Hostname: page-component-cd9895bd7-8ctnn Total loading time: 0 Render date: 2024-12-26T08:26:45.660Z Has data issue: false hasContentIssue false
  • English
  • Français

Synthesis and X-ray diffraction data of 4-benzyloxy-1-oxaspiro-[4.6]-undec-3-en-2-one

Published online by Cambridge University Press:  17 December 2013

Jose H. Quintana ,
J. A. Henao ,
Elvis Robles  and
Juan Manuel Urbina
Jose H. Quintana
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Centro de Investigación en Biomoléculas, (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
J. A. Henao
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Centro de Investigación en Biomoléculas, (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
Elvis Robles
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
Juan Manuel Urbina
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
Get access Rights & Permissions [Opens in a new window]

Abstract

The 4-benzyloxy-1-oxaspiro-[4.6]-undec-3-en-2-one (C17H20O3) was prepared through a domino reaction from benzyl α-hydroxycycloheptanecarboxylate and the cumulated ylide Ph3P=C=C=O by: (i) addition and (ii) intramolecular Wittig Olefination reaction. The reaction was carried out using anhydrous toluene as solvent under an argon atmosphere in a Schlenk flask. Molecular characterization was performed by Fourier transform infrared spectroscopy, gas chromatography-mass spectrometry, (1H,13C – mono and bidimensional) nuclear magnetic resonance spectroscopy; crystallographic characterization was completed by X-ray diffraction of polycrystalline samples (XRPD). The title compound crystallized in a monoclinical system and unit-cell parameters are reported [a = 13.207(3) Å, b = 5.972(1) Å, c = 19.719(4) Å, β = 105.67(2)°, unit-cell volume V = 1497.5 (4) Å3, Z = 4]. All of the measured lines were indexed with the P21/n (No. 14) space group.

Keywords

O-Bencyl tetronateX-ray powder diffraction dataspiro tetronic acid
Type
New Diffraction Data
Information
Powder Diffraction , Volume 28 , Issue 4 , December 2013 , pp. 315 - 320
Copyright
Copyright © International Centre for Diffraction Data 2013 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Boultif, A. and Louër, D. (2006). “Indexing of powder diffraction patterns of low symmetry lattices by successive dichotomy method,” J. Appl. Crystallogr. 37, 724–731.Google Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern,” J. Appl. Crystallogr. 1, 108–113.Google Scholar
Dong, C. (1999). “PowderX: Windows-95-based program for poder X-ray diffraction data processing,” J. Appl. Crystallogr. 32, 838–838.CrossRefGoogle Scholar
Laugier, J. and Bochu, B. (2002). CHEKCELL. “LMGP-Suite Suite of Programs for the interpretation of X-ray. Experiments,” ENSP/Laboratoire des Matériaux et du Génie Physique, BP 46. 38042 Saint Martin d'Hères, France. http://www.inpg.fr/LMGP and http://www.ccp14.ac.uk/tutorial/lmgp/.Google Scholar
Mighell, A. D., Hubberd, C. R. and Stalick, J. K. (1981). “NBS* AIDS80: A FORTRAN program for crystallographic data evaluation,” National Bureau of Standards (USA), Technical Note 1141.Google Scholar
Rachinger, W. A. (1948). “A correction for the α 1 α 2 Doublet in the measurement of widths of X-ray diffraction lines,” J. Sci. Instrum. 25, 254.CrossRefGoogle Scholar
Savitzky, A. and Golay, M. J. (1964). “Smoothing and differentiation of data by simplified least squares procedures,” Anal. Chem. 36, 1627–1639.CrossRefGoogle Scholar
Schobert, R. (2007). “Domino syntheses of bioactive tetronic and tetramic acids,” Naturwissenschaften 94, 1–11.Google Scholar
Smith, G. S. and Snyder, R. L. (1979). “ F N : a criterion for rating powder diffraction patterns and evaluating the reliability of powder-pattern indexing,” J. Appl. Crystallogr. 12, 60–65.Google Scholar
Sonnerveld, E. J. and Visser, J. W. (1975). “Automatic collection of powder diffraction data from photographs,” J. Appl. Crystallogr. 8, 1–7.CrossRefGoogle Scholar
Tejedor, D. and García-Tellado, F. (2004). “Synthesis and chemistry of tetronic acids,” Org. Prep. Proced. Int. 36, 35–59.CrossRefGoogle Scholar