Norcamphor
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| Names | |
|---|---|
| IUPAC name
Bicyclo[2.2.1]heptan-2-one | |
| Other names
2-Norbornanone | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.134 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C7H10O | |
| Molar mass | 110.156 g·mol−1 |
| Appearance | Colorless solid |
| Melting point | 93 to 96 °C (199 to 205 °F; 366 to 369 K)[1] |
| Boiling point | 168 to 172 °C (334 to 342 °F; 441 to 445 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Norcamphor is an organic compound, classified as a bicyclic ketone. It is an analog of camphor, but without the three methyl groups. A colorless solid, it is used as a building block in organic synthesis.
Synthesis and reactions
[edit]Norcamphor was prepared from a Diels-alder reaction of cyclopentadiene and vinyl acetate, followed by oxidation with chromic acid in acetic acid solution. A more recent synthesis produces norbornene via the 2-formate ester, oxidized with chromic acid in acetone. It is a precursor to norborneols.[2] The enzymatically mediated Baeyer-Villiger oxidation of norcamphor gives the lactone.[3]
See also
[edit]References
[edit]- 1 2 "Norcamphor". Sigma-Aldrich. Retrieved March 11, 2013.
- ↑ Kleinfelter, Donald C.; Schleyer, Paul von R. (1962). "2-Norbornanone". Org. Synth. 42: 79. doi:10.15227/orgsyn.042.0079.
- ↑ Leisch, Hannes; Morley, Krista; Lau, Peter C. K. (2011). "Baeyer−Villiger Monooxygenases: More Than Just Green Chemistry". Chemical Reviews. 111 (7): 4165–4222. doi:10.1021/cr1003437. PMID 21542563.
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