13120-66-6

Basic information

• Product Name: 3-hydroxy-5-methyl-2-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione
• Synonyms: 2-(1,5-Dimethyl-4-hexenyl)-3-hydroxy-5-methyl-2,5-cyclohexadiene-1,4-dione; 2-(1,5-Dimethyl-4-hexenyl)-3-hydroxy-5-methylbenzo-1,4-quinone; 2-(1,5-Dimethyl-4-hexenyl)-3-hydroxy-5-methyl-p-benzoquinone; 2-(1,5-dimethylhex-4-en-1-yl)-3-hydroxy-5-methylbenzo-1,4-quinone; 2,5-cyclohexadiene-1,4-dione, 2-(1,5-dimethyl-4-hexen-1-yl)-3-hydroxy-5-methyl-; 2,5-cyclohexadiene-1,4-dione, 2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-; 3-Hydroxy-5-methyl-2-(6-methylhept-5-en-2-yl)-1,4-benzoquinone
• CAS NO: 13120-66-6
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Mol File: 13120-66-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 359.3°C at 760 mmHg
• Flash Point: 185.3°C
• Density: 1.103g/cm³
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: 3-hydroxy-5-methyl-2-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-5-methyl-2-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione(13120-66-6)
• EPA Substance Registry System: 3-hydroxy-5-methyl-2-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione(13120-66-6)

Safety Data

• Hazardous Substances Data: 13120-66-6(Hazardous Substances Data)

Upstream product

• 100761-40-8 (+/-)-2-(1,5-dimethyl-4-hexenyl)-3-methoxy-5-methyl-2,5-cyclohexadiene-1,4-dione <(+/-)-O-methylperezone> 
• 100668-78-8 (+/-)-leucoperezone trimethyl ether 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 180303-11-1 Trifluoro-methanesulfonic acid 5-methyl-1-methylene-hex-4-enyl ester 
• 98678-84-3 2-(5-Methoxy-7-methyl-benzo[1,3]dioxol-4-yl)-6-methyl-hept-5-en-2-ol 
• 98678-83-2 5-methyl-3,4-(methylenedioxy)anisole 
• 55950-26-0 5-methoxy-2,3-methylenedioxybromobenzene 
• 66799-94-8 5-bromo-3,4-(methylenedioxy)phenol 
• 98678-85-4 (+/-)-2-(6'-methyl-5'-hepten-2'-yl)-5-methyl-3,4-(methylenedioxy)anisole 
• 19522-96-4 7-bromo-benzo[1,3]dioxole-5-carbaldehyde 
• 124175-69-5 (+/-)-3-tert-butoxy-2-(1,5-dimethylhex-4-enyl)-5-methylcyclohexa-2,5-diene-1,4-dione 

Downstream Products

• 100761-40-8 (+/-)-2-(1,5-dimethyl-4-hexenyl)-3-methoxy-5-methyl-2,5-cyclohexadiene-1,4-dione <(+/-)-O-methylperezone> 
• 3600-95-1 (-)-perezone 
• 97763-23-0 1-hydroxycurcuquinone 
• 648408-93-9 2-(1,5-dimethyl-4-hexenyl)-3-hydroxy-5-methyl-6-phenylamino-1,4-benzoquinone 

Relevant articles and documents

Total Synthesis of (+/-)-Perezone

A total synthesis of (+/-)-perezone (1) proceeding in 18percent overall yield is described.The sequence starts from 5-bromopiperonal (2) and proceeds by way of 7, making use of an AgO-assisted oxidative dealkylation step to unmask the hydroxy-p-quinone-type system characteristic of 1.

Synthesis of Hydroxyquinones and Related Compounds: Semisquaric Acids, (+/-)-Terreic Acid, (+/-)-Perezone, and (+/-)-Isoperezone

tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-tert-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with trifluoroacetic acid at low temperature.This is a useful transformation since no reliable general route to hydroxyquinones has previously been available.The synthetic scope of this methodology as well as its specific utilization in the synthesis of a semisquaric acid, and the natural products, (+/-)-terreic acid, (+/-)-perezone, and (+/-)-isoperezone, are described.