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Sigma-Aldrich

Tropone

97%

Synonym(s):

2,4,6-Cycloheptatrien-1-one

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About This Item

Empirical Formula (Hill Notation):
C7H6O
CAS Number:
539-80-0
Molecular Weight:
106.12
Beilstein:
1902335
EC Number:
208-725-6
MDL number:
MFCD00014331
UNSPSC Code:
12352100
PubChem Substance ID:
24855242
NACRES:
NA.22

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.)

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.

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
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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