89229-73-2

Upstream product

• 80706-71-4 benzoyl-2 methyl-2 cyclobutanone 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 

Downstream Products

• 51975-22-5 5-methyl-6-phenyl-3,4-dihydro-2H-pyran-2-one 
• 85237-67-8 3-Methyl-2-phenyl-piperidin 

Relevant academic research and scientific papers

A new set of nickelacyclic carboxylates ( nickelalactones ) containing pyridine as supporting ligand: Synthesis, structures and application in C-C- and C-S- linkage reactions

Nickelacycles of the type [(py)2Ni(CH2 COO)](1a), [(py) 2Ni(C(Et) C(Et)=COO)] (2a), and [(py)Ni (CH2)-CH2-COO)] (3a) were synthesized and structurally investigated by NMR, IR spectroscopy and in case of 1a and 2a by X-ray diffraction analysis. In 1a and 2a the Ni(II) ion has square-planar geometry, in contrast to the η3 allyl compound [(bipy)Ni(CH2)-CH2-COO)] (3b), in which nickel center adopts square-pyramidal geometry. 1a reacts with di(2-pyridyl)dimethylsilane (Me2(2-py)2Si) under exchange of the pyridine ligands to give 1c. 1a-3a and their bipy derivatives react with di-p-tolyldisulfide to form β-thioesters upon workup. Furthermore, reaction of 2-bromopropiophenone with nickelacycles of the type 2 results in the formation of 3,4-diethyl-6-hydroxy-5-methyl-6-phenyl-5,6-dihydro-2H-pyrane-2-one in good yields (64-75%). These reactions offer attractive new preparative routes for functionalized organic compounds.

Iodine(III)-Mediated Contraction of 3,4-Dihydropyranones: Access to Polysubstituted γ-Butyrolactones

Functionalized γ-butyrolactones are privileged structures in the field of medicinal chemistry; they are found in numerous natural products and synthetic compounds with diverse biological activities. The oxidative ring contraction of 3,4-dihydropyran-2-one derivatives represents a promising yet underappreciated strategy to access these compounds. To the best of our knowledge, very few examples of this strategy have been reported, with limited investigation of the influence of stereogenic centers on the starting dihydropyranones. We investigated the iodine(III)-mediated contraction of a representative set of dihydropyranone derivatives. The method gives rapid access to functionalized γ-butyrolactones in good yields. The reaction scope was investigated, and the method was found to support various levels of substituents, even enabling access to sterically congested quaternary centers. The stereoselectivity was investigated using chiral substrates and a chiral iodine(III) reagent.

ETUDE DES PETITS CYCLES-XLIV. UNE VOIE DE SYNTHESE DES ACYL-2 CYCLOBUTANONES

Organic peracid oxidation of α-cyclopropylidene ketones and acetals substituted in the vinylic position leads to the corresponding oxaspiropentyl ketones and acetals.Esters are also formed from the products of the Baeyer-Villiger oxidation; they are easily removed from the crude product.Unsubstituted oxaspiropentyl ketones are not obtained by this method; they are obtained by oxidation of oxaspiropentyl alcohols ( formed by epoxidation of α-cyclopropylidene alcohols).The isomerisation, either spontaneous or through reaction with lithium halides, of oxaspiropentyl ketones and acetals, gives 2-acyl-cyclobutanones and corresponding mono-acetals.These new unstable 1,3-diones must be stored in CCl4 solution.They are present in the dione form only.They add water and methanol, in acidic and even in neutral medium, leading to ring opening products. 2-Benzoyl cyclobutanone 4g is easily rearranged into 3,4-dihydro-6-phenyl 2-pyrone 12.Deacetalization of the 2-acyl-cyclobutanones mono-acetals 7B-11b into the corresponding diones is not possible even by the moist silicagel technique.

2-ACYLCYCLOBUTANONES FROM α-CYCLOPROPYLIDENE KETONES

Oxaspiropentyl ketones and acetals prepared from α-cyclopropylidene ketones and acetals undergo, with lithium halides, isomerisation to 2-acylcyclobutanones and monoacetals.