Misplaced Pages

Cyclooctyne

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Cyclooctyne
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1209275
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-6H2Key: ZPWOOKQUDFIEIX-UHFFFAOYSA-N
SMILES
  • C1CCCC#CCC1
Properties
Chemical formula C8H12
Molar mass 108.184 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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 or nitrones, forming triazoles or isoxazolines, respectively.

References

  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.

External links

Categories: