13148-94-2

Basic information

• Product Name: 1-Cyclohexene-1-carboxylic acid, 2-methyl-
• CAS NO: 13148-94-2
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Mol File: 13148-94-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1-Cyclohexene-1-carboxylic acid, 2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylic acid, 2-methyl-(13148-94-2)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylic acid, 2-methyl-(13148-94-2)

Safety Data

• Hazardous Substances Data: 13148-94-2(Hazardous Substances Data)

Upstream product

• 13148-93-1 2-methyl-cyclohexa-1,4-dienecarboxylic acid 
• 98559-42-3 1-bromo-2-methyl-cyclohexanecarboxylic acid 
• 84307-85-7 2--1-methylcyclohexanol 
• 122093-62-3 1-bromo-1-methyl-2-(bromodifluoromethyl)cyclohexane 
• 591-49-1 1-methylcyclohex-1-ene 
• 122135-83-5 ethyl 2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 17649-90-0 2-(bis-methylsulfanyl-methylene)-cyclohexanone 
• 148227-28-5 4-(2-methyl-cyclohexylidene)-2-phenyl-4H-oxazol-5-one 
• 104654-69-5 Ethyl 2-methyl-1-cyclohex-1-ene carboxylate 
• 98559-42-3 (+/-)-1-bromo-2c-methyl-cyclohexane-r-carboxylic acid 
• 90199-13-6 2-methylcyclohex-2-ene-1-carboxylic acid 
• 15719-64-9 methylammonium carbonate 
• 66309-76-0 1-hydroxymethyl-1-cyclohexene-2-carboxylic acid lactone 

Downstream Products

• 3128-06-1 5-ketohexanoic acid 
• 1643935-83-4 (1S,7aS)-phenyl 3-hydroxy-1,7a-dimethyl-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indene-1-carboxylate 
• 1643935-72-1 (E)-naphthalen-2-yl 3-(benzhydryloxy)-2-methyl-4-(2-methylcyclohex-1-en-1-yl)-4-oxobut-2-enoate 
• 1643935-68-5 (E)-phenyl 3-(benzhydryloxy)-2-methyl-4-(2-methylcyclohex-1-en-1-yl)-4-oxobut-2-enoate 
• 74517-10-5 2-Methyl-1-cyclohex-1-ene carboxylic acid chloride 
• 25662-38-8 2-methyl-1-cyclohexenecarboxylic acid methyl ester 

Relevant articles and documents

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Catalytic enantioselective nazarov cyclization: Construction of vicinal all-carbon-atom quaternary stereocenters

The diastereoselective asymmetric synthesis of vicinal all-carbon-atom quaternary stereocenters is a challenging problem in organic synthesis for which only few solutions have been described. A catalytic asymmetric Nazarov cyclization of fully substituted dienones that provides cyclopentenone derivatives with vicinal quaternary stereocenters in high optical purity and as single diastereoisomers is now reported.

Asymmetric synthesis of 2-methyl cyclohexane carboxylic acids by heterogeneous catalysis: Mechanistic aspects

The catalytic hydrogenation of (S)-alkyl-N-(2-methylbenzoyl)pyroglutamates was studied over supported rhodium and ruthenium catalysts at room temperature and a pressure of 5 MPa. The reaction was diastereoselective with the predominant formation of (1S,2R)-2-methylcyclohexane carboxylic acid with a diastereomeric excess (de) of up to 96%. The most stable conformation was determined by means of a combination of modelling calculations, NMR spectroscopy and X-ray structural determination. In this conformation, the carbonyl group of the pyroglutamate auxiliary shields one face of the aromatic ring. The observed selectivity may thus be explained by a preferential adsorption at the unshielded face which avoids steric repulsion by the C=O group to result in a cis hydrogenation. The addition of an amine, the nature of the support (alumina or active carbon) or of the metal (Rh or Ru) were shown to give additional stabilisation of the adsorption at the unshielded face to increase the diastereoisomeric excess.