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Adamantanone

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Adamantanone
Names
Preferred IUPAC name Adamantan-2-one
Other names Tricyclodecanone
2-Adamantanone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.772 Edit this at Wikidata
EC Number
  • 211-847-2
Gmelin Reference 122962
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2Key: IYKFYARMMIESOX-UHFFFAOYSA-N
SMILES
  • C1C2CC3CC1CC(C2)C3=O
Properties
Chemical formula C10H14O
Molar mass 150.221 g·mol
Appearance white solid
Melting point 270 °C (518 °F; 543 K)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H315, H318, H410
Precautionary statements P264, P270, P273, P280, P301+P310, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Adamantanone is the ketone of adamantane. A white solid, it is prepared by oxidation of adamantane. It is a precursor to several adamantane derivatives.

Adamantanone and some related polycyclic ketones, are reluctant to form enolates. This barrier arises because the resulting carbanion cannot exist in conjugation with the carbonyl pi-bond.

References

  1. Geluk, H. W.; Keizer, V. G. (1973). "Adamantanone". Organic Syntheses. 53: 8. doi:10.15227/orgsyn.053.0008.
  2. Fleming, Michael P.; McMurry, John E. (1981). "Reductive Coupling of Carbonyls to Alkenes: Adamantylideneadamantane". Organic Syntheses. 60: 113. doi:10.15227/orgsyn.060.0113.
  3. Meyer, Matthew M.; Kass, Steven R. (2010). "Enolates in 3-D: An Experimental and Computational Study of Deprotonated 2-Adamantanone". The Journal of Organic Chemistry. 75 (12): 4274–4279. doi:10.1021/jo100953y. PMID 20496940.
  4. Norlander, J.E.; Jindal, S.; Kitko, D. (1969). "Resistance of Adamantanone to Homoenolization". Journal of the Chemical Society, Chemical Communications (19): 1136–1137. doi:10.1039/C29690001136.
  5. Stothers, J.B.; Tan, C.T. (1974). "Adamantanone: stereochemistry of its homoenolization as shown by H nuclear magnetic resonance". Journal of the Chemical Society, Chemical Communications (18): 378–379. doi:10.1039/C39740000738.
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