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Synthesis and Structural Characterization of N-Hydroxy-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide
Corresponding Author(s) : Jian Li
Asian Journal of Chemistry,
Vol. 25 No. 2 (2013): Vol 25 Issue 2
Abstract
The compound N-hydroxy-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide (C8H7NO4, Mr = 181.15) was synthesized and characterized by elemental analysis, 1H NMR spectra, IR spectra and single crystal X-ray diffraction. The crystal belongs to orthorhombic, space group Pnma, with a = 10.9505(11), b = 10.7263(10), c = 6.4005(4) Å, b = 90.00º, V = 751.79(11) Å3, Z = 4, Dc = 1.600 g/cm3, l = 0.71073 Å, μ(MoKa) = 0.131 mm-1, F(000) = 376. The final refinement gave R = 0.0434, wR(F2) = 0.1074 for 702 observed reflections with I > 2s(I). The structure of the title compound comprises a racemic mixture of chiral molecules containing four stereogenic centres. X-Ray diffraction analysis reveals that the cyclohexane ring tends towards a boat conformation, the tetrahydrofuran ring and the dihydrofuran ring adopt envelope conformations.
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- M.F. Brana, A. Gradillas, A. Gomez, N. Acero, F. Llinares, D. MunozMingarrro, C. Abradelo, F. Rey-Stolle, M. Yuste, J. Campos, M.A. Gallo and A. Espinosa, J. Med. Chem., 47, 2236 (2004).
- S.M. Sondhi, R. Rani, P. Roy, S.K. Agrawal and A.K. Saxena, Bioorg. Med. Chem. Lett., 19, 1534 (2009).
- J. Kossakowski and M. Jarocka, Farmaco, 56, 785 (2001).
- L.P. Deng and Y.Z. Hu, J. Heterocycl. Chem., 44, 597 (2007).
- L.P. Deng, F.M. Liu and H.Y. Wang, J. Heterocycl. Chem., 42, 13 (2005).
- M.E. Hart,A.R. Chamberlin, C. Walkom, J.A. Sakoff and A. McCluskey, Bioorg. Med. Chem. Lett., 14, 969 (2004).
- G. Goksu, N. Ocal and D.E. Kaufmann, Molecules, 15, 1302 (2010).
- J. Li, Z.P. Liang and W.L. Zeng, Asian J. Chem., 23, 4918 (2011).
- Z.P. Liang and J. Li, Asian J. Chem., 23, 4918 (2011).
- Z.P. Liang and J. Li, Asian J. Chem., 25, 660 (2013).
- G.M. Sheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Gottingen, Germany (1996).
- G.M. Sheldrick, SHELXTL V 5.1 Software Reference Manual, Bruker AXS, Inc., Madison, Wisconsin, USA (1997).
- Siemens, SMART and SAINT, Area Detector Control and Integration Software. Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA (1996)
References
M.F. Brana, A. Gradillas, A. Gomez, N. Acero, F. Llinares, D. MunozMingarrro, C. Abradelo, F. Rey-Stolle, M. Yuste, J. Campos, M.A. Gallo and A. Espinosa, J. Med. Chem., 47, 2236 (2004).
S.M. Sondhi, R. Rani, P. Roy, S.K. Agrawal and A.K. Saxena, Bioorg. Med. Chem. Lett., 19, 1534 (2009).
J. Kossakowski and M. Jarocka, Farmaco, 56, 785 (2001).
L.P. Deng and Y.Z. Hu, J. Heterocycl. Chem., 44, 597 (2007).
L.P. Deng, F.M. Liu and H.Y. Wang, J. Heterocycl. Chem., 42, 13 (2005).
M.E. Hart,A.R. Chamberlin, C. Walkom, J.A. Sakoff and A. McCluskey, Bioorg. Med. Chem. Lett., 14, 969 (2004).
G. Goksu, N. Ocal and D.E. Kaufmann, Molecules, 15, 1302 (2010).
J. Li, Z.P. Liang and W.L. Zeng, Asian J. Chem., 23, 4918 (2011).
Z.P. Liang and J. Li, Asian J. Chem., 23, 4918 (2011).
Z.P. Liang and J. Li, Asian J. Chem., 25, 660 (2013).
G.M. Sheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Gottingen, Germany (1996).
G.M. Sheldrick, SHELXTL V 5.1 Software Reference Manual, Bruker AXS, Inc., Madison, Wisconsin, USA (1997).
Siemens, SMART and SAINT, Area Detector Control and Integration Software. Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA (1996)