252832
Tropone
97%
Synonym(s):
2,4,6-Cycloheptatrien-1-one
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About This Item
Empirical Formula (Hill Notation):
C7H6O
CAS Number:
Molecular Weight:
106.12
Beilstein:
1902335
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
liquid
refractive index
n20/D 1.615 (lit.)
bp
113 °C/15 mmHg (lit.)
density
1.094 g/mL at 25 °C (lit.)
functional group
ketone
storage temp.
−20°C
SMILES string
O=C1C=CC=CC=C1
InChI
1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H
InChI key
QVWDCTQRORVHHT-UHFFFAOYSA-N
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General description
Metal-catalyzed [6+3] cycloaddition of tropone with azomethine ylides has been reported[1].
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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M Carmen Carreño et al.
Chemical communications (Cambridge, England), (8)(8), 1007-1009 (2005-02-19)
Synthesis of 4-aminotropones through a cyclization-ring expansion process occurs in a single step and with excellent yields from 4-amino-2,5-cyclohexadienones (p-quinamines) bearing a 4-sulfinyl or sulfonyl methyl group.
Young-Sun Do et al.
The Journal of organic chemistry, 74(2), 917-920 (2008-12-05)
A ring-expansion protocol that consisted of the 1,2-addition of various enolate nucleophiles to 6-trimethylsiloxy-2-cyclohexene-1-one (1) and the NaIO(4)-promoted oxidative ring opening of the resulting diols 2, followed by an intramolecular Knoevenagel condensation, furnished versatile dihydrotropones 6. Maintaining Z-configuration in the
Reaction of tropone with benzyne. Formation and photoisomerization of 6, 7-benzobicyclo [3.2. 2] nona-3, 6, 8-trien-2-one.
Ciabattoni J, et al.
Journal of the American Chemical Society, 89(11), 2778-2779 (1967)
Honglei Liu et al.
Journal of the American Chemical Society, 136(6), 2625-2629 (2014-01-24)
The first metal-catalyzed [6 + 3] cycloaddition of tropone with azomethine ylides has been developed. With the use of a chiral ferrocenylphosphine-copper(I) complex as the catalyst, the asymmetric variant of the [6 + 3] cycloaddition has also been successfully achieved.
Marie Varin et al.
The Journal of organic chemistry, 72(17), 6421-6426 (2007-07-28)
In this paper we report the rearrangement of spirocyclohexadienones into dihydrotropones in basic conditions as a new method for the preparation of seven-membered ring ketones, which are key building blocks for the synthesis of tropoloalkaloids. DFT calculations and deuterium labeling
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