期刊文献+

(S)-1-苯基-1,2-乙二醇的合成 被引量:1

Synthesis of (S)-1-phenyl-1,2-ethanediol
下载PDF
导出
摘要 The synthesis of(S)-1-phenyl-1,2-ethanediol was studied in this article.Firstly,1,2-dibromo-1-phenylethane was synthesized with styrene and bromine as starting agents.The effects of some factors,including raw materials’ molar ratio,reaction time and solvents,on the yield of 1,2-dibromo-1-phenylethane were examined.Secondly,1-phenyl-1,2-ethanediol was obtained by use of hydrolysis of 1,2-dibromo-1-phenylethane in alkaline medium.The influence of reaction time and medium on the yield of 1-phenyl-1,2-ethanediol was also examined.Under the optimized conditions,the yield of 1,2-dibromo-1-phenylethane was 90.1% while the yield of 1-phenyl-1,2-ethanediol was 78.5%.Finally,(S)-1-phenyl-1,2-ethanediol was received by deracemization of 1-phenyl-1,2-ethanediol employing Candida parapsilosis.The enantiomeric excess of(S)-1-phenyl-1,2-ethanediol was 99% and the conversion was 88%. The synthesis of(S)-1-phenyl-1,2-ethanediol was studied in this article. Firstly, 1,2-dibromo-1-phenylethane was synthesized with styrene and bromine as starting agents. The effects of some factors, including raw materials' molar ratio, reaction time and solvents, on the yield of 1 ,2-dibromo-1-phenylethane were examined. Secondly, 1-phenyl-1,2-ethanediol was obtained by use of hydrolysis of 1,2-dibromo-1 -phenylethane in alkaline medium. The influence of reaction time and medium on the yield of 1-phenyl-1, 2-ethanedlol was also examined. Under the optimized conditions, the yield of 1,2-dibromo-l-phenylethane was 90. 1% while the yield of 1-phenyl-1,2-ethanediol was 78.5%. Finally, (S) -1 -phenyl-1 ,2-ethanediol was received by deracemization of 1-phenyl-1, 2-ethanediol employing Candida parapsilosis. The enantiomeric excess of( S) -1 -phenyl-1,2-ethanediol was 99% and the conversion was 88%.
出处 《化学研究与应用》 CAS CSCD 北大核心 2009年第10期1435-1438,共4页 Chemical Research and Application
基金 国家863计划(2006AA10Z310)资助项目 华东理工大学生物反应器工程国家重点实验室开放课题资助项目
关键词 (S)-1-苯基-1 2-乙二醇 苯乙烯 1 2-二溴-1-苯基乙烷 近平滑假丝酵母 生物转化 (S) -1 -phenyl-1,2-ethanediol styrene 1,2-dibromo-1 -phenylethane candida parapsilosis biotransformation
  • 相关文献

参考文献14

  • 1Jurcek O,Wimmerova M, Wimmer Z. Selected chiral alcohols:enzymic resolution and reduction of convenient substrates [ J ]. Coordin. Chem. Rev. , 2008,252 : 767-781. 被引量:1
  • 2张文虎,蔡燕,刘湘,方云,许建和.芳香酮的不对称还原[J].化学进展,2007,19(10):1537-1552. 被引量:7
  • 3Shinobu O,Yutaka K,Yasushi N. Synthesis of optically active mandelic acid via microbial oxidation of racemie 1- phenyl-1, 2-ethanediol [J]. Biosci. Biotech. Biochem., 1992,56(8) :1216-1220. 被引量:1
  • 4Schmid A, Dordick J S, Hauer B, et al. Industrial biocatalysis today and tomorrow [J]. Nature, 2001 , 409 ( 1 ) : 258-268. 被引量:1
  • 5Liu Z Y, Michel J, Wang Z S, et al. Enantioselective hydrolysis of styrene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200 [ J ]. Tetrahedron :Asymmetry, 2006,17:47-52. 被引量:1
  • 6Rui L Y, Cao L, Chen W, et al. Protein engineering of epoxide hydrolase from agrobacterium radiobacter AD1 for enhanced activity and enantioselective production of(R)-1- phenylethane- 1,2-diol [ J ]. Applied and Environmental Microbiology ,2005,71 ( 7 ) :3995-4003. 被引量:1
  • 7Balagam B, Mitra R, Richardson D E. Osmium-catalyzed asymmetric dihydroxylation by carbon dioxide-activated hydrogen peroxide and N-methylmorpholine [ J]. Tetrahedron Letters, 2008,49 : 1071 - 1075. 被引量:1
  • 8Choi D S, Han S S, Kwueon E K, et al. New mono-quarternized bis-cinchona alkaloid ligands for asymmetric dihydroxylation of olefins in aqueous medium: unprecedented high enantioselectivity and recyclability [ J ]. Adv. Synth. Catal. ,2006,348:2560-2564. 被引量:1
  • 9Wu P, Hilgraf R, Fokin V V. Osmiun-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle. [ J ]. Adv. Synth. Catal. ,2006,348 : 1079-1085. 被引量:1
  • 10Iwasaki F,Maki T,Onomura O,et al. Chemo-and stereoselective monobenzoylation of 1,2-diols catalyzed by orga notin compounds [J]. J. Org. Chem. ,2000,65:996-1002. 被引量:1

二级参考文献126

共引文献18

同被引文献9

引证文献1

二级引证文献7

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