69687-19-0

Upstream product

• 854447-43-1 1-hydroxy-2-methyl-cyclohexanecarboxylic acid anilide 
• 933-35-7 2-methylcyclohexane cyanohydrin 
• 583-60-8 2-Methylcyclohexanone 
• 872280-31-4 1-benzoyloxy-2-methyl-cyclohexanecarboxylic acid anilide 
• 933-35-7 (+/-)-1-hydroxy-2c-methyl-cyclohexane-r-carbonitrile 

Downstream Products

• 583-60-8 2-Methylcyclohexanone 
• 61405-06-9 4-methyl-2-oxa-bicyclo[2.2.2]octan-3-one 
• 7077-04-5 2-methyl-1-cyclohexanecarboxylic acid 
• 113749-80-7 (+/-)-1-hydroxy-2t-methyl-cyclohexane-carboxylic acid-(1r)-methyl ester 
• 113749-80-7 (+/-)-1-hydroxy-2c-methyl-cyclohexane-carboxylic acid-(1r)-methyl ester 
• 6129-90-4 1-methyl-2-isopropyl-cyclohexanol-⁽²⁾ 
• 15582-48-6 o-1-menthene 
• 16580-23-7 1-isopropyl-2-methylcyclohexane 

Relevant academic research and scientific papers

Preparation and reactions of optically active cyanohydrins derived from 4-chlorobenzaldehyde, cyclohexanone and 2-methylcyclohexanone using the (R) hydroxynitrile lyase from Prunus amygdalus

CYANURATION of 4-chlorobenzaldehyde (1), cyclohexanone (2a) and 2-methylcyclo-hexanone (2b) yielded the racemic 2-hydroxy-2-(4-chlorophenyl) ethanenitrile (R,S)-3, cyclohexanone cyanohydrin 21a and (R,S)-2- methylcyclohexanone cyanohydrin (R,S)-21b. The same reaction can be completed by using acetone cyanohydrin (4) as a transcyanating agent. The optically active cyanohydrins (R)-3 and (R)-21b could be respectively obtained by hydrocyanation of 1 and 2b using (R)-hydroxynitrile lyase (R) PaHNL [EC 4.1.2.10] from almonds (Prunus amygdalus) as a chiral catalyst. Cyanohydrins 3 and 21 in their racemic and optically active forms undergo a number of transformations which involve either the hydroxyl group or the cyanide function. Moreover, derivatization of 3 and 21b with (S)-Naproxen chloride (S)-7 gave the respective diastereoisomers 8 and 22b. The optical activities of (R)-3 and 21b as well as their derivatives were recorded. The postulated structures of the new products were supported with compatible elementary and spectroscopic (IR, 1H NMR, 13C NMR, MS and X-ray crystallography) analyses. The antitumor activity of some selected racemic new products and their respective optically active analogues were undertaken. The structure-activity relationship (SAR) was also discussed.

Lactone Formation in Superacidic Media

The reaction of substituted 1-hydroxycyclohexanecarboxylic acids in fluorosulphuric acid has been studied.Cyclisation takes place around 0 deg C, accompanied by rearrangement in appropriate cases, yielding the thermodynamically stable lactone or mixture of lactones.An unexpected feature of these reactions is that the carboxy-substituted cyclohexyl carbocation does not undergo ring contraction, unlike the unsubstituted cyclohexyl carbocation, although the cycloheptyl system contracts to cyclohexyl.We suggest that the cyclohexyl carbocation is strongly stabilised by carboxyl substitution, as a result of through-space interaction between the carboxyl oxygen atom and the carbocation centre.