF solution of lithium aluminum hydride and aluminum chloride. The structure of the final product was identified by ^1H NMR, IR and MS methods, and the total product yield could reach 86.5 %. Under optimized condition the yield of product obtained via the improved reduction step could reach 95.2%.
作者 李振卿 许琼明 敖桂珍 袁志军
机构地区 苏州大学药学院
出处 《化学试剂》 CAS CSCD 北大核心 2009年第6期469-470,472,共3页 Chemical Reagents
关键词 多氧取代1-环己烯甲醇 Α Β-不饱和酯 氢化铝锂 三氯化铝 还原 polyoxygenated cyclohexene-yl-methanol α,β-unsaturated ester lithium aluminum hydride aluminum chloride reduction
分类号 O623.412 [理学—有机化学]
  • 相关文献

参考文献5

  • 1LIU An,LIU Zhan-zhu,ZOU Zhong-mei,et al.Synthesis of (+)-zeylenone from shikimic acid[J].Tetrahedron,2004,60(16):3 689-3 694.
  • 2NICOLAOU K C,FREDERICK M O,BURTOLOSO A C B,et al.Chemical synthesis of the ring system of maitotoxin[J].J.Am.Chem.Soc,2008,130(25):7 816-7 817.
  • 3HAGER D C,BENTRUDE W G.Triplet-sensitized photo rearrangements of six-member-ring 2-phenylallyl phosphites.Reaction efficiency and stereochemistry at phosphorus[J].J.Org.Chem.,2000,65(9):2 786-2 791.
  • 4IKEDA T,YUE S,HUTCHINSON C R.Reductive,radical-induced cyclization of 5-hexenals as a biomimetic model of the chemistry of secologanin formation[J].J.Org.Chem.,1985,50(25):5 193-5 199.
  • 5李洋,王峰,曹小平.氢化铝锂还原α,β-不饱和羰基化合物的新反应——一种合成1,3-二醇的简便方法[J].化学学报,2003,61(2):279-284. 被引量：3

二级参考文献22

  • 1Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem.1983, 48, 4634.
  • 2Boaz, N. W. J. Org. Chem. 1992, 57, 4289.
  • 3Houghton, R. P.; Voyle, M. J. Chem. Soc., Perkin Trans. 11984, 925.
  • 4Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
  • 5Cohen, T.; Jeong, I.-H.; Mudryk, B.; Bhupathy, M.; Awad,M. M. A. J. Org. Chem. 1990, 55, 1528.
  • 6(a)Todesco, R.; Bockstaele, D. V.; Gelan, J.; Martens, H.;Put, J. J. Org. Chem. 1983, 48, 4963.(b)Barluenga, J.; Flórez, J.; Yus, M. J. Chem. Soc.,Perkin Trans. 1 1983, 3019.
  • 7(a)Snyder, E. I. J. Org. Chem. 1967, 32, 3531.(b)Popovici-Müller, J. V.; Spencer, T. A. Tetrahedron Lett.1997, 38, 8161.
  • 8Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J.Am. Chem. Soc. 1991, 113, 4252.
  • 9Balagurusamy, V. S. K.; Ungar, G.; Percec, V.;Johansson, G. J. Am. Chem. Soc. 1997, 119, 1539.
  • 10(b)Barluenga, J.; Flórez, J.; Yus, M. J. Chem. Soc.,Perkin Trans. 1 1983, 3019.

共引文献2

同被引文献16

  • 1Liao Y H, Xu L Z, Yang S L, et al. Three cyclohexeneoxides from Uvaria grandi flora [ J ]. Phytochemistry, 1997,45(4) : 7292-7321.
  • 2Xu Q M, Xu L Z, Yang S L. New polyoxygenated cyclohexenes from Uvaria kweichowensis and their antitumor activities [J]. Chem Pharm Bull, 2005, 53 (7) : 8262-8291.
  • 3Liu A, Liu Z Z, Zou Z M, et al. Synthesis of (+)- zeylenone from shikimic acid[J]. Tetrahedron, 2004,60 (16) :3689-3694.
  • 4Xu Q M, Xu L Z, Yang S L. New polyoxygenated cyclohexenes from Uvaria kweiehowensis and their antitu- mot activities [ J ]. Chem Pharm Bull, 2005,53 ( 7 ) : 8262 - 8291.
  • 5Liao Y H, Xu L Z, Yang S L, et al. Three cyclohex- ene oxides from Uvaria grandiflora [ J ]. Phytochem, 1998,45(4) :729 -732.
  • 6Arthurs C L, Wind N S, Whitehead R C, et al. Ana- logues of 2-cmtonyloxymethyl- (4R, 5R, 6R) -4,5,6-trihydroxy-cyclohex-2-enone ( COTC ) with anti - tumor properties[ J]. Bioorg & Med Chemistry Lett,2007,17:553 -557.
  • 7Arthurs C L, Raftery J, Whitby H L, et al. Useful precursors for the preparation of analogues of the anti- tumor agent, 2-crotonyloxymethyl- ( 4R, 5R, 6R ) -4,5, 6-trihydroxy-cyclohex-2-enone (COTC)[ J ]. Bioorg. & Med Chemistry Lett,2007,17:5974 - 5977.
  • 8Liu A, Liu Z Z, Zou Z M, et al. Synthesis of ( + )- zeylenone from shikimic acid [ J ]. Tetrahedron, 2004, 60(16) :3689 -3694.
  • 9Xu Q M, Xu L Z, Yang S L. Chem Pharm Bull[J]. 2005, 53 (7) : 8262-8291.
  • 10Arthurs C I., Morris G A, Piacenti M, et al. Tetrahedron[J], 2010,66: 9049-9060.

引证文献3

二级引证文献2

化学试剂
2009年 第6期

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部