252832

Sigma-Aldrich

Tropone

97%

Synonym(s):
2,4,6-Cycloheptatrien-1-one
Empirical Formula (Hill Notation):
C7H6O
CAS Number:
Molecular Weight:
106.12
Beilstein/REAXYS Number:
1902335
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

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

Looking for similar products? Visit Product Comparison Guide

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

Packaging

1, 5 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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.
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...
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...
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...
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]...

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.