Norcamphor
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| 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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Synthesis and reactions
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]
