Chemistry:Adamantanone
From HandWiki
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| Names | |
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| Preferred IUPAC name
Adamantan-2-one | |
| Other names
Tricyclo[3.3.1.13,7]decanone
2-Adamantanone | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
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| DrugBank | |
| EC Number |
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| 122962 | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10H14O | |
| Molar mass | 150.221 g·mol−1 |
| Appearance | white solid |
| Melting point | 270 °C (518 °F; 543 K) |
| Hazards | |
| GHS pictograms |   
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| GHS Signal word | Danger |
| H301, H315, H318, H410 | |
| P264, P270, P273, P280, P301+310, P302+352, P305+351+338, P310, P321, P330, P332+313, P362, P391, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
Adamantanone is the ketone of adamantane. A white solid, it is prepared by oxidation of adamantane.[1] It is a precursor to several adamantane derivatives.[2]
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.[3] [4][5]
References
- ↑ Geluk, H. W.; Keizer, V. G. (1973). "Adamantanone". Organic Syntheses 53: 8. doi:10.15227/orgsyn.053.0008.
- ↑ Fleming, Michael P.; McMurry, John E. (1981). "Reductive Coupling of Carbonyls to Alkenes: Adamantylideneadamantane". Organic Syntheses 60: 113. doi:10.15227/orgsyn.060.0113.
- ↑ 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.
- ↑ 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.
- ↑ Stothers, J.B.; Tan, C.T. (1974). "Adamantanone: stereochemistry of its homoenolization as shown by 2H nuclear magnetic resonance". Journal of the Chemical Society, Chemical Communications (18): 378–379. doi:10.1039/C39740000738.
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