Artículo
Giacopello, S.; Deluca, M.E.; Seldes, A.M. "Synthesis and NMR Studies of Some Steroidal Isoxazoles" (1992) Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences. 47(6):891-897
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Abstract:
A short synthesis of 17α-pregna-2,4-dien-[2,3-d]isoxazol-17β-ol (1) is described using mild reaction conditions and with a high overall yield. The equilibrium between keto-enolic forms has been studied by 1H NMR methods. Complete assignments o f all the resonances in the 1H and 16C NMR spectra o f Danazol have been made using a variety o f one and two-dimensional correlation methods. 13C NMR spectra of all the intermediate and related model compounds were also assigned. © 1992, Walter de Gruyter. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | Synthesis and NMR Studies of Some Steroidal Isoxazoles |
| Autor: | Giacopello, S.; Deluca, M.E.; Seldes, A.M. |
| Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellín 2, Ciudad Universitaria, (1428) Buenos Aires, Argentina |
| Palabras clave: | 17α-Pregna-2,4-dien-[2,3-d]isoxazol-17β-ol, Synthesis, NMR Spectra; Anabolic Agents; Isoxazolinic Steroids |
| Año: | 1992 |
| Volumen: | 47 |
| Número: | 6 |
| Página de inicio: | 891 |
| Página de fin: | 897 |
| DOI: | http://dx.doi.org/10.1515/znb-1992-0620 |
| Título revista: | Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences |
| Título revista abreviado: | Z. Naturforsch. Sect. B J. Chem. Sci. |
| ISSN: | 09320776 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09320776_v47_n6_p891_Giacopello |
Referencias:
- Wakefield, B.J., (1976) The Chemistry of Organolithium Compounds, , Chapter 2, Pergamon Press, Oxford
- Luche, J.L., Damiano, J.C., (1980) J. Am. Chem. Soc, 102, p. 7926
- Clinton, R.O., Manson, A.J., Stonner, F.W., Christiansen, R.G., Beyler, A.L., Potts, G.O., Arnold, A., (1961) J. Org. Chem, 26, p. 279
- Myerson, R.M., (1961) Am. J. Med. Sci, 732, p. 78
- Bhacca, N.S., Williams, D.H., (1964) Applications of NMR Spectroscopy in Organic Chemistry, , Chapter 4, Holden-Day Inc., San Francisco
- Garbisch, E.W., (1963) J. Am. Chem. Soc, 85, p. 1696
- The anisotropy effect of the benzene ring was estimated comparing the chemical shifts of the aldehydic proton of benzaldehyde (10.09 ppm) and cyclohexanecarboxaldehyde (9.78 ppm). The double bond effect was estimated by comparison between cyclohexanecarboxaldehyde (9.78 ppm) and 1-cyclohexenecarboxaldehyde (9.41 ppm); Bax, A., Summers, M.F., (1986) J. Am. Chem. Soc, 108, p. 2093
- Blunt, J.W., Stothers, J.B., (1977) Org. Magn. Reson, 9 (8), p. 439
- Ruzicka, L., Rosenberg, H.R., (1936) Helv. Chim. Acta, 19, p. 357
- Weisenborn, F.L., Remy, D.C., Jacobb, T.L., (1954) J. Am. Chem. Soc, 76, p. 552;
Citas:
---------- APA ----------
Giacopello, S., Deluca, M.E. & Seldes, A.M. (1992) . Synthesis and NMR Studies of Some Steroidal Isoxazoles. Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 47(6), 891-897.http://dx.doi.org/10.1515/znb-1992-0620
---------- CHICAGO ----------
Giacopello, S., Deluca, M.E., Seldes, A.M. "Synthesis and NMR Studies of Some Steroidal Isoxazoles" . Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences 47, no. 6 (1992) : 891-897.http://dx.doi.org/10.1515/znb-1992-0620
---------- MLA ----------
Giacopello, S., Deluca, M.E., Seldes, A.M. "Synthesis and NMR Studies of Some Steroidal Isoxazoles" . Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, vol. 47, no. 6, 1992, pp. 891-897.http://dx.doi.org/10.1515/znb-1992-0620
---------- VANCOUVER ----------
Giacopello, S., Deluca, M.E., Seldes, A.M. Synthesis and NMR Studies of Some Steroidal Isoxazoles. Z. Naturforsch. Sect. B J. Chem. Sci. 1992;47(6):891-897.http://dx.doi.org/10.1515/znb-1992-0620
