(-)-2-(N-正丙基氨基)-5-羟基四氢化萘的合成

左洪剑1;杜洪光1*;李明1;刘喜全2;杜振涛2;王树明2

北京化工大学学报(自然科学版) ›› 2007, Vol. 34 ›› Issue (6) : 575-578.

PDF(618 KB)
欢迎访问北京化工大学学报(自然科学版),今天是 2025年2月19日 星期三
Email Alert  RSS
PDF(618 KB)
北京化工大学学报(自然科学版) ›› 2007, Vol. 34 ›› Issue (6) : 575-578.
材料科学与工程

(-)-2-(N-正丙基氨基)-5-羟基四氢化萘的合成

  • 左洪剑;杜洪光*;李明;刘喜全;杜振涛;王树明
作者信息 +

Synthesis of (-)-5-hydroxy-2-(N-propylamino)tetralin

  • ZUO HongJian1;DU HongGuang1;LI Ming1;LIU XiQuan2;DU ZhenTao2;WANG ShuMing2
Author information +
文章历史 +

摘要

以1,6-二甲氧基萘为原料,经Na/C2H5OH还原生成5-甲氧基-2-四氢萘酮,与正丙胺还原胺化生成外消旋化合物2-(N-正丙基氨基)-5-甲氧基四氢化萘,经拆分得到手性的化合物(-)-2-(N-正丙基氨基)-5-甲氧基四氢化萘,再去甲基反应得到化合物(-)-2-(N-正丙基氨基)-5-羟基四氢化萘。采用元素分析、红外光谱、1H-NMR和13C-NMR表征了中间体和产物的分子结构。通过合成工艺的研究,得到较好的工艺条件,反应总收率达16.8%。采用一步法的还原胺化反应,不仅简化了反应步骤,而且收率提高了16.2%。

Abstract

Reduction of 1,6-dimethoxynaphthalene with Na/EtOH afforded 5-methoxy-2-tetralone. Racemic 5-methoxy-2-(N-propylamino)tetralin was subsequently prepared by a reductive amination reaction using n-propylamine and the racemic mixture successfully resolved to give the chiral compound (-)-5-methoxy-2-(N-propylamino)tetralin, which was finally converted to (-)-5-hydroxy-2-(N-propylamino) tetralin via a demethylation reaction. By means of a systematic study, the optimum conditions were identified; the maximum observed overall yield was 16.8%. Furthermore it was found that by using a one-step reductive amination reaction, not only was the synthesis shortened, but the yield was enhanced by 16.2%. Structures of intermediate compounds and the final product were characterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectroscopy

引用本文

导出引用
左洪剑1;杜洪光1*;李明1;刘喜全2;杜振涛2;王树明2. (-)-2-(N-正丙基氨基)-5-羟基四氢化萘的合成[J]. 北京化工大学学报(自然科学版), 2007, 34(6): 575-578
ZUO HongJian1;DU HongGuang1;LI Ming1;LIU XiQuan2;DU ZhenTao2;WANG ShuMing2. Synthesis of (-)-5-hydroxy-2-(N-propylamino)tetralin[J]. Journal of Beijing University of Chemical Technology, 2007, 34(6): 575-578

参考文献

[1]VLIET L A, TEPPER P G, DIJKSTRA D, et al. Affinity for dopamine D2, D3, and D4 receptors of 2-aminotetralins.Relevance of D2 agonist binding for determination of receptor subtype selectivity[J]. J Med Chem, 1996, 39: 4233-4237
[2]DUTTA A K, ALOKE K. Derivatives of 2-aminotetralins and pharmaceutical
analogs there of exhibiting differential cns receptor activity and behavior: US
2003225154[P]. 2003-12-04
[3]TIMMERMAN W, RUSK I N, TEPPER P, et al. The effects of the enantiomers of the dopamine agonist N0437 on food consumption and yawning behaviour in rats [J]. European Journal of Pharmacology, 1989, 174: 107-114
[4]SONESSON C, BARF T, NILSSON J, et al. Synthesis and evaluation of pharmacokinetic properties of monopropyl analogs of 5-,7-,and 8-[[(trifluoromethyl)sulfonyl]oxy]-2-aminotetralins: Central dopamine and serotonin receptor activity[J]. J Med Chem, 1995, 38: 1319-1329
[5]SEILER M P, STOLL A P, CLOSSE A, et al. Structureactivity relationships
of dopaminergic 5hydroxy2aminotetralin derivatives with functionalized N-alkyl-substituents[J]. J Med Chem, 1986, 29: 912-917
[6]CORNFORTH J W, ROBINSON S R. Experiments on the synthesis of substances related of the sterols. Part XLVIII. Synthesis of a tricyclic degradation product of cholesterol[J]. J Chem Soc, 1949: 1855-1865.
[7]ZIJLSTRA S, ELSINGA P H, OOSTERHUIS E Z, et al. Synthesis and in vivo
distribution in the rat of several fluorine-18 labeled 5-hydroxy-2-aminotet
ralin derivativees[J]. Appl Radiat Isot, 1993, 44(3): 473-480
[8]AMES D E, EVANS D, GREY T F, et al. The synthesis of alkoxy-1,2,3,4-tetrahydronaphthalene derivatives. Part I. 2-amino-, alkylamino-, and dialkylamino-derivatives[J]. J Chem Soc, 1965: 2636-2641
[9]HACKSELL U, SVENSSON U, NILSSON J G. Nalkyl-ated 2-aminotetralins: Central dopaminereceptor stimulating activity[J]. J Med Chem, 1979, 22: 1469-1475.
[10]BAKTHAVACHALAM V, BAINDUR N, MADRAS B K, et al. Fluorescent probes for dopamine receptors: Synthesis and characterization of fluorescein and 7-nitrobenz-2-oxa-1,3-diazol-4-yl conjugates of D-1 and D-2 receptor ligands[J]. J Med Chem, 1991, 34: 3235-3241.
PDF(618 KB)

3186

Accesses

0

Citation

Detail

段落导航
相关文章

/