期刊文献+

化学-酶法耦合制备拆分β-萘乙醇

The chemical-enzymatic preparation and resolution of β-naphthyl alcohol
下载PDF
导出
摘要 通过化学-酶相耦合的方法,成功制备出e.e.值>99%的S-β-萘乙醇,使其光学纯度达到了制备R-2-萘乙胺的要求。研究中以β-萘乙酮为原料,经硼氢化钠还原得到外消旋的β-萘乙醇。经过酶催化动力学拆分,β-萘乙醇中R型底物100%全转化为酯,S构型底物型被保留,这样体系中S构型底物的e.e.值达到近100%。本文还考察了若干因素对酶催化动力学拆分过程的影响,并最终确定了酶催化动力学拆分β-萘乙醇制备S-β-萘乙醇的最适条件:反应温度45℃,溶液为甲苯,底物浓度为100 mmol/L。 A preparation method of high purity S-β-naphthyl alcohol with chemical-enzymatic process was reported.S-β-naphthyl alcohol was obtained with the kinetic resolution of rac-β-naphthyl alcohol(hydrogenized from β-naphthyl ketone),with an e.e.value near 100%.Several influence factors on the enzymatic resolution process were studied,and the optimized operation arguments were determined.
出处 《化工进展》 EI CAS CSCD 北大核心 2011年第12期2704-2707,共4页 Chemical Industry and Engineering Progress
关键词 S-β-萘乙醇 化学-酶法 β-萘乙酮 动力学拆分 S-β-naphthyl alcohol chemistry-enzyme coupling method β-naphthyl ketone kinetic resolution
  • 相关文献

参考文献11

  • 1胡键,董菁,施小新.用循环拆分法制备手性萘乙胺[J].合成化学,2010,18(1):61-63. 被引量:4
  • 2Ernesto Occhiato,Bryan Jones J.Probing enzyme stereospecificity.Inhibition ofα-chymotrypsin and subtilisin Carlsberg by chiral amine-and aminoalcohol-derivatives. Tetrahedron . 1996
  • 3Pimplaskar Harish K,Lebedev Mikhail.Crystalline salt forms of antifolate compounds and methods of manufacturing thereof. US,2009253719 . 2009
  • 4Andrei N Parvulescu,Erik Van der Eycken,Pierre A Jacobs,et al.Microwave-promoted racemization and dynamic kinetic resolution of chiral amines over Pd on alkaline earth supports and lipases. Journal of Catalysis . 2008
  • 5Yang Te Fang,Chih Hsiang.Selective reaction of camphor-derived exo-formyl[2.2.1]bicyclic carbinol with alkyl primary amines:Application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones. Tetrahedron . 2010
  • 6Kuang Yongqing,Jiang Ru.A novel planar chiral N-heterocyclic carbene–oxazoline ligand for the asymmetric hydrosilylation of ketones. Catalysis Communications . 2009
  • 7Crittall Matthew R,Rzepa Henry S,Carbery David R.Design,synthesis,and evaluation of a helicenoidal dmap lewis base catalyst. Organic Letters . 2011
  • 8LEE J H,,HAN K,KIM M J,et al.Chemoenzymatic dynamic kinetic resolution of alcohols and amines. Eur J OrgChem . 2010
  • 9Guel, N,Nelson, J.Synthesis and structure of chiral halo[N,N-dimethyl-a-(2-naphthyl)ethylamine-3, C, N] mercury(Ⅱ) complex. Journal of Molecular Structure . 1999
  • 10Mereyala H B,Pola P.Resolution of 1-arylethylamines with 5-(1,2-o-isopropylidene-3,6-anhydro-2-D-glucofuranosyl) hydrogen phthalate. Tetrahedron Asymmetry . 2003

二级参考文献8

  • 1Sheldon R A. Chirotechnology, Industrial Synthesis of Optically Active Compounds [M]. Marcel Dekker: New York, 1993.
  • 2Ski X X, Ni F, Shang H X, et al. Racemization of (S)-(+)-10,11-dimethoxyaporphine and (S)-(+)- aporpkine: Efficient preparations of (R) -( - ) -apomorphine and (R)-(-)-aporphine via a recycle process of resolution [J]. Tetrahedron : Asymmetry, 2006,17 : 2210 - 2215.
  • 3Thiel O R, Bernard C, Tormos W, et al. Practical synthesis of the calcimimetic agent, clnacalcet [J]. Tetrahedron Letters ,2008,49 : 13 - 15.
  • 4Yamada H, Kawate T, Nishida A, et al. Asymmetric addition of alkyllithium to chiral Imines : 1-Naphthylethyl group as a chiral auxiliary [J]. Journal of Organic Chemistry, 1999,64:8821 - 8828.
  • 5Pallavicini M, Valoti E, Villa L, et al. Isopropylldene glycerol hydrogen phthalate:A new resolving agent. Application to the resolution of 1-arylethylamines[J]. Tetrahedron :Asymmetry, 1996,7:1117 - 1122.
  • 6Pallavicini M, Bolchi C, Furnagalli L, et al. Highly efficient resolutions with isopropylidene glycerol 3- carboxy-2-naphthoate [J]. Tetrahedron: Asymmetry, 2002,13:2277 - 2282.
  • 7Mereyala H B, Pola P. Resolution of 1-arylethyhunines with 5-( 1, 2-O-isopropylidene-3, 6-anhydro-D-glucofuranosyl) hydrogen phthalate [J]. Tetrahedron: A-symmetry,2003,14:2683 - 2685.
  • 8Bereczki L, Bombicz P, Balint J, et al. Optical resolution of 1-(1-naphthyl) ethylamine by its dicarboxylic acid derivatives: Structural features of the oxalic acid derivative diastereomeric salt pair [J]. Chirality, 2009, 21:331 - 338.

共引文献3

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