79-68-5

Usage

InChI:InChI=1/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h8-9,11,13H,1,6-7H2,2-5H3/b9-8+/t11-,13+/m1/s1

Upstream product

• 645-68-1 (3E,5Ξ)-6,9,10-trimethyl-undeca-3,5,9-trien-2-one 
• 67-64-1 acetone 
• 917-54-4 methyllithium 
• 111923-59-2 acide trans-(trimethyl-3,3,4 methylene cyclohexane-2 yl)-3 propenoique Δ² trans 
• 96641-42-8 4-(6-Methylene-2,2,3-trimethylcyclohexyl)-4-hydroxy-2-butanone 
• 74-88-4 methyl iodide 
• 101170-42-7 2,2,3-trimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester 
• 408309-84-2 2,2,3-trimethyl-6-oxocylohexanecarboxylic acid ethyl ester 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 90974-65-5 1-hydroxymethyl-3,3,4-trimethyl-1-cyclohexene 
• 1502-24-5 2,3-dimethylcyclohexan-1-ol 
• 86590-04-7 N-(2E,4E-hexadienyl)-N-(2-hydroxyphenyl)-3-methyl-2-butenoamide 
• 10463-42-0 3,4-dimethyl-cyclohex-2-enone 
• 96641-38-2 3,3,4-Trimethyl-1-trimethylsiloxy-1-cyclohexene 

Downstream Products

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

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.

STEREOCHEMISTRY OF THE CYCLIZATION OF PSEUDOIRONE AT ELEVATED TEMPERATURE

The cyclization of pseudoirone (6,9,10-trimethyl-3,5,9-undecatrien-2-one) in the presence of a catalytic amount of phosphoric acid at 110 deg C gives a high yield and leads to the preferential formation of α-irone.It was established that if the reaction was conducted in the presence of protic acids 1-(1,3,4-trimethyl-3-cyclohexenyl)-1-penten-4-one was formed in addition to the α, β, and γ isomers.

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.