新型酰胺型手性大环多胺的合成及光谱表征

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Abstract Two novel chiral macrocyclic dioxopolyamines,which can be used as NMR chiral solvating agents (CSAs) for chiral carboxylic acids,were synthesized from L-proline through esterification,bridging and ring-closing reaction. With the aid of orthogonal experiments the optimum reaction conditions were determined: for (8S,18S)-1,4,10,13,16-pentaaza-tricyclo[16.3.0.0^4,8]heneicosane-9,17-dione(2-a),reaction temperature 50 ℃,reaction time 10 d,in nitrogen atmosphere,absolute MeOH,yield 34.9%,and m.p. 278-280 ℃;for 13-phenyl-(8S,18S)-1,4,10,13,16-pentaaza-tricyclo [16.3.0.0^4,8]heneicosane-9,17-dione (2-b),reaction temperature at reflux,reaction time 20 d,in nitrogen atmosphere,absolute MeOH,yield 2.6%,and m.p. 243-245 ℃. Their molecular structures were characterized by elemental analysis (EA),mass spectroscopy (MS),infrared spectroscopy (IR),and 1D and 2D nuclear magnetic resonance spectrometry (NMR). The main infrared absorption peaks and nuclear magnetic spectral bands of the compounds were assigned. The spectroscopic analytical result provides useful information for further study of the mechanism of host-guest interaction and for preparing new and effective CSAs.

Key words：Chiral macrocyclic dioxopolyamines;L-proline;Synthesis;NMR;IR;MS

Received: 2006-10-28 Accepted: 2007-01-26

ZTFLH:

O621.1

Corresponding Authors: FU En-qin E-mail: fueq@whu.edu.cn

Cite this article:

YANG Xue-mei,FU En-qin. Synthesis and Spectral Characterization of Novel Chiral Macrocyclic Dioxopolyamines[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2007, 27(07): 1403-1407.

URL:

https://www.gpxygpfx.com/EN/Y2007/V27/I07/1403

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