Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2013 Jun 29;69(Pt 7):o1168.
doi: 10.1107/S1600536813017248. eCollection 2013.

2,6-Dimethyl-4-oxo-3-oxatri-cyclo-[5.2.1.0(2,6)]decane-1-carboxamide

Oleksandr Grytsai  1 , Marian Gorichko
Affiliations

2,6-Dimethyl-4-oxo-3-oxatri-cyclo-[5.2.1.0(2,6)]decane-1-carboxamide

Oleksandr Grytsai et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

In the title compound, C12H17NO3, which was synthesized by Wagner-Meerwein rearrangement of the N-nitro-imine, the ring-junction C-C bond length is comparatively long [1.573 (2) Å] due to a steric repulsion between the methyl groups at these atoms, which also leads to an increase in the C-C-C angles along this C4 chain [118.10 (13) and 115.04 (15) °, respectively]. In the crystal, N-H⋯O-C and N-H⋯O=C hydrogen bonds are formed between the amide group and the two O-atom acceptors of the lactone group, forming a chain along [001].

PubMed Disclaimer

Figures

Fig. 1.
Fig. 1.
The molecular structure and atom nunbering scheme for the title compound, showing 30% probability displacement ellipsoids.
Fig. 2.
Fig. 2.
The synthetic route to the title compound (II).
See this image and copyright information in PMC

References

    1. Bondavalli, F., Bruno, O., Ranise, A., Schenone, P., Susanna, V., Lisa, M., Maione, S. & Marmo, E. (1987). Il Farmaco, 42, 947–953. - PubMed
    1. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
    1. Bruker (2008). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
    1. Bulman Page, P. C., Murrell, V. L., Limousin, C., Laffan, D. D. P., Bethell, D., Slawin, A. M. Z. & Smith, T. A. D. (2000). J. Org. Chem. 65, 4204–4207. - PubMed
    1. Knollmuller, M., Gartner, P., Ferencic, M., Noe, C. R. & Mereiter, K. (1998). Eur. J. Org. Chem. pp. 2507–2511.