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539-80-0 molecular structure
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cyclohepta-2,4,6-trien-1-one

ChemBase ID: 130046
Molecular Formular: C7H6O
Molecular Mass: 106.12194
Monoisotopic Mass: 106.04186481
SMILES and InChIs

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

Cite this record

CBID:130046 http://www.chembase.cn/molecule-130046.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.3343216  LogD (pH = 7.4) 1.3343216 
Log P 1.3343216  Molar Refractivity 36.1516 cm3
Polarizability 12.250373 Å3 Polar Surface Area 17.07 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Boiling Point
113 °C (15 mmHg) expand Show data source
113 °C/15 mmHg(lit.) expand Show data source
91-92°C/4mm expand Show data source
Flash Point
>110°C(230°F) expand Show data source
>113 °C expand Show data source
>235.4 °F expand Show data source
Density
1.094 expand Show data source
1.094 g/mL expand Show data source
1.094 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.6150 expand Show data source
n20/D 1.615(lit.) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
97% expand Show data source
Empirical Formula (Hill Notation)
C7H6O expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 252832 external link
Packaging
1, 5 g in glass bottle

REFERENCES

REFERENCES

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  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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