27655-70-5

Basic information

• Product Name: Bicyclo[4.2.0]octan-7-one, (1R,6R)-rel-
• CAS NO: 27655-70-5
• Molecular Formula: C8H12O
• Molecular Weight: 124.183
• Mol File: 27655-70-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Bicyclo[4.2.0]octan-7-one, (1R,6R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[4.2.0]octan-7-one, (1R,6R)-rel-(27655-70-5)
• EPA Substance Registry System: Bicyclo[4.2.0]octan-7-one, (1R,6R)-rel-(27655-70-5)

Safety Data

• Hazardous Substances Data: 27655-70-5(Hazardous Substances Data)

Upstream product

• 286-08-8 bicyclo[4.1.0]heptane 
• 201230-82-2 carbon monoxide 
• 74897-66-8 2-cyclohexylacetyltetrazole 
• 74897-64-6 1-cyclohexylacetyl-1,2,4-triazole 
• 82031-98-9 1,1,2,2,3,3,4,4,4-Nonafluoro-butane-1-sulfonic acid (1R,2S)-2-ethynyl-cyclohexyl ester 
• 82031-85-4 2-Ethinylcyclohexyl-<4-(dimethylamino)benzolsulfonat> 
• 75-89-8 2,2,2-trifluoroethanol 
• 127-19-5 N,N-dimethyl acetamide 
• 110-83-8 cyclohexene 
• 69393-32-4 2-(7'-Hydroxybicyclo<4.2.0>oct-7'-yl)-imidazol 
• 31996-68-6 bicyclo[4.2.0]-oct-2-en-7-one 
• 97487-09-7 bicyclo<4.2.0>oct-1(8)-en-8-yl nonaflate 
• 32166-29-3 8,8-dichlorobicyclo[4.2.0]octan-7-one 

Downstream Products

• 61469-56-5 2-(2-Oxo-hexyl)-cyclohexanone 
• 43119-27-3 (3aR,7aR)-hexahydrobenzofuran-2(3H)-one 
• 74708-16-0 (3aS,7aS)-hexahydrobenzofuran-2(3H)-one 
• 65376-02-5 (1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one 
• 89395-29-9 (3aR,7aS)-hexahydroisobenzofuran-1-one 
• 41894-93-3 hexahydro-indan-2-one 
• 29927-85-3 hexahydro-indan-1-one 

Relevant articles and documents

Transition-Metal-Free Access to Heteroaromatic-Fused 4-Tetralones by the Oxidative Ring Expansion of the Cyclobutanol Moiety

Advances in the transition-metal-free cyclobutanol ring expansion to 4-tetralones under N-bromosuccinimide mediation are described. We have expanded the scope of this ring expansion methodology and investigated the effect substituents on the aromatic ring, and the cyclobutanol moiety, have on the outcome of the reaction. Limitations with certain substituents on the cyclobutanol moiety are also described. Further experimental evidence to support our mechanistic understanding is disclosed, and we now preclude the suggested involvement of a primary radical for this transformation.

Baeyer-Villiger Oxidation of Cyclobutanones with 10-Methylacridinium as an Efficient Organocatalyst

Baeyer-Villiger oxidation of cyclobutanones is achieved in current developed protocol with 10-methylacridinium perchlorate (AcrH +ClO4-) as a novel organocatalyst both with irradiation at room temperature and without irradiation at elevated temperature. Excellent yields of the corresponding lactones are obtained and the possible mechanism has been proposed.

Enolate Reactions of Bicyclooctan-7-ones

Under kinetic conditions, the lithium enolate formed from the bicyclooctan-7-one 3 undergoes reaction with MeI, EtI, and dimethyl disulfide to give 6-substituted compounds 7-9 in 65percent, 43percent, and 70percent yield, respectively, rather than the anticipated 8-substituted isomers.Similarly, fluorination of the silyl enol ether gives the 6-fluoro compound 10 in 40percent yield.Using a TMSCl trapping technique it was shown that kinetic deprotonation takes place at both the 6- and 8-positions in bicyclooctan-7-ones, whereas the thermodynamic product is the expected 6-enolate.Generation of the enolate from a mixture of 6- and 7-silyl enol ethers (57:43) results in 6- and 8-alkylated products.The kinetic enolate from bicyclooct-2-en-7-one is the 7-enol derivative.