69685-64-9

Basic information

• Product Name: (1S,5S)-5-methyl-2-cyclohexenol
• Synonyms: (1S,5S)-5-methyl-2-cyclohexenol
• CAS NO: 69685-64-9
• Molecular Weight: 112.172
• Mol File: 69685-64-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (1S,5S)-5-methyl-2-cyclohexenol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5S)-5-methyl-2-cyclohexenol(69685-64-9)
• EPA Substance Registry System: (1S,5S)-5-methyl-2-cyclohexenol(69685-64-9)

Safety Data

• Hazardous Substances Data: 69685-64-9(Hazardous Substances Data)

Upstream product

• 22049-46-3 (±)-cis-5-methyl-2-cyclohexenol 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 67-64-1 acetone 
• 7214-50-8 5-methylcyclohex-2-en-1-one 
• 61692-48-6 3-Isobutoxy-5-methyl-cyclohex-2-enone 
• 4341-24-6 5-methylcyclohexan-1,3-dione 
• 61221-48-5 trans-5-methyl-2-cyclohexen-1-yl acetate 
• 7601-90-3 perchloric acid 
• 52393-62-1 trans-5-methyl-2-cyclohexen-p-nitrobenzoate 
• 7318-66-3 5-methylcyclohex-2-enyl chloride 
• 79-11-8 chloroacetic acid 
• 555-31-7 aluminum isopropoxide 
• 98-80-6 phenylboronic acid 
• 32316-92-0 naphthalene-2-boronic acid 

Downstream Products

• 116783-31-4 (1R)-trans-5-methyl-cyclohex-2-enol 
• 914652-13-4 (1S)-trans-5-methyl-cyclohex-2-enol 
• 18913-27-4 trans-5-methylcyclohex-2-enyl chloride 
• 3718-55-6 trans-5-methyl-2-cyclohexen-1-one 
• 7318-66-3 (3R)-trans-3-chloro-5-methyl-cyclohexene 
• 54307-74-3 (R)-5-methyl-cyclohex-2-enone 
• 903576-80-7 phthalic acid mono-((1R)-trans-5-methyl-cyclohex-2-enyl ester) 
• 73610-85-2 cis-5-Methyl-2-cyclohexenylacetat 
• 7318-66-3 (3R)-cis-3-chloro-5-methyl-cyclohexene 

Relevant articles and documents

Kinetic Resolution of 5-Substituted Cyclohexenols by Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction

The kinetic resolution of 2-substituted-cyclohexenols via palladium-catalyzed asymmetric redox-relay Heck reaction was realized, providing optically active 2-substituted cyclohexenols and trans-3,5-disubstituted cyclohexan-1-ones in high yield and good en

Mitsunobu Reaction of Unbiased Cyclic Allylic Alcohols

The stereochemical inversion of unbiased allylic alcohols using triphenylphosphine, diethyl azodicarboxylate, and benzoic acid, commonly known as the Mitsunobu reaction, was studied in three different solvents with specific attention toward the product composition. The results generated for the Mitsunobu reaction of (R)-3-deuterio-2-cyclohexen-1-ol and the cis and trans isomers of 1-deuterio-5-methyl-2-cyclohexen-1-ol, 1-deuterio-5-tert-butyl-2-cyclohexen-1-ol, and optically active cis and trans 5-isopropyl-2-methyl-2-cyclohexen-1-ol all gave similar product distributions with respect to inversion and retention at the carbinol center as well-as syn and anti Sn2′ type addition when THF or benzene was used as the solvent (CH2Cl2 gave less selective product distributions). Interestingly, it was found that the quasi-equatorial and quasi-axial nature of the starting allylic alcohol does not appear to affect the product distribution for this reaction, nor does methyl substitution at the central carbon of the allylic alcohol. In all cases, significant amounts (8-28%) of non-SN2 type products were detected for these sterically unbiased allylic alcohols; only 72-77% of the product was from SN2 type reaction when sterically undemanding (R)-S-deuterio-2-cyclohexen-1-ol was subjected to Mitsunobu conditions.

REGIO- AND STEREO-CHEMISTRY IN ALLYLATION OF ARYL GRINARD REAGENTS CATALYZED BY PHOSPHINE-NICKEL AND -PALLADIUM COMPLEXES

Nickel and palladium complexes with the 1,1'-bis(diphenylphosphino)ferrocene ligand effectively catalyze regioselective cross-coupling of allylic ethers such as 1- or 3-methyl-2-propenyl silyl ethers with aryl-Grinard reagents, where the nickel catalyst l