137625-67-3

Basic information

• Product Name: (-)-(1R,2R,5R)-2-methyl-5-(1-methylethenyl)-3-oxocyclohexanecarbonitrile
• Synonyms: (-)-(1R,2R,5R)-2-methyl-5-(1-methylethenyl)-3-oxocyclohexanecarbonitrile
• CAS NO: 137625-67-3
• Molecular Weight: 177.246
• Mol File: 137625-67-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (-)-(1R,2R,5R)-2-methyl-5-(1-methylethenyl)-3-oxocyclohexanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1R,2R,5R)-2-methyl-5-(1-methylethenyl)-3-oxocyclohexanecarbonitrile(137625-67-3)
• EPA Substance Registry System: (-)-(1R,2R,5R)-2-methyl-5-(1-methylethenyl)-3-oxocyclohexanecarbonitrile(137625-67-3)

Safety Data

• Hazardous Substances Data: 137625-67-3(Hazardous Substances Data)

Upstream product

• 6485-40-1 (R)-Carvone 
• 151-50-8 potassium cyanide 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 332920-11-3 (5R)-5-isopropenyl-2-methyl-1-trimethyl-silanyloxy-cyclohex-2-ene-1-carbonitrile 
• 99-48-9 (4R,6R)-carveol 
• 155385-83-4 (-)-1-<(1-cyano-2-phenylethyl)amino>-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile 
• 155385-84-5 (-)-1-<(1-cyano-2-methylpropyl)amino>-2R-methyl-5R-(1-methylethenyl)-cyclohexane-1R,3R-dicarbonitrile 
• 155486-42-3 (1R,2R,3R,5R)-1-((S)-1-Cyano-2-methyl-propylamino)-5-isopropenyl-2-methyl-cyclohexane-1,3-dicarbonitrile 
• 74-90-8 hydrogen cyanide 

Downstream Products

• 1206627-33-9 (1S,2S,4R,6S)-6-aminomethyl-8-p-menthen-2-ol 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 1173162-93-0 (6R,4S)-6-cyano-p-mentha-1,8-diene 
• 1173162-91-8 (1R,2S,4R,6R)-6-cyano-8-p-menthen-2-ol 
• 1265457-22-4 (6R,4S)-6-(aminomethyl)-p-mentha-1,8-diene 
• 155385-79-8 (-)-1-amino-2R-methyl-5R-(1-methylethenyl)cyclohexane-1,3R-dicarbonitrile 
• 143023-78-3 (+)-5R-(1-Hydroxy-1-methyl ethyl)-3S-(N-acetylaminomethyl)-2-methylcyclohexanone 
• 143023-76-1 (+)-5R-(1-Hydroxy-1-methyl ethyl)-3S-(N-acryloylaminomethyl)-2-methylcyclohexanone 
• 155385-83-4 (-)-1-<(1-cyano-2-phenylethyl)amino>-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile 
• 155486-41-2 (1R,2R,3R,5R)-1-((S)-1-Cyano-2-phenyl-ethylamino)-5-isopropenyl-2-methyl-cyclohexane-1,3-dicarbonitrile 
• 155385-85-6 (-)-1S-<(cyano phenyl methyl)amino>-2R-methyl-5R-(1-methylethenyl)-cyclohexane-1R,3R-dicarbonitrile 
• 155385-84-5 (-)-1-<(1-cyano-2-methylpropyl)amino>-2R-methyl-5R-(1-methylethenyl)-cyclohexane-1R,3R-dicarbonitrile 
• 155486-42-3 (1R,2R,3R,5R)-1-((S)-1-Cyano-2-methyl-propylamino)-5-isopropenyl-2-methyl-cyclohexane-1,3-dicarbonitrile 
• 155385-81-2 (1R,2R,3R,5R)-1-isobutylideneamino-2-methyl-5-(1-methylethenyl)cyclohexane-1,3-dicarbonitrile 

Relevant articles and documents

Dauben-Michno oxidative transposition of allylic cyanohydrins - Enantiomeric switch of (-)-carvone to (+)-carvone

Allylic cyanohydrins were subjected to Dauben-Michno oxidation at low temperatures to provide β-cyanoenones in good to excellent yields. The potential of this oxidative transposition as a means of an enantiomeric switch of enones containing a latent plane of symmetry was tested by conversion of (-)-carvone to its enantiomer.

Synthesis and analgesic-like effect of (6R, 4S)-p-Mentha-1,8-dien-6- ylmethylene-p-toluenesulfonamide

The synthesis of a monoterpene-based para-toluenesulfonamide is reported starting from naturally occurring (R)- (-)-carvone (1), by 1,2-addition of HCN followed by reduction with lithium aluminum hydride to afford the amino alcohols 3a and 3b. Tosylation

Regioselective hydration and deprotection of chiral, dissymmetric iminodinitriles in the scope of an asymmetric strecker strategy

The controlled, selective decomposition of dissymmetric iminodinitriles (DIDN) of formula RCH(CN)-NH-C(CN)R′R″ (considered as N-protected alpha-aminonitriles), is a critical issue for an original asymmetric Strecker strategy previously outlined by us for the enantioselective synthesis of amino acids. This strategy, derived from Harada's work, involves a double sequence of (i) stereoselective Strecker condensation of a chiral ketone R′R″CO with NH3 and HCN, followed by (ii) stereoselective Strecker condensation with an aldehyde RCHO and HCN, then (iii) regioselective retro-Strecker decomposition of the DIDN intermediate to release the target alpha-aminonitrile. In addition to the use of quite simple, cheap cyclic ketones (e.g. carvone derivatives) as chiral auxiliaries, another great advantage of this strategy is that step (iii) enables the recovery of the chiral ketone and hence its reuse. While our previous investigations on step (iii) under various conditions, either preceded or followed by the hydration of the secondary nitrile group RH(CN)- into an amide, had shown insufficient selectivity, we succeeded in the regioselective hydration of the secondary nitrile of DIDN without significant racemisation, by using a large excess of hydrogen peroxide in methanolic/aqueous ammonia (pH 12.5) at low temperature. The resulting imino nitrile/amide compound was then classically decomposed in acidic medium through a retro-Strecker reaction, affording the chiral alpha-amino amide. Alternately, the regioselective retro-Strecker decomposition of the tertiary moiety of the DIDN was achieved by reaction with silver cation in aqueous nitric acid, also without significant racemisation, thus establishing an original, enantioselective synthesis of alpha-aminonitriles. In both reactions, the chiral ketonic auxiliary resulting from DIDN decomposition was recovered in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.