317801-55-1

Basic information

• Product Name: Cyclohexanol, 5-methylene-2-(1-methylethyl)-, (1R,2R)- (9CI)
• Synonyms: Cyclohexanol, 5-methylene-2-(1-methylethyl)-, (1R,2R)- (9CI)
• CAS NO: 317801-55-1
• Molecular Formula: C10H18O
• Molecular Weight: 154.24932
• Product Categories: ISOPROPYL
• Mol File: 317801-55-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexanol, 5-methylene-2-(1-methylethyl)-, (1R,2R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 5-methylene-2-(1-methylethyl)-, (1R,2R)- (9CI)(317801-55-1)
• EPA Substance Registry System: Cyclohexanol, 5-methylene-2-(1-methylethyl)-, (1R,2R)- (9CI)(317801-55-1)

Safety Data

• Hazardous Substances Data: 317801-55-1(Hazardous Substances Data)

Upstream product

• 317801-57-3 (4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone 
• 317801-61-9 (R)-(+)-2-isopropyl-5-methylhex-5-ene-1-carboxylic acid 
• 264258-71-1 (R)-(+)-2-isopropyl-5-methylhex-5-en-1-ol 
• 212620-36-5 (R)-(-)-2-isopropyl-5-methylhex-5-enal 
• 1220632-49-4 2-isopropyl-5-{[dimethyl(phenyl)silyl]methyl}-1,2-epoxy-5-hexene 
• 264258-73-3 (+/-)-2-Isopropyl-5-methylhex-5-en-1-ol 
• 97690-18-1 (+/-)-2-isopropyl-5-methylhex-5-ene-1-carboxylic acid 
• 503-74-2 3-methylbutyric acid 
• 36584-59-5 2,6-dimethylhept-6-en-3-one 
• 590-86-3 isovaleraldehyde 
• 41807-59-4 N-(3-Methylbutylidene)cyclohexylamine 
• 189076-44-6 2-Isopropyl-2-(3-methyl-but-3-enyl)-oxirane 
• 97690-19-2 (+/-)-2-Isopropyl-5-methylhex-5-enal 

Relevant articles and documents

Synthesis of 3-methylenecyclohexan-1-ols by lewis acid catalyzed cyclization of (epoxy-allyl)silanes

A new route for the synthesis of (epoxy-allyl)silanes bearing the PhMe 2Si group has been developed and their acid-catalyzed cyclization studied. The so-called normal products derived from 5-exo or 6-endo attack were never obtained. On the contrary, an interesting tandem rearrangement/cyclization process was observed, which selectively led to 3-methylenecyclohexan-1-ols. A mechanism is proposed to explain this tandem reaction. The stereoselectivity of the cyclization process depends on the nature of the catalyst.

Catalytic and stoichiometric Lewis acid participation in aldehyde ene cyclisations

Racemic 2-isopropyl-2-methylhex-5-enal has been synthesised in order to probe ene cyclisations leading to menthol analogues. The objective was first to discover catalytic conditions for preferential cyclisation to the menthol rather than the neomenthol series and then to develop (dynamic) kinetic resolution procedures which afforded a single enantiomer of product. It was found that catalytic quantities of both Me2AlCl and a bulky methyl-aluminium bis(phenoxide) reagent gave products attributed to a Meerwein-Pondorff-Verley reaction. In this the aldehyde is reduced to a primary alcohol and the ene product oxidised to the corresponding α,β-unsaturated ketone. By contrast, a related bulky chloroaluminium reagent catalysed the ene cyclisation cleanly, but preferentially to the undesired neomenthyl stereoisomer.

Unprecedented stereochemical control in the intramolecular ene-reactions of δ,ε-unsaturated aldehydes using exceptionally bulky organoaluminum reagents: Elucidation of the transition state

Unprecendented stereochemical control has been achieved in the type II intramolecular ene reactions of δ,ε-unsaturated aldehydes leading to trans-cyclohexanols with excellent selectivity under very mild conditions, using exceptionally bulky methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR). Success of the stereocontrolled cyclization can be ascribable to the ability of this modified organoaluminum reagents, MABR, to change the conformation of the transition state. Examining the ene reactions of substrates 7, 11, 14 with MABR, the stereochemical outcome of the present organoaluminum-promoted intramolecular ene reactions is further elucidated.