27655-70-5

Upstream product

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

Downstream Products

• 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 
• 1196-52-7 7-Methyl-cis-7-azabicyclo<4.3.0>nonan-8-one 
• 125260-21-1 3,5-Dinitro-benzoic acid (1S,6S,7S)-7-vinyl-bicyclo[4.2.0]oct-7-yl ester 
• 125260-21-1 3,5-Dinitro-benzoic acid (1R,6R,7S)-7-vinyl-bicyclo[4.2.0]oct-7-yl ester 
• 125260-14-2 Benzoic acid (1S,6S,7S)-7-vinyl-bicyclo[4.2.0]oct-7-yl ester 
• 61469-56-5 2-(2-Oxo-hexyl)-cyclohexanone 

Relevant academic research and scientific papers

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.

Direct syntheses of spiro- and fused-hydrofurans by a tunable tandem semipinacol rearrangement/oxa-michael addition protocol

A highly chemoselective one-pot reaction has been developed involving a tandem semipinacol rearrangement/oxa-Michael addition sequence in which the in situ generated ketol diene intermediate can be transformed specifically to either the spiro- or fused-dihydrofuran products (see scheme). This one-pot tandem reaction represents a general synthetic methodology for the syntheses of the two different kinds of furan derivatives. Copyright

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.

Bicyclic nucleoside synthesis - A photochemical approach

The synthesis of a series of bicyclic nucleosides using photolytic ring-expansion of cyclobutanones is reported. The cyclobutanone precursors were prepared by [2+2] cycloaddition of a series of cyclic alkenes with chlorinated ketenes, derived from dichloro- and trichloroacetyl chloride. The synthesis of the nucleosides was achieved through photolysis of cyclobutanone precursors with 6-chloropurine by UV irradiation. The generality of this method was investigated and the absolute stereochemistry was assigned by NMR spectroscopy. The photoproducts demonstrated a marked preference for the 2′-exo conformation. Copyright Taylor & Francis Group, LLC.

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.

Vinyl Cations, 37. Rearrangement of Cyclic Homopropargyl Sulfonates to Condensed Cyclobutanones and Cyclopropyl Ketones

Cyclic homopropargyl sulfonates 8 (tosylates, triflates, nonaflates, and damsylates) are prepared and solvolysed.The resulting rearrangement reactions are studied with respect to the properties of the solvents used, leaving groups, the substituent on the triple bond, and with respect to the ring size of the sulfonates 8.

RHODIUM CATALYZED CARBONYLATION REACTIONS OF CYCLOPROPANES

Cyclopropane was carbonylated by 2 under carbon monoxide pressure to give cyclobutanone, dipropyl ketone, propyl isopropyl ketone, and 2- or 3-methylcyclohexanone.Some other cyclopropane derivatives were also examined.Norcarane gave a small amount of bicycloocta-7-one, though phenylcyclopropane did not give any carbonylation products.The formation of polyketone was efficient in the case of methylenecyclopropane.

PHOTOCHEMISTRY OF N-ACYLAZOLES. VI). PHOTOREACTIVITIES OF 1-ACYL-1,2,4-TRIAZOLES AND OF 2-ACYLTETRAZOLES

Contrary to the findings in the photolysis of N-acylimidazoles (2) irradiation of 1-acyl-1,2,4-triazoles afforded no photo-Fries product, but instead products formed via the corresponding acyl radicals and aldehydes.Photolysis of 2-acyltetrazoles gave in part the same products as those obtained from the irradiation of the corresponding acyl-triazoles as well as 2-alkyl-1,3,4-oxadiazoles.N-Acyltetrazoles didn't give any photo-Fries product neither.

Preparation of 15-deoxy-16-hydroxyprostaglandins

Analogues of PGE1 having the structural formula, STR1 in which J is R-hydroxymethylene or S-hydroxymethylene; R1 is hydrogen; R2 is hydrogen or together with R4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R3 is hydrogen or methyl, or together with R4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R4 is bicycloalkyl or bicycloalkenyl moiety having the formula: STR2 SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R4 is hydrogen or methyl or together with R2 or R3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R4 forms a cycloalkyl as defined above; and R6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. Pge1 ester analogues of the above formula, limited to the structures wherein two of R2, R3 R4 and R5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.

Syntheses and equilibria of fused bicyclic methylenecyclopropanes

Isomeric bicyclic methylenecyclopropanes, obtained from carbenoid ring contraction of bicyclic cyclobutanones, exhibit extraordinarily clean thermal equilibria which is entropy-controlled near the boundaries of Bredt's rule.