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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
208-725-6
Beilstein/REAXYS Number:
1902335
MDL number:
Assay:
97%
Form:
liquid
InChI key
QVWDCTQRORVHHT-UHFFFAOYSA-N
InChI
1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H
SMILES string
O=C1C=CC=CC=C1
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
Quality Level
Related Categories
General description
Metal-catalyzed [6+3] cycloaddition of tropone with azomethine ylides has been reported.
Application
Tropone has been used in synthesis of:
- bicyclic δ-lactones via heterocyclic carbine-catalyzed [8+3] annulation pathway
- 6,7-benzobicyclo [3.2.2] nona-3,6,8-trien-2-one via thermal addition to bezyne
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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Y Nakagawa et al.
Chemico-biological interactions, 116(1-2), 45-60 (1999-01-07)
The mechanism of mitochondrial dysfunction and toxicity induced by the tropolones, beta-thujaplicin (4-isopropyl tropolone), tropolone and tropone, has been studied in freshly isolated rat hepatocytes. Incubation of hepatocytes with beta-thujaplicin (1-4 mM) elicited a concentration and time-dependent cell killing. The
K P Randau et al.
Die Pharmazie, 64(5), 350-351 (2009-06-18)
Two tropone derivatives, orobanone (1), previously isolated from Orobanche rapum-genistae, and the new natural product pernambucone (3,8-dimethyl-5-isopropyl-2,3-dihydro-1H-azulene-1,6-dione, 2), were isolated from the sterm bark of Croton argyroglossum. The structures were elucidated from spectroscopic data.
Vijay Nair et al.
The Journal of organic chemistry, 71(23), 8964-8965 (2006-11-04)
A novel protocol for the annulation of tropone to enals involving nucleophilic heterocyclic carbene (NHC) catalyzed homoenolate formation has been developed. Interestingly, the reaction led to bicyclic delta-lactones instead of the expected gamma-spirolactones, presumably by the uncommon [8 + 3]
L Isakovic et al.
Organic letters, 3(26), 4189-4192 (2002-01-11)
The carbocyclic core of CP-225,917 and CP-263,114 is accessible through the [6+4] cycloaddition of a tropone with a 2-substituted cyclopentadiene. Examination of this reaction has revealed for the first time that this cycloaddition process is catalyzed by Lewis acids, including
Barry M Trost et al.
Journal of the American Chemical Society, 130(45), 14960-14961 (2008-10-22)
The cyanosubstituted trimethylenemethane donor undergoes palladium-catalyzed [6 + 3] cycloaddition with a variety of tropones to yield bicyclo[4.3.1]decadienes in excellent regio-, diastereo-, and enantioselectivity. Products of the Pd-TMM [6 + 3] cycloaddition participate in a thermal [3,3] sigmatropic rearrangement to
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