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α-tropolone
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Tropolone is an organic compound with the chemical formula . It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor. Although not usually prepared from tropone, it can be viewed as its derivative with a hydroxyl group in the 2-position.
Chemical data
- Formula
- C7H6O2
- Molecular weight
- 122.12 g/mol
- IUPAC name
- 2-hydroxycyclohepta-2,4,6-trien-1-one
- SMILES
- C1=CC=C(C(=O)C=C1)O
- InChIKey
- MDYOLVRUBBJPFM-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
4 papers- Enhancing Flavins Photochemical Activity in Hydrogen Atom Abstraction and Triplet Sensitization through Ring-Contraction.Angewandte Chemie (International ed. in English) · 2024
- Regulation of the frontier molecular orbitals and photophysical properties of boron tropolonate complexes by regioselective functionalization.Chemical communications (Cambridge, England) · 2025
- Occupational exposure to organotin substances: Development of a liquid chromatographic separation method for 11 organotin compounds in workplace air samples via HPLC-ICP-MS.Journal of chromatography. A · 2024
- The discovery of a novel route to highly substituted α-tropolones enables expedient entry to the core of the gukulenins.Organic letters · 2015
via PubMed
Wikidata facts
- Mass
- 122.037
Show 4 more facts
- chemical formula
- C₇H₆O₂
- canonical SMILES
- C1=CC=C(C(=O)C=C1)O
- melting point
- 53
- Commons category
- Tropolone
via Wikidata · CC0
~6 min read
Encyclopedic overview
4 sectionsContents
- Synthesis and reactions
- Natural occurrence
- Tropolone derivatives
- References
Tropolone is an organic compound with the chemical formula . It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor. Although not usually prepared from tropone, it can be viewed as its derivative with a hydroxyl group in the 2-position.
==Synthesis and reactions== Many methods have been described for the synthesis of tropolone. One involves bromination of 1,2-cycloheptanedione with N-bromosuccinimide followed by dehydrohalogenation at elevated temperatures, while another uses acyloin condensation of the ethyl ester of pimelic acid the acyloin again followed by oxidation by bromine. class=skin-invert-image|500px
Excerpted from Wikipedia’s “α-tropolone” article, available under the CC BY-SA 4.0 licence.