NMR ANALYSIS OF FLUORINATED CORTICOSTEROIDS RELATED TO FLUOCINONIDE - DETECTION OF LONG-RANGE H-1 F-19 COUPLINGS USING THE HETERONUCLEAR EQUIVALENT OF THE COSY EXPERIMENT

被引:21
作者
HUGHES, DW [1 ]
BAIN, AD [1 ]
ROBINSON, VJ [1 ]
机构
[1] SYNTEX LTD,MISSISSAUGA L5N 3X4,ONTARIO,CANADA
关键词
H-1; NMR; F-19; CORTICOSTEROIDS; H-1 F-19 LONG-RANGE COUPLING; HETERONUCLEAR COSY; H-1 F-19 2D CORRELATION;
D O I
10.1002/mrc.1260290417
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The analysis of the H-1 and F-19 NMR spectra of the corticosteroid fluocinonide and five related steroids is reported. The 500 MHz H-1 NMR spectra revealed several previously undetected long-range H-1 - F-19 coupling constants. These couplings were assigned by the application of the heteronuclear equivalent of the COSY pulse sequence. The fluorine substituent effects and long-range heteronuclear couplings were examined in relation to structures derived from molecular mechanics (MMX) calculations.
引用
收藏
页码:387 / 397
页数:11
相关论文
共 34 条
[1]   HETERONUCLEAR CHEMICAL-SHIFT CORRELATION BY FULLY COUPLED PHASE-SENSITIVE TWO-DIMENSIONAL NMR, A ROBUST EXPERIMENT [J].
BAIN, AD .
JOURNAL OF MAGNETIC RESONANCE, 1988, 77 (01) :125-133
[2]   EFFECT OF HYPERCONJUGATION ON GEMINAL SPIN-SPIN COUPLING CONSTANT [J].
BARFIELD, M ;
GRANT, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (13) :1899-&
[4]  
BHACCA NS, 1964, APPLICATIONS NMR SPE
[5]  
Booth H., 1969, PROGR NMR SPECTROSCO, V5, P149
[6]  
Bothner-By A.A., 1965, ADV MAGNETIC OPTICAL, VVolume 1, P195
[7]  
Croasmun W. R., 1987, METHODS STEREOCHEM A, V9, P387
[8]   STEROIDS .117. SPECTRA AND STEREOCHEMISTRY .2. LONG-RANGE SPIN-SPIN COUPLING BETWEEN FLUORINE AND STEROID ANGULAR METHYL PROTONS [J].
CROSS, AD ;
LANDIS, PW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (09) :1736-&
[10]  
CROSS AD, 1965, J AM CHEM SOC, V86, P4011