32561-55-0

Upstream product

• 124015-87-8 2-methyl-1,3-cyclohexanedione-dimethylhydrazone 
• 504-02-9 1,3-cylohexanedione 
• 69948-55-6 3-(2,2-dimethylhydrazino)cyclohex-2-en-1-one 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 106-96-7 propargyl bromide 

Downstream Products

• 32561-57-2 2-Methyl-2-(2-oxopropyl)-1,3-cyclohexanedione 
• 90130-94-2 (2R,3S)-(+)-3-hydroxy-2-methyl-2-(2-propynyl)cyclohexan-1-one 
• 90105-52-5 (2S,3S)-(+)-3-hydroxy-2-methyl-2-(2-propynyl)cyclohexan-1-one 
• 90130-93-1 (2R,3R)-3-Hydroxy-2-methyl-2-prop-2-ynyl-cyclohexanone 
• 90130-95-3 (2S,3R)-3-Hydroxy-2-methyl-2-prop-2-ynyl-cyclohexanone 
• 90105-52-5 rac-(2S,3S)-3-hydroxy-2-methyl-2-(prop-2-yn-1-yl)cyclohexan-1-one 
• 90105-52-5 rac-(2S,3R)-3-hydroxy-2-methyl-2-(prop-2-yn-1-yl)cyclohexan-1-one 
• 1637438-98-2 2-[3-(4-chlorophenyl)prop-2-yn-1-yl]-2-methylcyclohexane-1,3-dione 
• 1637438-97-1 2-[3-(4-methoxyphenyl)prop-2-yn-1-yl]-2-methylcyclohexane-1,3-dione 
• 1637438-96-0 2-methyl-2-(3-phenylprop-2-yn-1-yl)cyclohexane-1,3-dione 
• 1353094-21-9 3-methyl-3-propargylcyclohex-5-en-1,2,4-trione 

Relevant academic research and scientific papers

Fsp3-rich and diverse fragments inspired by natural products as a collection to enhance fragment-based drug discovery

Herein, we describe the natural product inspired synthesis of 38 complex small molecules based upon 20 unique frameworks suitable for fragment-based screening. Utilising an efficient strategy, two key building block diastereomers were harnessed to generate novel, three-dimensional fragments which each possess numerous synthetically accessible fragment growth positions.

Construction of 1-Tetralols Bearing Two Contiguous Quaternary Chiral Centers through a Rhodium-Catalyzed Enantioselective Desymmetrization Cascade Reaction

A novel and efficient access to polyfunctionnalized chiral 1-tetralols, bearing two contiguous quaternary carbon stereocenters, has been developed from various and easily accessible alkynyl-1,3-diketones, through a cascade process including a regioselective alkyne insertion, a 1,4-Rh shift, and a nucleophilic addition step via the desymmetrization of the 1,3-diketone moiety thanks to an appropriate rhodium-chiral diene complex in the presence of arylboronic acids.

Desymmetric enantioselective reduction of cyclic 1,3-diketones catalyzed by a recyclable p-chiral phosphinamide organocatalyst

The P-stereogenic phosphinamides are a structurally novel skeletal class which has not been investigated as chiral organocatalysts. However, chiral cyclic 3-hydroxy ketones are widely used as building blocks in the synthesis of natural products and bioactive compounds. However, general and practical methods for the synthesis of such chiral compounds remain underdeveloped. Herein, we demonstrate that the P-stereogenic phosphinamides are powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol displays a broad substrate scope that is amenable to a series of cyclic 2,2-disubstituted five- and six-membered 1,3-diketones. The chiral cyclic 3-hydroxy ketone products bearing an all-carbon chiral quaternary center could be obtained with high enantioselectivities (up to 98% ee) and diastereoselectivities (up to 99:1 dr). Most importantly, the reactions could be practically performed on the gram scale and the catalysts could be reused without compromising the catalytic efficiency. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species. The results disclosed herein bode well for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.

2,2′-Isopropylidenebis[(4S,5R)-4,5-di(2-naphthyl)-2-oxazoline] ligand for asymmetric cyclization-carbonylation of meso-2-alkyl-2-propargylcyclohexane-1,3-diols

The oxidative cyclization-carbonylation of meso-2-alkyl-2-propargylcyclohexane-1,3-diols mediated by Pd(II) with chiral bisoxazoline (box ligand) afforded bicyclic-β-alkoxyacrylates. Based on a ligand screening, 2,2′-isopropylidenebis[(4S,5R)-4,5-di(2-nap

An NMR tool for cyclodextrin selection in enantiomeric resolution by high-performance liquid chromatography

Complexation-induced chemical shifts and diffusion coefficients (HR-DOSY) of enantiomers with native and derivatized cyclodextrins were used for calculations of the apparent binding constants of three cyclohexanone inclusion complexes. Correlations between these data and high-performance liquid chromatography were established, revealing that this approach can be applied as an alternative method to predict enantiomeric discrimination. Copyright

Diastereoselective synthesis of a seco-taxane

Ketone 9 was synthesized in 7 steps from commercially available 2- methylcyclohexane-1,3-dione in a diastereoselective fashion. Shapiro reaction of easily available trisylhydrazone 11 with benzaldehyde was used as a model for A- and C-ring coupling. Final

Regioselective alkylations of cyclic 1,3-diketones via metalated dimethylhydrazones

Cyclic 1,3- diketones 1 are transformed into their 2,2-dimethylhydrazones 2, which can be alkylated regioselectively at different positions after mono-, di-, tri-, and tetrametalation. Monometalated C-2 unsubstituted hydrazones afford C-2 and N- alkylation, monometalated C-2 substituted hydrazones afford only C-2 alkylation.The regioselectivity of the alkylation of the polymetalated hydrazones follows Hauser's rule according to the sequence: NH- > C-4 Ha > C-5 > C-4 Hb. Hydrolysis of the product hydrazones 3-5 afforded mono- and polyalkylated 1,3- diketones 7 in good yields.

Asymmetric Microbial Reduction of Prochiral 2,2-Disubstituted Cycloalkanediones

Asymmetric microbial reduction of a series of 2,2-disubstituted 1,3-cycloalkanediones with bakers' yeast was examined as an example of an enzyme-catalyzed distinction of a substrate containing two trigonal carbonyl centers with stereoheterotropic faces an

CHIRAL CYCLOHEXANOID SYNTHETIC PRECURSORS VIA ASYMMETRIC MICROBIAL REDUCTION OF PROCHIRAL CYCLOHEXANEDIONES

Microbial reduction of various 2,2-disubstituted-1,3-cyclohexanediones with bakers' yeast provides efficient access to chiral cyclohexanoid synthetic precursors.