[1]罗光顺.保护-烷基化-脱保护法制备脂肪仲胺[J].华侨大学学报(自然科学版),2010,31(5):539-541.[doi:10.11830/ISSN.1000-5013.2010.05.0539]
　LUO Guang-shun.Synthesis of Secondary Fatty Amines via Protection-Alkylation-Deproection Process[J].Journal of Huaqiao University(Natural Science),2010,31(5):539-541.[doi:10.11830/ISSN.1000-5013.2010.05.0539]
点击复制

保护-烷基化-脱保护法制备脂肪仲胺()
分享到：

《华侨大学学报（自然科学版）》[ISSN:1000-5013/CN:35-1079/N]

卷:
第31卷
期数:
2010年第5期
页码:
539-541
栏目:
出版日期:
2010-09-20

文章信息/Info

Title:
Synthesis of Secondary Fatty Amines via Protection-Alkylation-Deproection Process
文章编号:
1000-5013(2010)05-0539-03
作者:
罗光顺
华东理工大学药学院
Author(s):
LUO Guang-shun
School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
关键词:
仲胺化合物;  对甲苯磺酰胺;  烷基化;  脱保护;  DMFDMA
Keywords:
secondary amine;  p-toluene sulfonamide;  alkylation; deprotection;  DMFDMA
分类号:
TQ226.31
DOI:
10.11830/ISSN.1000-5013.2010.05.0539
文献标志码:
A
摘要:
以对甲苯磺酰胺为原料,经烷基化、镁/甲醇脱去磺酰基保护基制备对称仲胺化合物,合成了9个脂肪仲胺化合物,产率达90%,产品结构经核磁共振氢谱得到确证.将合成的二苄基胺与N,N-二甲基甲酰胺二甲基缩醛进行胺交换反应,制备N,N-二苄基甲酰胺二甲基缩醛(DMFDMA),扩大了该方法的应用范围.
Abstract:
A series of secondary amines were synthesized via alkylation and deprotection of p-toluene sulfonamide with a yield of 90% in two steps.The structures of the secondary amines were confirmed by 1H NMR spectroscopy.Reacting the synthesized dibenzyl amine with DMFDMA gave N,N-dibenzyl formamide dimethyl acetal,which expanded the application scope of this method.

参考文献/References:

[1] GHOSE A K, VISWANADHAN V N, WENDOLOSKI J J. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery (Ⅰ):A qualitative and quantitative characterization of know drug database [J]. Journal of Combinatorial Chemistry, 1999(1):55-68.doi:10.1021/cc9800071.
[2] PORCHEDDU A, GIACOMELLIi G, PIREDDA I. Parallel synthesis of trisubstitued formamidines:A facile and versatile procedure [J]. Journal of Combinatorial Chemistry, 2009(1):126-130.doi:10.1021/cc8001124.
[3] INSASF S S, WITIAK D T. Facile non-racemizing route for the N-alkylation of hindered secondary amines [J]. Journal of Synthetic Organic Chemistry Japan, 1999(3):435-440.doi:10.1055/s-1999-3399.
[4] SWAMMURA M, ITO Y. Catalytic asymmetric synthesis by means of secondary interaction between chiral ligands and substrates [J]. Chemical Reviews, 1992(5):857-871.
[5] HENKEL T, BRUNNE R M, MUELLER H. Statistical investigation into the structural comple mentarity of natural products and synthetic compounds [J]. Angewandte Chemie International Edition in English, 1999(5):643-647.doi:10.1002/(SICI)1521-3773(19990301)38:5< 643::AID-ANIE643> 3.0.CO; 2-G.
[6] 凌青, 李欣, 沈竞康. 仲胺的合成方法新进展 [J]. 合成化学, 2007(3):247-253.doi:10.3969/j.issn.1005-1511.2007.03.001.
[7] MCVRIDE L J, KIERZEK R, BEAUCAGE S L. Nucleotide chemistry (16):Amidine protecting groups for oligonucleotide synthesis [J]. Journal of the American Chemical Society, 1986(8):2040-2048.doi:10.1021/ja00268a052.
[8] KER S G, KALMAN T I. Highly water-soluble lipophilic prodrugs of the anti-HIV nucleoside analogue 2’, 3’-dideoxycytidine and its 3’-fluoro derivative [J]. Journal of Medicinal Chemistry, 1992, (11):1996-2001.
[9] 华东理工大学有机化学教研组. 有机合成中的保护基 [M]. 上海:华东理工大学出版社, 2004.604-607.
[10] NYASSE B, GREHN L, RAGNARSSON U. Mild, efficient cleavage of arenesulfonamides by magnesium reduction [J]. Chemical Communications, 1997.1017-1018.doi:10.1039/a701408b.

备注/Memo

备注/Memo:
国家自然科学基金资助项目(30721005)
更新日期/Last Update: 2014-03-23