Tropone

Tropone[1]
Structure of tropone
Structure of tropone
Space-filling model of tropone
Space-filling model of tropone
Names
Preferred IUPAC name
Cyclohepta-2,4,6-trien-1-one
Other names
Cyclohepta-2,4,6-trienone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.933 Edit this at Wikidata
UNII
  • InChI=1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H checkY
    Key: QVWDCTQRORVHHT-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H
    Key: QVWDCTQRORVHHT-UHFFFAOYAM
  • O=C\1/C=C\C=C/C=C/1
Properties
C7H6O
Molar mass 106.12 g/mol
Density 1.094 g/mL
Boiling point 113 °C (235 °F; 386 K) (15 mmHg)
Hazards
Flash point > 113 °C (235 °F; 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Tropone or 2,4,6-cycloheptatrien-1-one is an organic compound with some importance in organic chemistry as a non-benzenoid aromatic.[2] The compound consists of a ring of seven carbon atoms with three conjugated alkene groups and a ketone group. The related compound tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one) has an additional alcohol (or an enol including the double bond) group next to the ketone. Tropones are uncommon in natural products, with the notable exception of the 2-hydroxyl derivatives, which are called tropolones.

Tropone has been known since 1951 and is also called cycloheptatrienylium oxide. The name tropolone was coined by M. J. S. Dewar in 1945 in connection to perceived aromatic properties.[3]

  1. ^ Tropone at Sigma-Aldrich
  2. ^ Pauson, Peter L. (1955). "Tropones and Tropolones". Chem. Rev. 55 (1): 9–136. doi:10.1021/cr50001a002.
  3. ^ M. J. S. Dewar (1945). "Structure of Stipitatic Acid". Nature. 155 (3924): 50–51. Bibcode:1945Natur.155...50D. doi:10.1038/155050b0. S2CID 4086209.