Artículos de revistas
Self-association And Stereochemistry Study Of (5r)-4-methyl-5-phenyl-1,3,4- Oxadiazinan-2-one
Registro en:
Zeitschrift Fur Kristallographie. , v. 221, n. 3, p. 226 - 230, 2006.
442968
10.1524/zkri.2006.221.3.226
2-s2.0-33644767861
Autor
Rodrigues A.
Olivato P.R.
Zukerman-Schpector J.
Rittner R.
Institución
Resumen
C10H12N2O2, Mr = 191.21, P21, a = 5.5771(7), b = 27.841(3), c = 6.906(1) A°, β = 111.937(9)°, Z = 4, R1 = 0.0462. The two independent molecules in the asymmetric unit are linked through two very strong quasi centrosymmetric hydrogen bonds. The oxadiazinone rings, of both molecules, show the pyramidal inversion at N-4 nitrogen, thus resulting in a C (R)N(S)-C(R)N(R) diastereomeric pair. The analysis of the IR N-H stretching band (in the solid and in carbon tetrachloride solution) and the 13C NMR experiment at low temperature are in agreement with the X-ray crystal structure. © by Oldenbourg Wissenschaftsverlag. 221 3 226 230 Trepanier, D.L., Elbe, J.N., Harris, G.H., Synthesis and pharmacological evaluation of some Tetrahydrooxadiazinones and some Dihydroaminooxadiazines (1968) J. Med. Chem., 11, pp. 357-360 Trepanier, D.L., Harris, G.H., (1969) Chem. Abstr., 70, pp. 78026c. , Substituted 3,4,5,6-tetrahydro2H-1,3,4-oxadiazin-2-one compounds. US Patent 3,377,345, 1968 Casper, D.M., Burgeson, J.R., Esken, J.M., Ferrence, G.M., Hitchcock, S.R., Toward the development of a structurally novel class of chiral auxiliaries: Diastereoselective aldol reactions of a (1R,2S)-Ephedrine-Based 3,4,5,6-Tetrahydro-2H-1,3,4-oxadiazin-2-one (2002) Org. Lett., 4, pp. 3739-3742 Casper, D.M., Hitchcock, S.R., An improved procedure for the asymmetric aldol reaction of the titanium enolate of an N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2- one (2003) Tetrahedron: Asymmetry, 14, pp. 517-521 Hoover, T.R., Hitchcock, S.R., Oxadiazinones as chiral auxiliaries: Diastereoselective aldol addition reactions of N3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones (2003) Tetrahedron: Asymmetry, 14, pp. 3233-3241 Burgeson, J.R., Renner, M.K., Haradt, I., Ferrence, G.M., Standard, J.M., Hitchcock, S.R., Toward the development of a structurally novel class of chiral auxiliaries. Conformal properties of the aldol adducts of oxadiazinones: Observation of unusual shielding effects (2004) J. Org. Chem., 69, pp. 727-734 Rodrigues, A., Olivato, P.R., Rittner, R., Synthesis of (5R)-4-methyl-1,3,4-oxadiazinan-2-one and some N-acyl derivatives from (R)-phenylglycine (2005) Synthesis, pp. 2578-2582 Hitchcock, S.R., Nora, G.P., Casper, D.M., Squire, M.D., Maroules, C.D., Ferrence, G.M., Szczepura, L.F., Standard, J.M., X-ray crystallographic and 13C nuclear magnetic resonance studies of 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from ephedrine and pseudoephedrine (2001) Tetrahedron, 57, pp. 9789-9798 Szczepura, L.F., Hitchcock, S.R., Nora, G.P., (5S,6R)-3,4,5,6-Tetrahydro-5-methyl-6-phenyl-4-propyl-2H-1,3, 4-oxadiazin-2-one (2004) Acta Cryst., E60, pp. o1467-o1469 Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Completition and refinement of crystal structures with SIR92 (1993) J. Appl. Cryst., 26, pp. 343-350 Sheldrick, G.M., (1997) SHELXL97. Programs for Crystal Structure Analysis (Release 97-2), , University of Göttingen, Germany Nardelli, M., An update to PARST: A system of fortran routines for calculating molecular structure parameters from the results of crystal structure analyses (1995) J. Appl. Cryst., 28, p. 659 Spek, A.L., (1998) PLATON. A Multipurpose Crystallographic Tool, , Utrecht University, The Netherlands Farrugia, L.J., WinGX suite for small-molecule single-crystal crystallography (1999) J. Appl. Cryst., 32, pp. 837-838 Iulek, J., Zukerman-Schpector, J., CONFORMA. A program for calculating puckering parameters (1997) Quim. Nova, 20, pp. 433-434 Farrugia, L.J., ORTEP 3 - A program for ellipsoid presentation of crystal structures (1997) J. Appl. Cryst., 30, p. 565 Allen, F.H., The Cambridge Structure Database: A quarter of a million crystal structures and raising (2002) Acta Cryst., B58, pp. 380-388 Bruno, I.J., Cole, J.C., Edgington, P.R., Kessler, M., Macrae, C.F., McCabe, P., Peterson, J., Taylor, R., ConQuest: New software for searching the Cambridge Structure Database and visualizing crystal structures (2002) Acta Cryst., B58, pp. 389-397 Cremer, D., Pople, J.A., General definition of ring puckering coordinates (1975) J. Am. Chem. Soc., 97, pp. 1354-1358 Bellamy, L.J., (1968) Advances in Infrared Group Frequencies, pp. 283-287. , Chapman & Hall, London Vinogradov, S.N., Linnell, R.H., (1971) Hydrogen Bonding, pp. 161-163. , VNR Company, first ed