49816-69-5

Basic information

• Product Name: 3-Buten-2-one, 4-(2,2-dimethyl-6-methylenecyclohexyl)-, (3E)-
• CAS NO: 49816-69-5
• Molecular Formula: C13H20O
• Molecular Weight: 192.301
• Mol File: 49816-69-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-Buten-2-one, 4-(2,2-dimethyl-6-methylenecyclohexyl)-, (3E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-2-one, 4-(2,2-dimethyl-6-methylenecyclohexyl)-, (3E)-(49816-69-5)
• EPA Substance Registry System: 3-Buten-2-one, 4-(2,2-dimethyl-6-methylenecyclohexyl)-, (3E)-(49816-69-5)

Safety Data

• Hazardous Substances Data: 49816-69-5(Hazardous Substances Data)

Upstream product

• 13927-47-4 (3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one 
• 141-10-6 pseudoionone 
• 58689-15-9 pseudoionone 
• 141-10-6 pseudoionone 
• 61175-95-9 2-Dimethoxymethyl-1,1-dimethyl-3-methylene-cyclohexane 
• 432-23-5 2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde 
• 61175-94-8 4-Dimethoxymethyl-5,5-dimethyl-1-oxa-spiro[2.5]octane 
• 107197-11-5 (dimethyl-3,3-cyclohexanone-2yl)-3-acrylate de methyle Δ² trans 
• 111923-56-9 (dimethyl-3,3 methylene cyclohexane-2 yl)-3 acrylate de methyle Δ² trans 
• 72203-98-6 (3E)-3,7-dimethyl-3,6-octadienal 
• 72203-97-5 cis-isocitral 
• 55050-40-3 7-methyl-3-methylene-6-octenal 
• 73956-64-6 ethyl 2,2-dimethyl-6-methylenecyclohexane-1-carboxylate 
• 472-19-5 (2,2-dimethyl-6-methylenecyclohexyl)methanol 

Downstream Products

• 49817-20-1 γ-Ionylidenaethanol 
• 29789-62-6 (2Z,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 99280-18-9 ethyl-5-(2,2-dimethyl-6-methylene)cyclohexyl-3-methyl-2,4-pentadienoate 
• 99280-17-8 (+/-)-(2Z,4E)-ethyl γ-ionylideneacetate 
• 39900-13-5 2-Methylene-6,6-dimethyl-1-[1,3-dioxo-1-but-1-yl]-cyclohexane 
• 24190-33-8 (+)-(S)-dihydro-γ-ionone 
• 52612-51-8 (+)-(1'R,6'S)-4-(2',2',6'-trimethylcyclohexyl)butan-2-one 
• 34815-98-0 lycopene 
• 49817-21-2 γ-apo-12'-Karotenal 
• 34143-90-3 trans-β,γ-Caroten 
• 3738-00-9 (3aRS,5aSR,9aSR,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan 
• 133859-01-5 (E)-4-Methyl-6-(2',2'-dimethyl-6'-methylidenecyclohexyl)hex-3-en-1-ol 
• 133859-02-6 (Z)-4-Methyl-6-(2',2'-dimethyl-6'-methylidenecyclohexyl)hex-3-en-1-ol 
• 138152-09-7 2-Methyl-2-<2'-(2'',6'',6''-trimethylcyclohex-1''-enyl)ethyl>tetrahydrofuran 

Relevant articles and documents

Regioselective catalysed H-ene reaction of allylsilanes with 3-butyn-2-one application to a new synthesis of (±)-γ-ionone

An unexpected ZnI2 catalysed regioselective H-ene reaction between allysilanes and butynone in the presence of molecular sieves 4A is reported. The silyl group dramatically enhanced the rate of the reaction which is used as a key for a new synt

Synthesis of ionones on solid Br?nsted acid catalysts: Effect of acid site strength on ionone isomer selectivity

The effect of Br?nsted acid site strength on the liquid-phase conversion of pseudoionone to ionone isomers (α-, β- and γ-ionone) was studied on resin Amberlyst 35W, silica-supported heteropolyacid (HPAS) and silica-supported triflic acid (TFAS). Catalyst acidity was probed by temperature-programmed desorption of NH3 coupled with infrared spectra of adsorbed pyridine. The initial pseudoionone conversion rate followed the order: TFAS > Amberlyst 35W ≈ HPAS. Synthesis of the three ionone isomers occurred via a common cyclic carbocation intermediate formed from the activation of the pseudoionone molecule on Br?nsted acid sites. Initial ionone mixtures containing a α:β:γ isomer distribution of about 40:20:40 were formed, irrespective of the acid site strength. But the ionone mixture composition changed with the progress of the reaction because γ-ionone was consecutively converted to α-ionone on HPAS and Amberlyst 35W, whereas the stronger acid sites of TFAS converted γ-ionone to β-ionone.

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.