66395-23-1

Basic information

• Product Name: (+-)-trans-2,5-dimethyl-cyclohexanone
• Synonyms: (+-)-trans-2,5-dimethyl-cyclohexanone
• CAS NO: 66395-23-1
• Molecular Weight: 126.199
• Mol File: 66395-23-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (+-)-trans-2,5-dimethyl-cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: (+-)-trans-2,5-dimethyl-cyclohexanone(66395-23-1)
• EPA Substance Registry System: (+-)-trans-2,5-dimethyl-cyclohexanone(66395-23-1)

Safety Data

• Hazardous Substances Data: 66395-23-1(Hazardous Substances Data)

Upstream product

• 13368-65-5 (3R)-3-methylcyclohexanone 
• 95-92-1 oxalic acid diethyl ester 
• 74-88-4 methyl iodide 
• 53288-39-4 1-Acetoxy-2,5-dimethyl-cyclohexen 
• 3809-32-3 2,5-dimethylcyclohexanol 
• 925-90-6 ethylmagnesium bromide 
• 20968-77-8 pyrrolidine enamine de la dimethyl-2,5 cyclohexanone 
• 583-60-8 2-Methylcyclohexanone 
• 36504-12-8 2-bromo-6-methylcyclohexanone 
• 6610-21-5 6-methylcyclohex-2-en-1-one 
• 917-54-4 methyllithium 
• 2207-04-7 trans-1,4-dimethylcyclohexane 
• 932-51-4 (+/-)-cis-2,5-dimethyl-cyclohexanone 
• 19781-46-5 1-Methylen-2α.5β-dimethyl-cyclohexan 

Downstream Products

• 2542-87-2 (+/-)-2r.5t-dimethyl-1-hydroxymethylene-cyclohexanone-⁽⁶⁾ 
• 4500-14-5 (+/-)-trans-2,5-dimethyl-cyclohexanone oxime 
• 3127-81-9 trans-2,5-dimethylcyclohexanol (1,2 trans) 
• 3127-81-9 trans-2,5-dimethylcyclohexanol (1,2 cis) 
• 932-51-4 (+/-)-cis-2,5-dimethyl-cyclohexanone 
• 169275-20-1 (3R,6R)-trans-3,6-dimethylcyclohexene 
• 169215-44-5 (1R,2R,3R,6R)-3,6-dimethylcyclohexane-1,2-diamine 
• 169215-48-9 C₂₂H₃₀N₂O₄S₂ 
• 169275-21-2 N-((1R,2R,3R,6R)-2-Azido-3,6-dimethyl-cyclohexyl)-4-methyl-benzenesulfonamide 
• 169215-47-8 (1R,2R,3R,4R)-2-Azido-3-iodo-1,4-dimethyl-cyclohexane 
• 42185-47-7 (2S)-2r,3t,6c-trimethyl-cyclohexanone 

Relevant articles and documents

The selective functionalization of saturated hydrocarbons. Part 36. Stereoselectivity studies of Gif-type reactions

The stereoselectivity of various Gif-type reactions was evaluated using trans-1,4-dimethylcyclohexane as a chemical probe. The results revealed that these reactions were moderately stereoselective. The outcome of the reactions was preferentially formed in the more stable equatorial configuration.

Stereoselective oxidation of alkanes with: M -CPBA as an oxidant and cobalt complex with isoindole-based ligands as catalysts

Two complexes with isoindole-core ligands of general formula [M{C6H4C(NH2)NC(ONCMe2)2}2](NO3)2 (M = Co for 1 and M = Ni for 2) were studied as catalysts for the mild stereoselective alkane oxidation with m-chloroperbenzoic acid (m-CPBA) as an oxidant and cis-1,2-dimethylcyclohexane (cis-1,2-DMCH) as a main model substrate. Complex 1 disclosed a pronounced activity, with high retention of stereoconfiguration of substrates (>98% for cis-1,2-DMCH) and highest cis/trans ratio of tertiary alcohols (products) of 56, under mild conditions. The best achieved yields of tertiary cis-alcohols were of 13.7 and 50.5%, based on the substrate (cis-1,2-DMCH) and the oxidant (m-CPBA) respectively. Kinetic experiments, high bond and stereoselectivity parameters, kinetic isotope effect of 7.2(2) in the oxidation of cyclohexane, and incorporation of 18O from H218O support the involvement of CoIVO high-valent metal-oxo intermediates as main C-H attacking species.

Diastereo- and enantioselective synthesis of dimethylcyclohexanamines by asymmetric reductive amination

A series of optically active dimethylcyclohexanamines 6a-c, e, with ee values ranging from 86- > 99%, have been synthesised by asymmetric reductive amination of the corresponding racemic diastereomeric cyclohexanones 3a-c, e. Their conformation and configuration are also discussed.