82890-08-2

Upstream product

• 1423-60-5 methyl ethynyl ketone 
• 107815-03-2 1,3,3,4-tetramethylcyclohexan-1-ol 
• 96641-42-8 4-(6-Methylene-2,2,3-trimethylcyclohexyl)-4-hydroxy-2-butanone 
• 10463-42-0 3,4-dimethyl-cyclohex-2-enone 
• 96641-40-6 4-Dimethoxymethyl-5,5,6-trimethyl-1-oxaspiro<2.5>octane 
• 96641-38-2 3,3,4-Trimethyl-1-trimethylsiloxy-1-cyclohexene 
• 96641-41-7 6-Methylene-2,2,3-trimethylcyclohexanecarbaldehyde dimethyl acetal 
• 111923-55-8 trans-(trimethyl-3,3,4 cyclohexanone-2 yl)-3 acrylate de methyle Δ² trans 
• 917-54-4 methyllithium 
• 111923-59-2 acide cis-(trimethyl-3,3,4 methylene cyclohexane-2 yl)-3 propenoique Δ² trans 
• 74-88-4 methyl iodide 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 526-75-0 2,3-Dimethylphenol 

Downstream Products

• 72190-03-5 (-)-1t-(5c.6.6-trimethyl-2-methylene-cyclohexyl-(r))-buten-⁽¹⁾-one-⁽³⁾-(4-phenyl semicarbazone) 
• 429677-16-7 (2R,3E)-4-[(1S,3S)-2,2,3-trimethyl-6-methylidenecyclohexyl]but-3-en-2-ol 
• 429677-19-0 (2R,3E)-4-[(1S,3S)-2,2,3-trimethyl-6-methylidenecyclohexyl]but-3-en-2-ol acetate 
• 16769-63-4 (+)-1-((1Ξ)-2,2,3c,6c-tetramethyl-cyclohexyl-(r))-butanone-(3)-semicarbazone 
• 6138-84-7 (+)-1-((1Ξ)-2,2,3c,6c-tetramethyl-cyclohexyl-(r))-butanone-(3) 

Relevant academic research and scientific papers

Enzyme-mediated syntheses of the enantiomers of γ-irones

An enzymatic approach to the synthesis of all the possible stereoisomers of (E) and (Z), cis and trans-γ-irones in enantiomerically pure form from commercial Irone Alpha is described. A very efficient resolution of racemic trans-γ-irone, affording both the enantiomers in high ee and chemical purity, is also presented. Olfactory evaluation of (+)- and (-)-3b and full configuration assignment of the irone isomers contained in samples of Italian iris oil are reported.

Synthesis of (+)-(2S,6S)-trans-α-Irone and of (-)-(2S,6S)-trans-γ-Irone

A 3:1 mixture of (+)-(2S,6S)-trans-α-irone ((+)-1) and (-)-(2S,6S)-trans-γ-irone ((-)-2) has been synthesized with ca. 70 percent e. e. by the ene reaction of (-)-(S)-3 and but-3-yn-2-one.

CHIMIE DES FRAGRANCES, PARTIE II: SYNTHESE DE LA γ-IONONE ET DES CIS- ET TRANS-γ-IRONES

A new convergent synthesis of γ-ionone and cis- and trans-γ-irones is described.A tandem 1,4-addition functionnalisation reaction and a chemo- and regioselective olefination reaction are the key steps.A two dimensional NMR study allows the determination of the favoured configuration of one intermediate.

Syntheses of (+/-)-cis γ-Irone and Its Related Compounds

(+/-)-cis-γ-Irone (1a), (+/-)-cis-dihydro-γ-irone (2a) and their trans-isomers (1b, 2b) were synthesized via 3,3-(Claisen) or 2,3-sigmatropic rearrangement of 1-hydroxymethyl-3,3,4-trimethyl-1-cyclohexene (8) derivatives as each key step.

New Synthesis of trans-γ-Irone

trans-γ-Irone was successfully synthesized starting from 3,4-dimethyl-2-cyclohexenone by sevenstep reactions including TiCl4-promoted reaction of enol silyl ether and cross-aldol reaction of vinyloxyborane.

The Synthesis of (+/-)-γ-Irones

(+/-)-γ-Irones (1/9 of cis- and trans-isomers and pure trans-γ-irone) were synthesized via the intramolecular Diels-Alder reaction starting from 2,4-hexadienyl aniline derivative and β,β-dimethylacryloyl chloride.

Synthesis of The Natural Enantiomers of Irones from (+)-Citronellal

Some irone isomers with the natural chirality have been synthesised from (+)-citronellal (7). (+)-Methyl citronellate (21) obtained from compound (7) was methylated stepwise to give methyl 2,2,3,7-tetramethyloct-6-enoate (23).After hydrolysis of the ester