[Synthesis and spectral analysis of three kinds of epoxy pregnene derivatives].

ABSTRACT

Three kinds of derivatives, 16alpha, 17alpha-epoxy-6-methylene-pregn-4-ene-3,20-dione(EMPD I), 16alpha, 17alpha-epoxy-6-methyl-pregn-4,6-diene-3,20-dione (EMPD II) and 16alpha, 17alpha-epoxy-6-methyl-pregn-4-ene-3, 20-dione(EMPD III) were synthesized and their FTIR, UV and 1H NMR spectra were described. EMPD II is a novel compound. In the UV spectra, the maximum absorptions peaks of EMPD I, EMPD II and EMPD III are at 259, 287 and 239 nm respectively. Their IR spectra are also obviously different. For EMPD I, there are two absorption peaks, which are respectively at 3084 cm(-1) originated from ==CH2 and 3 030 cm(-1) from C==CH--. For EMPD II and III, there is only one absorption peak at 3054 cm(-1). From 1710-1660 cm(-1), only one absorption peak appears for EMPD III, but two appear for EMPD I and EMPD II. In 1H NMR spectrum, the peaks at 4.92 (s, 1H), 5.06 (s, 1H) and 5.88 (s, 1H) were observed for EMPD I; the peaks at 1.83 (s, 3H), 5.87 (s, 1H) and 5.85 (s, 1H) for EMPD II; while the peaks at 1.06-1.07 (d, 3H), 5.78 ppm (s, 1H, 1 ppm=l nicrog x mL(-1)), for EMPD III.