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252832

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

Quality Level

100

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

252832-1G:
252832-5G:
252832-VAR:
252832-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ2415
MKCJ3829
MKCG2447
MKCC2486
MKBV4204V

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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
Barry M Trost et al.
Organic letters, 11(16), 3782-3785 (2009-07-18)
A concise approach to the core skeleton of the welwitindolinone alkaloids was developed on the basis of sequential cycloaddition reactions. First, a palladium catalyzed enantioselective [6 + 3] trimethylenemethane cycloaddition onto a tropone nucleus was used to generate the requisite
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.
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
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
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