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220841

Sigma-Aldrich

cis-1,5-Dimethylbicyclo[3.3.0]octane-3,7-dione

≥98%

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About This Item

Empirical Formula (Hill Notation):
C10H14O2
CAS Number:
Molecular Weight:
166.22
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

≥98%

form

solid

mp

228-230 °C (lit.)

SMILES string

C[C@]12CC(=O)C[C@@]1(C)CC(=O)C2

InChI

1S/C10H14O2/c1-9-3-7(11)5-10(9,2)6-8(12)4-9/h3-6H2,1-2H3/t9-,10+

InChI key

KGZWVKASYOPUET-AOOOYVTPSA-N

General description

Olefination of cis-1,5-dimethylbicyclo[3.3.0]octane-3,7-dione with (carbethoxyethylidene)triphenylphospharane under controlled microwave heating has been investigated. It reacts with carbon disulfide, strong base and an alkylating agent in dipolar aprotic solvents to yield racemic mixtures of 2-dialkylthio-methylene compounds.

Storage Class Code

11 - Combustible Solids

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)

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DITHIOCARBOXYLIERUNGSREAKTIONEN VON cis-BICYCLO [3.3. 0] OCTAN-3, 7-DIONEN. MOLEKUL-UND KRISTALLSTRUKTUR VON cis-2, 6-BIS (DIMETHYLTHIO-METHYLEN)-BICYCLO [3.3. 0] OCTAN-3, 7-DION.
Dolling W, et al.
Phosphorus, Sulfur, and Silicon and the Related Elements, 113(1-4), 263-274 (1996)
Microwave-assisted regioselective olefinations of cyclic mono-and di-ketones with a stabilized phosphorus ylide.
Wu J, et al.
Tetrahedron, 62(19), 4643-4650 (2006)

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