30434-70-9

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,4-Tetramethylcyclopent-2-enone is used as a chemical intermediate for the synthesis of pharmaceutical compounds, leveraging its unique structure to contribute to the development of new drugs.
Used in Fragrance Industry:
In the fragrance industry, 2,3,4,4-Tetramethylcyclopent-2-enone is used as a component in creating complex scent profiles, capitalizing on its distinctive aromatic properties to enhance or modify fragrances.
Used in Flavor Industry:
2,3,4,4-Tetramethylcyclopent-2-enone serves as a flavoring agent, employed for its taste-modifying capabilities, to add depth and complexity to various food and beverage products.

Upstream product

• 109892-46-8 3-methyl-crotonic acid sec-butyl ester 
• 625-35-4 trans-chrotonyl chloride 
• 78-78-4 methylbutane 
• 10487-71-5 crotonyl chloride 
• 131246-85-0 2-Methyl-5-trimethylsilylmethyl-2,6-heptadien-4-one 
• 6938-31-4 2-Methyl-butylcrotonat(+) 
• 30434-72-1 3,4,4,5-tetramethyl-cyclopent-2-enone 

Downstream Products

• 30221-54-6 Tetramethyl-2,3,4,4-cyclopenten-2-thion-1 

Relevant academic research and scientific papers

Stereoselective synthesis of the obscure mealybug pheromone by hydrogenation of a tetrasubstituted alkene precursor

An improved diastereoselective synthesis of (1R,2R,3S)-1-acetoxymethyl-2,3, 4,4-tetramethylcyclopentane 1, the sex pheromone of the obscure mealybug, Pseudococcus viburni, is described. The key step was diastereoselective catalytic hydrogenation of the tetrasubstituted double bond in 2,3,4,4-tetramethyl-cyclopent-2-enone 4 to give the thermodynamically less favored cis-2,3,4,4-tetramethyl-cyclopentanone 3a.

Acylation of alkenes generated in situ by hydride transfer from isoalkanes. Synthesis of pentalenones, hydrindenones, and cyclopentenones

Acylation, in the presence of AlCl3 and hydride acceptor, of methylcyclopentane, methylcyclohexane, and 2-methylbutane by ethylenic acyl chlorides, in CH2Cl2 solution, respectively, leads to tetrahydropentalenones, tetrahydroindenones, and cyclopentenones in good yields. Hydride acceptor may be either acetyl chloride or the alkenoyl chloride itself. Better results are performed in the presence of nitromethane and CuSO4. Overall yields are better than those obtained by the two-step process involving acylation of alkenes by alkenoyl chlorides and subsequent Nazarov cyclization of the resulting divinylketones. Methyl 1,4-migration is observed during the acylation of 2-methylbutane by sorboyl chloride. The mechanism of these conversions is discussed on the basis of results observed with cyclohexane-d12 and methylbutane-d6 as well as stereochemical studies of the cyclization process.

1,2-Acyl migration from β-acyl-γ-trimethylsilyl carbenium ion

TiCl4 induced rearrangement of α-allyl α′-vinylβ-trimethylsilyl ketones 3c,d,c,g leads to rearranged α-allyl α′-vinyl ketones 4c, d, e or 2-vinylcyclopentanone 9 resulting of an acyl shift with silyl control.