Synthesis, structural and conformational study of chromane derivatives

被引：6

作者：

Ciolkowski, Michal ^{[1
]}

Malecka, Magdalena ^{[2
]}

Modranka, Roman ^{[3
]}

Budzisz, Elzbieta ^{[1
]}

机构：

[1] Med Univ Lodz, Fac Pharm, Dept Cosmet Raw Mat Chem, PL-90151 Lodz, Poland

[2] Univ Lodz, Dept Crystallog & Crystal Chem, PL-90236 Lodz, Poland

[3] Med Univ Lodz, Fac Pharm, Dept Bioorgan Chem, PL-90151 Lodz, Poland

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2009年 / 937卷 / 1-3期

关键词：

Synthesis; Chromane derivatives; H-1 NMR study; X-ray structure; DFT calculation; DENSITY-FUNCTIONAL THEORY; SPIN COUPLING-CONSTANTS; AB-INITIO; COUMARIN DERIVATIVES; VITAMIN-E; STEREOCHEMISTRY; MODEL; REDUCTION; AMINES;

D O I：

10.1016/j.molstruc.2009.08.028

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

2-Methyl-4-oxo-4H-chromene-3-carboxylic acid methyl ester (1) and 2-phenyl-4-oxo-4H-chromene-3-carboxylic acid ethyl ester (2) were reacted with NaBH4 to give 2-R-2,3-dihydro-4-hydroxy-2H-1-benzopyran-3-carboxylic acid esters (3: methyl ester, R = methyl, 4: ethyl ester, R = phenyl - respectively). The structures of resultant compounds 3 and 4 were confirmed by IR, H-1 NMR spectroscopy, mass spectrometry and elemental analysis. Additionally the X-ray analysis of the Compound 3 revealed that hydrogen atoms bonded to the C2 and C4 atoms are in axial positions and hydrogen atom bonded to C3 atom is in equatorial position. The main conformation in Solution for both compounds is similar and was confirmed based on the (3)J(HH) coupling constants obtained from experimental spectra and from DFT conformational analysis. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：139 / 145

页数：7

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