期刊文献+

用循环拆分法制备手性萘乙胺 被引量:4

Preparation of Chiral Naphthylethylamines by Recycling Resolution
下载PDF
导出
摘要 研究了1-(1-萘基)乙胺[(RS)-1]和1-(2-萘基)乙胺[(RS)-2]的循环拆分方法。以D-酒石酸为拆分剂,分别拆分(RS)-1和(RS)-2得到了(R)-1-(1-萘基)乙胺(收率31%,98%ee)和(R)-1-(2-萘基)乙胺(收率30%,98%ee),并对母液中的非目标对映异构体成功的进行了消旋化,实现了循环拆分。 The recycling resolution of (RS) -1 - ( 1 -naphthyl ) ethylamine [ ( RS ) -1 ] and ( RS ) -1 - ( 2 - naphthyl) ethylamine [ (RS) -2 ] was studied in this paper. (R) -1 - ( 1 -naphthyl ) ethylamine ( 31% yield, 98%ee) and (R)-1-(2-naphthyl) ethylamine(30% yield, 98% ee) were obtained via resolution of the racemic (RS) -1 and (RS) -2 by using D-tartaric acid as a resoluting agent. Meanwhile racemization of the non-target enantiomeric isomers from mother liquor was performed, and the recycling resolution was realized.
出处 《合成化学》 CAS CSCD 北大核心 2010年第1期61-63,共3页 Chinese Journal of Synthetic Chemistry
基金 国家自然科学基金资助项目(20972048) 上海市教育发展基金资助项目(03SG27)
关键词 萘乙胺 拆分 循环拆分 消旋 naphthylethylamine resolution recycling resolution racemization
  • 相关文献

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.

同被引文献55

  • 1钟荣,杨建文,曾兆华,陈用烈.芳酮季铵盐光产碱剂的合成与表征[J].中山大学学报(自然科学版),2006,45(1):53-57. 被引量:2
  • 2李宪平,梅光泉,黄可龙,罗勤慧.2,2′,2″-三氨基乙基胺-咪唑的对称异双核配合物的合成及电化学性质[J].化学试剂,2006,28(8):451-454. 被引量:5
  • 3章思规 辛忠.精细有机化工制备手册[M].北京:科学技术文献出版社,1996..
  • 4Thiei 0 R, Bernard C, Tormos W, et al. Practical synthesis of the ealeimimetie agent, elnaealect[J].Tetrahedron Letters, 2008, 49: 13-15.
  • 5Yamada H, Kawate T, Nishida A, et al. Asymmetric addition of alkyllithium to chiral Imines: 1-Naphthylethyl group as a (hiral auxiliary [ J]. Journal of Organic Chemistry, 1999, 64 : 882l -8828.
  • 6Baddely G. Acylation of naphthalene by the Friedel-Crafts reaction [J]. J Chem Soc,1949(1):99-103.
  • 7胡键.手性萘乙胺和拟钙剂cinacalcet的合成[D].上海:华东理工大学药学院,2010.
  • 8孔祥文.有机化学[M].北京:化学工业出版社,2010:114.
  • 9Lapkin I I, Lyuhimova A V. Steric hindrance in organomagnesium reactions. IX. Preparation of ketones by reaction of acyl halides with organomagnesium compounds[J].Zhurnal Obshchei Khimii, 1949. 19,707-16.
  • 10段行信.实用精细有机合成手册[M].北京:化学工业出版社,2001.297.

引证文献4

二级引证文献6

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