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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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
Strahil Berkov et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 59(3-4), 184-186 (2004-07-10)
The alkaloid spectra of Datura innoxia plants grown in Egypt and Bulgaria were investigated by GC-MS. Thirty-eight alkaloids were detected in the roots, leaves and fruits of the plants. Five new alkaloids for D. innoxia are reported. Alkaloid spectra of
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.
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)
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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