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Usage

Uses

Used in Organic Synthesis:
[1alpha(E),3beta]-4-(2,2,3-trimethyl-6-methylenecyclohexyl)but-3-en-2-one is used as a key intermediate in organic synthesis for the creation of a wide range of bioactive molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of pharmaceuticals and other biologically active compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, [1alpha(E),3beta]-4-(2,2,3-trimethyl-6-methylenecyclohexyl)but-3-en-2-one is used as a building block for the development of new drugs. Its potential pharmacological and biological activities are of interest to researchers and drug developers, who aim to leverage its properties to create novel therapeutic agents.
Used in Research and Development:
Due to its complex structure and potential for various reactions, [1alpha(E),3beta]-4-(2,2,3-trimethyl-6-methylenecyclohexyl)but-3-en-2-one is also utilized in research and development settings. Scientists explore its reactivity and potential applications in creating new materials and compounds with specific properties for various industries, including but not limited to the pharmaceutical sector.
Overall, [1alpha(E),3beta]-4-(2,2,3-trimethyl-6-methylenecyclohexyl)but-3-en-2-one is a versatile chemical with applications in organic synthesis, pharmaceuticals, and research, driven by its unique structural features and reactivity.

Upstream product

• 67-64-1 acetone 
• 1423-60-5 methyl ethynyl ketone 
• 107815-03-2 1,3,3,4-tetramethylcyclohexan-1-ol 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 917-54-4 methyllithium 
• 111923-59-2 acide cis-(trimethyl-3,3,4 methylene cyclohexane-2 yl)-3 propenoique Δ² trans 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 74-88-4 methyl iodide 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 86590-04-7 N-(2E,4E-hexadienyl)-N-(2-hydroxyphenyl)-3-methyl-2-butenoamide 
• 13395-76-1 2,3-dimethylcyclohexanone 
• 526-75-0 2,3-Dimethylphenol 
• 408309-84-2 2,2,3-trimethyl-6-oxocylohexanecarboxylic acid ethyl ester 
• 101170-42-7 2,2,3-trimethyl-6-methylene-cyclohexanecarboxylic acid ethyl ester 

Downstream Products

• 72190-03-5 (-)-1t-(5c.6.6-trimethyl-2-methylene-cyclohexyl-(r))-buten-⁽¹⁾-one-⁽³⁾-(4-phenyl 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 
• 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.

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.

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.

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.