3285-00-5

Basic information

• Product Name: 4-methyloctan-4-olide
• Synonyms: 4-methyloctan-4-olide;5-Butyldihydro-5-methyl-2-(3H)-furanone;5-Butyldihydro-5-methyl-3H-furan-2-one;5-Methyl-5-butyl-4,5-dihydro-2(3H)-furanone
• CAS NO: 3285-00-5
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22214
• EINECS: 221-934-7
• Mol File: 3285-00-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 235.7°Cat760mmHg
• Flash Point: 90.1°C
• Appearance: /
• Density: 0.945g/cm³
• Vapor Pressure: 0.0492mmHg at 25°C
• Refractive Index: 1.438
• CAS DataBase Reference: 4-methyloctan-4-olide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyloctan-4-olide(3285-00-5)
• EPA Substance Registry System: 4-methyloctan-4-olide(3285-00-5)

Safety Data

• Hazardous Substances Data: 3285-00-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H16O2/c1-3-4-6-9(2)7-5-8(10)11-9/h3-7H2,1-2H3

Upstream product

• 542-69-8 1-iodo-butane 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 24424-68-8 1-methyl-1-vinyl-1-pentanol 
• 201230-82-2 carbon monoxide 
• 623-48-3 ethyl iodoacetae 
• 58683-10-6 4-methyl-4S-hydroxy-1-octyne 
• 90722-02-4 1-bromo-4-methyl-oct-1-yn-4-ol 
• 591-78-6 n-hexan-2-one 
• 121802-57-1 (Z)-1-(1-Methoxymethyl-1H-imidazol-2-yl)-4,6-dimethyl-1-triisopropylsilanyloxy-hept-1-en-4-ol 
• 76569-26-1 1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole 
• 112751-92-5 4-Benzenesulfonyl-5-butyl-5-methyl-dihydro-furan-2-one 
• 693-03-8 n-butyl magnesium bromide 

Downstream Products

• 38514-03-3 4-methyloctan-1-ol 
• 72473-95-1 4-methyl-octane-1,4-diol 
• 855598-38-8 4-methyl-octanoic acid-(4-methyl-octyl ester) 
• 56196-53-3 (+/-)-Ethyl 4-methyloctanoate 

Relevant articles and documents

Radical-polar crossover reactions of vinylboron ate complexes

Vinyl boronic esters are valuable substrates for Suzuki-Miyaura cross-coupling reactions. However, boron-substituted alkenes have drawn little attention as radical acceptors, and the radical chemistry of vinylboron ate complexes is underexplored. We show here that carbon radicals add efficiently to vinylboron ate complexes and that their adduct radical anions undergo radical-polar crossover: A 1,2-alkyl/aryl shift from boron to the α-carbon sp2 center provides secondary or tertiary alkyl boronic esters. In contrast to the Suzuki-Miyaura coupling, a transition metal is not required, and two carbon-carbon bonds are formed. The valuable boronic ester moiety remains in the product and can be used in follow-up chemistry, enlarging the chemical space of the method. The cascade uses commercial starting materials and provides access to perfluoroalkylated alcohols, γ-lactones, γ-hydroxy alkylnitriles, and compounds bearing quaternary carbon centers.

Unprecedented rearrangement of a 4-alkoxy-5-bromoalk-2-en-1-ol to a cyclopentenone via an iso-nazarov cyclization process

(Chemical Equation Presented) We report the structure determination of the product 9 of the rearrangement of the allylic alcohol 3 under very mild conditions, probably promoted by an acidic substance, and propose a reasonable mechanism for its formation.

C-C Bond Cleavage of 2-Acylimidazolium Salts in a Sequence involving a New Ester Homoenolate Equivalent. A Synthesis of γ-Lactones

Reaction of the anion of 2-(1-tri-isopropylsiloxyallyl)-N-methoxymethylimidazole with ketones and aldehydes proseeds regioselectivity to give the enol silyl ethers of 2-acylimidazoles which suffer cleavage to γ-lactones after desilylation, N-methylation, and base treatment.