72074-86-3

Basic information

• Product Name: (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on
• Synonyms: (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on
• CAS NO: 72074-86-3
• Molecular Weight: 206.328
• Mol File: 72074-86-3.mol

Chemical Properties

• CAS DataBase Reference: (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on(CAS DataBase Reference)
• NIST Chemistry Reference: (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on(72074-86-3)
• EPA Substance Registry System: (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on(72074-86-3)

Safety Data

• Hazardous Substances Data: 72074-86-3(Hazardous Substances Data)

Upstream product

• 645-68-1 pseudoirone 
• 142787-74-4 (3E)-6,9,10-trimethylundeca-3,5,8-trien-2-one 
• 1423-60-5 methyl ethynyl ketone 
• 107815-03-2 1,3,3,4-tetramethylcyclohexan-1-ol 
• 645-68-1 (3E,5Ξ)-6,9,10-trimethyl-undeca-3,5,9-trien-2-one 
• 52567-96-1 3,6,7-trimethyl-oct-6-en-1-yn-3-ol 
• 72074-86-3 (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on 
• 58307-67-8 3,6,7-trimethyl-6-octen-1-en-3-ol 
• 3899-32-9 (E)-3,6,7-trimethylocta-2,6-dien-1-ol 
• 687-68-3 5,6-dimethyl-5-hepten-2-one 
• 72049-80-0 4-Benzenesulfonyl-4-((1R,5R)-2,5,6,6-tetramethyl-cyclohex-2-enyl)-butan-2-ol 
• 72049-75-3 2,6-Dimethyl-8-(phenylsulfonyl)-6(Z)-octen-3-one 
• 72049-74-2 3-Bromo-2,6-dimethyl-8-(phenylsulfonyl)-6(Z)-octen-2-ol 
• 72049-71-9 6-epi-1,4-α,5,5-tetramethyl-1-α-[(phenylsulfonyl)-methyl]-cyclohexene 

Downstream Products

• 6138-84-7 (+/-)-4-(2,2,3t,6c-tetramethyl-cyclohex-r-yl)-butan-2-one 
• 72074-84-1 beta-irone 
• 564-76-1 (+/-)(2Ξ)-4t-((1Ξ)-2,5t,6,6-tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-ol 
• 79-69-6 Neoiso-α-iron 
• 27687-81-6 (+/-)-4t-(2,5,6,6-tetramethyl-cyclohex-1-enyl)-but-3-en-2-one-(2,4-dinitro-phenylhydrazone); (+/-)-trans-β-iron-(2,4-dinitro-phenylhydrazone) 
• 16769-63-4 (+/-)-4-(2,2,3t,6c-tetramethyl-cyclohex-r-yl)-butan-2-one semicarbazone 
• 95851-08-4 1-(2,2,t-3,c-6-Tetramethyl-r-1-cyclohexyl)-3-hexanol 
• 81456-93-1 (1'RS,5'SR)-4-(2',5',6',6'-tetramethylcyclohex-2'-enyl)butan-2-one 

Relevant articles and documents

Cyclization of cis- and trans-6,7-trans-8,9-Pseudoirones in Super Acids

Stable cations from 2,3,6-trimethyl-6Z,E,8E-undecadien-10-ones (cis- and trans-pseudoirones) were generated in the HSO3F-SO2FCl system fot the first time.Configuration of the conjugated C6=C7 double bond in these ketones substantiall

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.

An Alternative Access to (+/-)-α-Irones and (+/-)-β-Irone via Acid-Mediated Cyclisation

Acid-mediated cyclisation of trienone 8, readily available from 2,3-dimethylbutanal (1; five steps: 47percent yield), using fluorosulfonic acid (6.8 mol-equiv.) in 2-nitropropane at -70 deg, afforded a 14:9:1 mixture (70percent yield) of (+/-)-cis-α-irone

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.

Stereoselective Synthesis of (+/-)-Irones

β-, α-cis-, and α-trans-irones (1, 2a, and 2b) have been prepared via 2,5,6,6-tetramethyl-1-cyclohexene (7) and 1,4β,5,5-tetramethyl-6β-cyclohexene (8a) and its C-6 epimer (8b).Electrochemical epoxidation of