Cyclooctyne is the cycloalkyne with a formula C
8
H
12
. Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one triple bond.

Cyclooctyne
Identifiers
3D model (JSmol)
1209275
ChEBI
ChemSpider
UNII
  • InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-6H2
    Key: ZPWOOKQUDFIEIX-UHFFFAOYSA-N
  • C1CCCC#CCC1
Properties
C8H12
Molar mass 108.184 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclooctyne is the smallest cycloalkyne that is stable enough to be isolated, although the chemical is still highly reactive. The alkyne region of the structure attempts to adopt a linear molecular geometry, but the nature of the ring creates substantial ring strain. As a result, cyclooctyne and other compounds containing this ring structure readily react in ways that reduce the ring strain by converting the alkyne to a functional group that does not require linear geometry. An important application of this reactivity is in click chemistry, where cyclooctynes undergo cycloaddition reactions with azides[1] or nitrones,[2] forming triazoles or isoxazolines, respectively.

References

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  1. ^ Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. (2007). "Copper-free click chemistry for dynamic in vivo imaging". Proceedings of the National Academy of Sciences. 104 (43): 16793–7. Bibcode:2007PNAS..10416793B. doi:10.1073/pnas.0707090104. PMC 2040404. PMID 17942682.
  2. ^ Ning, Xinghai; Temming, Rinske P.; Dommerholt, Jan; Guo, Jun; Blanco-Ania, Daniel; Debets, Marjoke F.; Wolfert, Margreet A.; Boons, Geert-Jan; Van Delft, Floris L. (2010). "Protein Modification by Strain-Promoted Alkyne-Nitrone Cycloaddition". Angewandte Chemie International Edition. 49 (17): 3065–8. doi:10.1002/anie.201000408. PMC 2871956. PMID 20333639.
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