Norcamphor

Last updated
Norcamphor
Norcamphor.svg
Names
IUPAC name
Bicyclo[2.2.1]heptan-2-one
Other names
2-Norbornanone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.134 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/C7H10O/c8-7-4-5-1-2-6(7)3-5/h5-6H,1-4H2
    Key: KPMKEVXVVHNIEY-UHFFFAOYSA-N
  • InChI=1/C7H10O/c8-7-4-5-1-2-6(7)3-5/h5-6H,1-4H2
    Key: KPMKEVXVVHNIEY-UHFFFAOYAC
  • O=C1CC2CC1CC2
Properties
C7H10O
Molar mass 110.156 g·mol−1
AppearanceColorless 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).

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.

Contents

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]

See also

References

  1. 1 2 "Norcamphor". Sigma-Aldrich . Retrieved March 11, 2013.
  2. ↑ Kleinfelter, Donald C.; Schleyer, Paul von R. (1962). "2-Norbornanone". Org. Synth. 42: 79. doi:10.15227/orgsyn.042.0079.
  3. ↑ 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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