[Journal logo]

Volume 67 
Part 8 
Page o2050  
August 2011  

Received 7 July 2011
Accepted 11 July 2011
Online 16 July 2011

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.102
Data-to-parameter ratio = 17.2
Details
Open access

(5S)-3-Chloro-4-diallylamino-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one

aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
Correspondence e-mail: wangwangzhaoyang@tom.com

The title compound, C20H30ClNO3, was obtained via a tandem asymmetric Michael addition-elimination reaction of (5S)-3,4-dichloro-5-(l-menthyloxy)-2(5H)-furanone and diallylamine in the presence of potassium fluoride. The molecular structure contains an approximately planar five-membered furanone ring [maximum atomic deviation = 0.0221 (3) Å] and a six-membered ring adopting a chair conformation.

Related literature

For the biological activity of 4-amino-2(5H)-furanones, see: Gondela & Walczak (2010[Gondela, E. & Walczak, K. Z. (2010). Eur. J. Med. Chem. 45, 3993-3997.]). For chemical, pharmaceutical and agrochemical applications of 3,4-amino-2(5H)-furanones, see: Tanoury et al. (2008[Tanoury, G. J., Chen, M.-Z., Dong, Y., Forslund, R. E. & Magdziak, D. (2008). Org. Lett. 10, 185-188.]); Kimura et al. (2000[Kimura, Y., Mizuno, T., Kawano, T., Okada, K. & Shimad, A. (2000). Phytochemistry, 53, 829-831.]). For the synthesis of optically pure 5-(l-menthyloxy)-3,4-dichloro-2(5H)-furanones, see: Song et al. (2009[Song, X.-M., Wang, Z.-Y., Li, J.-X. & Fu, J.-H. (2009). Chin. J. Org. Chem. 11, 1804-1810.]). For the use of intermediate chiral 5-S-(l-menthyloxy)-2(5H)-furanones, see: Hoffmann et al. (2006[Hoffmann, N., Bertrand, S., Marinkovi, S. & Pesch, J. (2006). Pure Appl. Chem. 78, 2227-2246.]).

[Scheme 1]

Experimental

Crystal data
  • C20H30ClNO3

  • Mr = 367.90

  • Orthorhombic, P 21 21 21

  • a = 8.4540 (17) Å

  • b = 11.722 (2) Å

  • c = 20.648 (4) Å

  • V = 2046.1 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 273 K

  • 0.23 × 0.20 × 0.16 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.954, Tmax = 0.968

  • 9931 measured reflections

  • 3950 independent reflections

  • 2923 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.102

  • S = 0.97

  • 3950 reflections

  • 230 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1677 Friedel pairs

  • Flack parameter: -0.06 (6)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2113 ).


Acknowledgements

The work was supported by the National Natural Science Foundation of China (grant No. 20772035) and the Natural Science Foundation of Guangdong Province, China (grant No. 5300082).

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gondela, E. & Walczak, K. Z. (2010). Eur. J. Med. Chem. 45, 3993-3997.  [ISI] [CrossRef] [ChemPort] [PubMed]
Hoffmann, N., Bertrand, S., Marinkovi, S. & Pesch, J. (2006). Pure Appl. Chem. 78, 2227-2246.  [ISI] [CrossRef] [ChemPort]
Kimura, Y., Mizuno, T., Kawano, T., Okada, K. & Shimad, A. (2000). Phytochemistry, 53, 829-831.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Song, X.-M., Wang, Z.-Y., Li, J.-X. & Fu, J.-H. (2009). Chin. J. Org. Chem. 11, 1804-1810.
Tanoury, G. J., Chen, M.-Z., Dong, Y., Forslund, R. E. & Magdziak, D. (2008). Org. Lett. 10, 185-188.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2011). E67, o2050  [ doi:10.1107/S1600536811027772 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.