79-68-5

Basic information

• Product Name: 4-(2,2,3-trimethyl-6-methylenecyclohexyl)-3-buten-2-one
• Synonyms: 4-(2,2,3-trimethyl-6-methylenecyclohexyl)-3-buten-2-one;gamma-irone;3-Buten-2-one, 4-(2,2,3-trimethyl-6-methylenecyclohexyl)-;Einecs 201-218-0;g-Irone
• CAS NO: 79-68-5
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.32388
• EINECS: 201-218-0
• Mol File: 79-68-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 25°C
• Boiling Point: bp0.06 85-88°; bp2 114-116°
• Flash Point: 118.7°C
• Appearance: /
• Density: d415 0.939
• Vapor Pressure: 0.00405mmHg at 25°C
• Refractive Index: nD15 1.505
• CAS DataBase Reference: 4-(2,2,3-trimethyl-6-methylenecyclohexyl)-3-buten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,2,3-trimethyl-6-methylenecyclohexyl)-3-buten-2-one(79-68-5)
• EPA Substance Registry System: 4-(2,2,3-trimethyl-6-methylenecyclohexyl)-3-buten-2-one(79-68-5)

Safety Data

• Hazardous Substances Data: 79-68-5(Hazardous Substances Data)

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 
• 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 
• 74-88-4 methyl iodide 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 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 
• 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) 
• 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 
• 429677-16-7 (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 

Relevant articles and documents

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.