Ethyl (4aR*,7S*,8S*,8aS*)-1-oxo-7-phenyl-3,4,4a,7,8,8a-hexa­hydro-1H-isochromene-8-carboxyl­ate

Jiang, X.Q.; Wu, J.-L.

doi:10.1107/S1600536810017009

Volume 66
Part 6
Page o1367
June 2010

Received 30 April 2010
Accepted 10 May 2010
Online 15 May 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.069
wR = 0.197
Data-to-parameter ratio = 15.8
Details

Ethyl (4aR,7S,8S,8aS)-1-oxo-7-phenyl-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate

Xiu Qing Jiang ^a and Jin-Long Wu ^a ^*

^aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China
Correspondence e-mail: wyz@zju.edu.cn

In the title compound, C₁₈H₂₀O₄, both the tetrahydropyranone ring and the cyclohexene ring adopt envelope conformations. The crystal packing is stabilized by weak intermolecular C-HO hydrogen bonding.

Related literature

The title compound is a derivative of 1-oxo-hexahydro-1H-isochromene, which has been reported as a key intermediate towards the total syntheses of natural products such as eleutherobin and tetronothiodin, see: Kim et al. (2000); Jung et al. (2000); Page et al. (2003). For microwave-assisted intramolecular Diels-Alder cycloaddition, see: Wu et al. (2006, 2007); Wang et al. (2009).

Experimental

Crystal data

C₁₈H₂₀O₄
M_r = 300.34
Orthorhombic, P b c a
a = 15.5513 (12) Å
b = 9.9178 (7) Å
c = 21.1542 (17) Å
V = 3262.7 (4) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.36 × 0.16 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
26140 measured reflections
3200 independent reflections
1627 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.197
S = 1.00
3200 reflections
202 parameters
1 restraint
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1O4ⁱ	0.98	2.45	3.401 (4)	164
C5-H5AO4ⁱ	0.97	2.48	3.412 (4)	161
C7-H7O1ⁱⁱ	0.93	2.56	3.468 (5)	165
C13-H13O2ⁱⁱⁱ	0.93	2.59	3.356 (6)	140
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2757 ).

Acknowledgements

This work is supported by the Natural Science Foundation of China (grant No. 20572092). Professor Wei-Min Dai is thanked for his valuable suggestions on this work. Mr Jianming Gu of the X-ray crystallography facility of Zhejiang University is acknowledged for his assistance with the crystal structure analysis.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Jung, M. E., Huang, A. & Johnson, T. W. (2000). Org. Lett. 2, 1835-1837.
Kim, P., Nantz, M. H., Kurth, M. J. & Olmstead, M. M. (2000). Org. Lett. 2, 1831-1834.
Page, P. C. B., Vahedi, H., Batchelor, K. J., Hindley, S. J., Edgar, M. & Beswick, P. (2003). Synlett, pp. 1022-1024.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y., Wu, J. & Dai, W.-M. (2009). Synlett, pp. 2862-2866.
Wu, J., Sun, L. & Dai, W.-M. (2006). Tetrahedron, 62, 8360-8372.
Wu, J., Yu, H., Wang, Y., Xing, X. & Dai, W.-M. (2007). Tetrahedron Lett. 48, 6543-6547.

organic compounds

Ethyl (4aR*,7S*,8S*,8aS*)-1-oxo-7-phenyl-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate