5670-51-9

Usage

Type of compound

Cyclic ketone

Presence of functional groups

Nitrile group

Versatility in organic synthesis

Acts as a valuable intermediate

Common uses

Preparation of pharmaceuticals and agrochemicals

Chemical reactivity

Ability to undergo various chemical reactions and form diverse functional groups

Applications

Production of fine chemicals, dyes, and specialty chemicals

Potential use in materials science

Synthesis of complex organic molecules

Upstream product

• 4513-77-3 2-cyanocyclohexanone 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 
• 646-20-8 pimelonitrile 
• 15595-71-8 2-aminocyclohex-1-enecarbonitrile 
• 822-87-7 2-Chlorocyclohexanone 
• 152297-24-0 (S)-2-[(E)-(S)-2-Methoxymethyl-pyrrolidin-1-ylimino]-1-methyl-cyclohexanecarbonitrile 
• 406909-97-5 (1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile 

Downstream Products

• 50744-44-0 (Z)-6-Cyano-5-heptenal 
• 50744-43-9 (E)-6-Cyano-5-heptenal 
• 1206-21-9 2-benzyl-2-methyl-cyclohexanone 
• 16178-87-3 2-methyl-2-allylcyclohexanone 
• 1032593-02-4 C₁₄H₁₅NS 
• 406909-97-5 (1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile 
• 406909-98-6 (1S,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile 
• 66984-23-4 (+/-)-(1R,2S)-1-methyl-2-hydroxy-1-cyclohexanecarbonitrile 
• 66984-23-4 2-hydroxy-1-methylcyclohexanecarbonitrile 

Relevant academic research and scientific papers

Synthesis and Enzymatic Kinetic Resolution of α,α -Disubstituted Cyclic Hydroxy Nitriles

Herein, we describe the diastereoselective synthesis of five- and six-membered α,α-disubstituted cyclic β-hydroxy nitriles and their resolution via enzymatic transesterification. By this method, all possible stereoisomers were obtained in enantiopure form and high yield.

Preparation of enantiopure ketones and alcohols containing a quaternary stereocenter through parallel kinetic resolution of β-keto nitriles

Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kineticresolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.

Lithium naphthalenide induced reductive alkylation of α-cyano ketones. A general method for regiocontrol of α,α-dialkylation of ketones

An efficient general method for the consecutive introduction of two alkyl groups to the α carbon of a ketone carbonyl has been developed, making use of the lithium naphthalenide induced reductive alkylation of an α-cyano ketone system as a key operation.

Enantioselective synthesis of 2-alkyl-2-cyanocycloalkanones with a quaternary stereogenic center

2-Alkyl-2-cyanocycloalkanones 4 bearing a quaternary stereogenic center are synthesized in good overall yields and high enantiomeric excesses (ee = 90-95%) employing the SAMP-/RAMP-hydrazone method. The absolute configuration is confirmed by NMR-spectroscopic investigations on SAMP-hydrazone 3a and an X-ray structure analysis of SAMP-hydrazone 3f.