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

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

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

Downstream Products

• 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 

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.

Acid-catalyzed cyclization of terpenes under homogeneous and heterogeneous conditions as probed through stereoisotopic studies: A concerted process with competing preorganized chair and boat transition states

Based on stereoisotopic studies and β-secondary isotope effects, we propose that the acid-catalyzed cyclization of geranyl acetate proceeds through a concerted mechanism. Under heterogeneous conditions (zeolite Y confinement), a preorganized chairlike transition state predominates, whereas under homogeneous conditions the boat-and chairlike transition states are almost isoenergetic. For the case of farnesyl acetate, we propose that under homogeneous conditions a concerted dicyclization occurs with a preorganized boat-chair transition state competing with the chair-chair transition state. Under zeolite confinement conditions, the chair-chairlike dicyclization transition state is highly favorable. The preference of chairlike transition states within the cavities of zeolite Y is attributed to a transition state shape selectivity effect.

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.

A simple and efficient highly enantioselective synthesis of α-ionone and α-damascone

An efficient highly enantioselective (ee ≥99%) synthesis of α-ionone and α-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-α-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl4-promoted biomimetic cyclization of (6S)- or (6E)-(Z)-6,7-epoxygeraniol, respectively, followed by deoxygenation of the so formed secondary alcohol. The chiral information was encoded by a highly regioselecive Sharpless asymmetric dihydroxylation of inexpensive geranyl acetate.