114145-16-3

Upstream product

• 28046-90-4 4-bromo-1-methylcyclohexane 
• 105-56-6 ethyl 2-cyanoacetate 
• 57093-77-3 cyano-(4-methyl-cyclohexylidene)-acetic acid ethyl ester 
• 589-92-4 1-methylcyclohexan-4-one 

Downstream Products

• 6603-71-0 4-methylcyclohexyl acetic acid 
• 855417-96-8 Methyl-4-cyclohexyl-cyanessigsaeure 
• 344307-37-5 Methyl-4-cyclohexylessigsaeure-methylester 
• 57093-76-2 Methyl cis-4-methylcyclohexaneacetate 
• 57093-75-1 Methyl trans-4-methylcyclohexaneacetate 

Relevant academic research and scientific papers

Development of drug intermediates by using direct organocatalytic multi-component reactions

Development of drug intermediates by using direct amino acid organocatalytic multi-component reaction was investigated. Hydrogenations of double-bond containing compounds including carbonyls, imines and olefins are important for living organisms as well as for the industrial production of chemicals. Amino acid catalysis has emerged as a powerful green synthetic tool for the development of both achiral and chiral catalysis of condensations and cycloadditions and the 1,2- and 1,4-additions of enals, enones and ketones including electrophiles. It was found that the amino acid proline 4a catalyzes the Knoevenagel condenstion of cyclohexanone 1a with the CH-acid ethyl cyanoacetate 2a to furnish the active olefin 9aa. This simple and environmentally friendly approach can be used to construct highly substituted hydrogenated products in a regioselective fashion with good yields.

Stereochemistry of 1,4-Addition of Nucleophiles to Ethyl Cyclohexylidenecyanoacetates

The stereochemistry of 1,4-addition of several nucleophiles such as cyanide, sodium borohydride, and methylmagnesium iodide to three substituted ethyl cyclohexylidenecyanoacetates (1-3) has been determined.A higher preference for equatorial attack is observed in these compounds than in related cyclohexanones, which is considerably diminished by the use of aprotic polar solvents.The results do not show any appreciable contribution of product stability control, recently shown to be important for hydride reduction of cyclohexanones, and have been rationalized on thebasis of a six-center cyclic transition state in which steric factors play a dominant role.These compounds have also been reduced by catalytic hydrogenation (Pd/C), and, interestingly, with unhindered systems (1, 2) hydrogenation takes place more from the axial side (40-60percent) as compared to cyclohexanones.