199177-32-7

Basic information

• Product Name: (+/-)-2-hydroxy-β-cyclogeraniol
• Synonyms: (+/-)-2-hydroxy-β-cyclogeraniol
• CAS NO: 199177-32-7
• Molecular Weight: 170.252
• Mol File: 199177-32-7.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-2-hydroxy-β-cyclogeraniol(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2-hydroxy-β-cyclogeraniol(199177-32-7)
• EPA Substance Registry System: (+/-)-2-hydroxy-β-cyclogeraniol(199177-32-7)

Safety Data

• Hazardous Substances Data: 199177-32-7(Hazardous Substances Data)

Upstream product

• 152328-14-8 3-Hydroxymethyl-2,2,4-trimethyl-cyclohex-3-enone 
• 162376-82-1 2,6,6-Trimethyl-1,4-cyclohexadiene-1-carboxaldehyde 
• 209069-55-6 5-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enecarbaldehyde 
• 37715-31-4 (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate 
• 66465-72-3 5-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 199177-31-6 (2,2,4-Trimethyl-7-oxa-bicyclo[4.1.0]hept-3-en-3-yl)-methanol 
• 199177-35-0 3-Methoxymethoxymethyl-2,2,4-trimethyl-7-oxa-bicyclo[4.1.0]hept-3-ene 
• 199177-30-5 2-Methoxymethoxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene 

Downstream Products

• 1178893-14-5 C₁₂H₂₀O₃ 
• 1178893-16-7 C₁₄H₂₂O₄ 
• 144066-84-2 Acetic acid 2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester 
• 150966-63-5 3-(tert-butyldimethylsiloxymethyl)-2,2,4-trimethyl-cyclohex-3-ene-1-one 
• 199177-36-1 Acetic acid 5-hydroxy-2,6,6-trimethyl-cyclohex-1-enylmethyl ester 

Relevant articles and documents

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 novel approach to the Taxol A-ring synthetic equivalents

A novel short approach to the A-ring synthetic equivalents of Taxol was described. Oxabicyclic ketone 3 served as a versatile template for selective functionalization leading to oxabicyclic vinylic ether 6 in two steps, which was hydrolyzed under mild aci

Stereo- and regio-selective Ti-mediated radical cyclization of epoxy-alkenes: Synthesis of the A and C ring synthons of paclitaxel

We have developed a practical synthetic route for the A and C rings of paclitaxel. The key reaction is a Ti-mediated radical cyclization of an epoxyalkene.

Taxol synthesis: Synthesis of A-ring and a methodology for substituted cyclohexadienes

A fully functionalised synthesis of taxol A-ring, through Michael/Wittig reaction and regioselective opening epoxide as key steps and also a methodology for substituted cyclohexadienes through tandem Michael/Wittig reaction is described.