112423-35-5

Usage

General Description

2(3H)-Furanone, dihydro-4-phenyl-5-(2-propenyl)-, trans- is an organic compound with the molecular formula C13H14O2. It is a furanone derivative, with a trans-configuration of the double bond between the carbon atoms. This chemical is used in the fragrance and flavor industry, often adding a sweet, caramel-like aroma to various products. It is also found in natural sources such as strawberries and raspberries, contributing to their characteristic scent and flavor. Additionally, 2(3H)-Furanone, dihydro-4-phenyl-5-(2-propenyl)-, trans- has been studied for its potential pharmaceutical applications, including its antimicrobial and antioxidant properties.

Upstream product

• 78920-22-6 5-hydroxy-4-phenyl-4,5-dihydro-3H-furan-2-one 
• 762-72-1 allyl-trimethyl-silane 
• 51212-29-4 β-formylbenzenepropanoic acid methyl ester 
• 106-95-6 allyl bromide 

Relevant academic research and scientific papers

On the stereoselectivity of γ-lactol substitutions with allyl- and propargylsilanes - Synthesis of disubstituted tetrahydrofuran derivatives

Monosubstituted γ-lactols 1a-1c, 3a-3c and 4a-4c, as well as disubstituted γ-lactol 5 and the γ-hydroxy-substituted γ-lactone 6, were transformed into disubstituted tetrahydrofuran derivatives by treatment with allyl- and propargylsilanes in the presence of Lewis acids. The diastereoselectivities were moderate to excellent and are interpreted by application of the Felkin-Anh model to cyclic oxocarbenium ions. The effects of the equilibria between conformers of the intermediates are discussed. The surprisingly high diastereoselectivity of 4-substituted γ-lactols 3 can be explained on this basis.

A Chelate-Controlled Route to Disubstituted and Tetrasubstituted γ-Lactones Stereoselectivity in Lewis Acid Promoted Additions to Chiral Methyl β-Formylcarboxylates

On reaction with allyltrimethylsilane/TiCl4, chiral methyl β-formylcarboxylates 1a - 1h provide disubstituted and tertasubstituted γ-lactones 3a - 3h with moderate to excellent diastereoselectivities.Other Lewis acids are less selective.The formation of seven-membered ring chelates 1.TiCl4 has been proven unambiguously by NMR spectroscopy in several cases.Trichloromethyltitanium displays a selectivity pattern similar to the reagent combination allylsilane/TiCl4.Aldehydes 1a - 1d, 1g, and 1h give primarily trans-γ-lactones, whereas under appropriate conditions 1f affords an excess of cis-γ-lactone 3f.These results are discussed with regard to the Felkin-Anh model and to chelate formation.Model studies with simpler chiral aldehydes 5 and 7 as well as with acetals 9a/b and 11a/b are presented and discussed.They emphasize the importance of chelate control in additions to β-formyl esters 1. - Key Words: γ-Lactones, di- and tetrasubstituted / Chelates, seven-membered / Allylsilane additions, Lewis acid promoted / Felkin-Anh model / Aldehydes, chiral

Radical Additions in Aqueous Medium: Direct Synthesis of 5-Allyl-Substituted γ-Lactones from Allylic Bromides/Zinc and Methyl γ-Oxocarboxylates

Following a procedure published by Luche, 5-allyl-substituted γ-lactones 2a - 2d are prepared in good yield from methyl γ-oxocarboxylates 1a - 1c and allyl bromides/zinc dust in aqueous medium.The diastereoselectivity of this allylation reaction is compared to that of Lewis acid promoted additions of allyltrimethylsilane to chiral aldehydes. - γ-Lactones; Radical additions; Felkin-Anh model