59633-89-5

Basic information

• Product Name: 3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid methyl ester
• Synonyms: 3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid methyl ester
• CAS NO: 59633-89-5
• Molecular Weight: 252.354
• Mol File: 59633-89-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid methyl ester(59633-89-5)
• EPA Substance Registry System: 3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid methyl ester(59633-89-5)

Safety Data

• Hazardous Substances Data: 59633-89-5(Hazardous Substances Data)

Upstream product

• 59633-88-4 2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene 
• 105-45-3 acetoacetic acid methyl ester 
• 118672-99-4 3-oxo-5-(2,6,6-trimethyl-cyclohex-2-enyl)-pentanoic acid methyl ester 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 472-20-8 β-cyclogeraniol 
• 79-77-6 (E)-β-ionone 
• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 108888-69-3 (1R,4aR,8aR)-(+)-1-(p-tosyloxy)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 59633-93-1 (1S,4aS,8aS)-(-)-1-(p-tosyloxy)methyl-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 331822-05-0 Prop-2-en-1-yl 3-oxo-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pentanoate 
• 163041-10-9 Methyl 2-[2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethyl]-4-oxo-4H-1-benzopyran-3-carboxylate 
• 79368-00-6 (Z)-3-(Diethoxy-phosphoryloxy)-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-enoic acid methyl ester 
• 152294-03-6 (E)-3-(Diethoxy-phosphoryloxy)-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-enoic acid methyl ester 
• 152294-12-7 3-[2-(2,6,6-Trimethyl-cyclohex-1-enyl)-ethyl]-4H-isoxazol-5-one 
• 59633-93-1 Toluene-4-sulfonic acid (1S,4aS,8aS)-5,5,8a-trimethyl-2-oxo-decahydro-naphthalen-1-ylmethyl ester 
• 59633-92-0 1-<<(p-tolylsulfonyl)oxy>methyl>-2-hydroxy-5,5,8a-trimethyldecahydronaphthalene 
• 59633-91-9 8ξ-hydroxy-9β-hydroxymethyl-(4α,4β),10β-trimethyl-(trans)-decahydronaphthalene 
• 95998-96-2 ((6aS,11aR)-4,4,9,11a-Tetramethyl-1,2,3,4,5,6,7,10,11,11a-decahydro-cyclohepta[a]naphthalen-6a-yl)-methanol 
• 59633-91-9 8β-hydroxy-9β-hydroxymethyl-(4α,4β),10β-trimethyl-(trans)-decahydronaphthalene 
• 59633-91-9 rac-12-nor-drimane-8α,11-diol 
• 3738-00-9 (±)-ambrox 

Relevant articles and documents

110. The Synthesis of Racemic Ambrox

(+/-)-Ambrox (10), the racemic form of (-)-Ambrox, the commercially most important ambergris odorant has been synthesized from a readily available bicyclic keto ester in five steps.The racemic ether retains the characteristic scent of fine-quality ambergris, and the odor threshold of the racemate and the (-)-enantiomer prepared from natural sclareol found to be essentially identical.

Preparation of 9α-fluorinated sesquiterpenic drimanes and evaluation of their antifeedant activities

The preparation of 9α-fluoro analogues of both natural and unnatural drimane-type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8-keto-12-nordriman-11-oate from β-ionone and entailed the electrophilic fluorination of C-9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from, the intermediate 9α-fluoro-8-keto-12-nordrimane system by means of different reactions at the C-8 ketone carbonyl group, essentially Wittig methylenation, cyanohydrin formation or palladium-catalysed carbonylation of the corresponding enol triflate. Further manipulation of the functionalization derived from these key reactions allowed the preparation, among others, of 9α-fluorodrimanes, which are structurally and functionally related to albicanic acid, drimenin and olepupuane. Also described are the reactivities of some of the fluorine-containing systems prepared and a comparative study of the antifeedant activities of a selection of 9α-fluorodrimanes and the corresponding hydrogen analogues against several, insect species with different feeding ecologies (Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), which revealed a significant increase in the antifeedant activities of some of the fluorinated drimane analogues.

Total synthesis of yahazunol, zonarone and isozonarone

The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol.

Beta-ketoester compounds

The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.