cyclohepta-2,4,6-trien-1-one

• ChemBase ID: 130046
• Molecular Formular: C7H6O
• Molecular Mass: 106.12194
• Monoisotopic Mass: 106.04186481
• SMILES: O=c1cccccc1
• Canonical SMILES: O=c1cccccc1
• InChI: InChI=1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H
• InChIKey: QVWDCTQRORVHHT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclohepta-2,4,6-trien-1-one
• IUPAC Traditional name: tropone
• Synonyms: 2,4,6-Cycloheptatrien-1-one; Tropone; Tropone; Cycloheptatrienone; 2,4,6-环庚三烯-1-酮; 环庚三烯酮

Database IDs

• CAS Number: 539-80-0
• EC Number: 208-725-6
• MDL Number: MFCD00014331
• Beilstein Number: 1902335
• PubChem SID: 24855242; 162224331
• PubChem CID: 10881
• Chemspider ID: 10419
• Wikipedia Title: Tropone

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.3343216
• LogD (pH = 7.4): 1.3343216
• Log P: 1.3343216
• Molar Refractivity: 36.1516 cm^3
• Polarizability: 12.250373 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 113 °C (15 mmHg); 113 °C/15 mmHg(lit.); 91-92°C/4mm
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F
• Density: 1.094; 1.094 g/mL; 1.094 g/mL at 25 °C(lit.)
• Refractive Index: 1.6150; n20/D 1.615(lit.)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C7H6O

DETAILS

Sigma Aldrich - 252832

Packaging
1, 5 g in glass bottle

REFERENCES

• Reacts as a diene in the Diels-Alder reaction with electron-rich alkenes (inverse electron-demand); see, e.g.: Org. Synth. Coll., 9, 396 (1998):
  
• Alternatively, reaction can occur with electron-deficient alkenes, as exemplified by phenyl vinyl sulfoxide. In this case, cyclic elimination leads directly to bicyclo[3.2.2]nona-3,6,8-trien-2-one in low yield: J. Org. Chem., 48, 3591 (1983). For a review of cycloadducts of tropone and its analogs with sulfenes and ketenes, see: Heterocycles, 18, 343 (1982).
• For cycloaddition reactions with kinetically stabilized phosphaalkynes, leading to tetracyclic phosphorus-carbon cage compounds, see: J. Org. Chem., 60, 5884 (1995); Synthesis, 87 (1996).
• Reacts with Grignard reagents at the 2-position (1,6-addition) as in the first step of a synthesis of the hydroazulene skeleton: Tetrahedron Lett., 23, 1863 (1982). Addition of various Li enolates again leads to 2-substituted 2,6-dihydrotropones in good yield: J. Org. Chem., 53, 4596 (1988).