815581-75-0

Basic information

• Product Name: (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol
• Synonyms: (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol
• CAS NO: 815581-75-0
• Molecular Weight: 170.252
• Mol File: 815581-75-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol(815581-75-0)
• EPA Substance Registry System: (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol(815581-75-0)

Safety Data

• Hazardous Substances Data: 815581-75-0(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 40036-54-2 (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 1449674-46-7 ((1R,5S)-5-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)methyl pivalate 
• 1449674-34-3 (E)-4-acetoxy-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl pivalate 
• 1449674-47-8 C₁₇H₂₈O₄ 
• 1053183-31-5 (E)-4-hydroxy-3,7-dimethylocta-2,6-dien-1-yl pivalate 
• 86561-84-4 essigsaeure-<(E,R)-6,7-dihydroxy-3,7-dimethyl-2-octenyl>ester 

Downstream Products

• 815581-77-2 [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate 
• 1449674-45-6 C₁₇H₂₂O₃ 
• 1449674-39-8 (3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 1449674-32-1 (2E,4E)-5-((3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3-methylpenta-2,4-dienenitrile 
• 1449674-40-1 (2E,4E)-5-((3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal 
• 1449674-41-2 (2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal 
• 1449674-42-3 (S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone 
• 1449674-43-4 (2E,4E)-5-((3R,5S)-3,5-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal 
• 1449674-44-5 (1S,3R)-5-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-4,6,6-trimethylcyclohex-4-ene-1,3-diol 
• 1371636-45-1 (2S,6E,8E)-cyclofarnesa-4,6,8-triene-2,10,11-triol 
• 106009-58-9 (2S,7E,9E)-2,11-dihydroxy-1,6-cyclofarnesa-5,7,9-trien-4-one 
• 1449674-37-6 ((1R,5S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethylcyclohex-2-en-1-yl)methanol 
• 153060-93-6 (-)-(1R,3S)-2,2,3-trimethyl-6-methylidenecyclohexane-1-methanol 
• 153060-96-9 (+)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-methanol 

Relevant articles and documents

First total synthesis of (+)-apotrisporin e and (+)-apotrientriols A-B: A cyclization approach to apocarotenoids

The first total synthesis of the natural apocarotenoids (+)-apotrisporin E (1) and (+)-apotrientriols A and B (2-3) has been accomplished. The structure, relative stereochemistry and the assignation of the absolute configuration have been confirmed. This is a fast and easy access to this family of natural products whose key steps are a diastereoselective cyclization and a HWE olefination to attach the dienic side chain. This work also opens the door to the synthesis of other apocarotenoids such as trisporols and trisporic acids. The Royal Society of Chemistry.

Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and γ-cyclogeraniol

A comprehensive study on the lipase PS-mediated resolution of different hydroxy-geraniol isomers is reported. A number of α-, β- and γ-isomers bearing a 2-, 3- or 4-hydroxy functional group were synthesised regioselectively and then submitted to the lipase-mediated kinetic acetylation. The latter experiments showed that the 2-hydroxy isomers 4, 5 and 14 (α, γ and β, respectively) as well as cis-3-hydroxy α-cyclogeraniol 7 and cis-4-hydroxy γ-cyclogeraniol 10 could be easily resolved by this procedure. The enantiomeric purity of the main part of these compounds was increased by recrystallisation and the enantiopure diols obtained were used as building blocks for the synthesis of the natural terpenoids karahana lactone, karahana ether and crocusatin C and for the preparation of the synthetic intermediate γ-cyclogeraniol. The absolute configurations of the enantiomers of the diols 7, 10, 14 and 19 were determined by chemical correlation with the known compounds 40, 41, 39 and 41, respectively.