26613-71-8

Basic information

• Product Name: 3-methylidene-5-phenyldihydrofuran-2(3H)-one
• Synonyms: 3-Methylene-5-phenyldihydro-2(3H)-furanone
• CAS NO: 26613-71-8
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 174.1959
• Mol File: 26613-71-8.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 328.2°C at 760 mmHg
• Flash Point: 135.6°C
• Density: 1.14g/cm³
• Vapor Pressure: 0.000192mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: 3-methylidene-5-phenyldihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylidene-5-phenyldihydrofuran-2(3H)-one(26613-71-8)
• EPA Substance Registry System: 3-methylidene-5-phenyldihydrofuran-2(3H)-one(26613-71-8)

Safety Data

• Hazardous Substances Data: 26613-71-8(Hazardous Substances Data)

Upstream product

• 6005-95-4 acide tetrahydro-2-oxo-5-phenylfurane-3-carboxylique 
• 87763-90-4 3-bromo-1-phenyl-but-3-en-1-ol 
• 13007-90-4 bis(triphenylphosphine)nickel⁽⁰⁾ dicarbonyl 
• 109907-81-5 ethyl 4-hydroxy-2-methylene-4-phenylbutanoate 
• 112601-93-1 2-Methylene-4-phenyl-4-trimethylsilanyloxy-butyronitrile 
• 75366-42-6 4-Methoxy-2-methylene-4-phenyl-butyric acid ethyl ester 
• 87044-52-8 1-Phenyl-3-(tetrahydro-pyran-2-yloxymethyl)-but-3-en-1-ol 
• 98351-71-4 4-hydroxy-N-(α-methylbenzyl)-2-methylene-4-phenyl-butanamide 
• 95905-50-3 3-Benzenesulfonylmethyl-5-phenyl-dihydro-furan-2-one 
• 10029-04-6 ethyl 2-(hydroxymethyl)acrylate 
• 100-52-7 benzaldehyde 
• 72707-66-5 2-(bromomethyl)acrylic acid 
• 133285-88-8 ethyl 2-(methoxycarbonyloxymethyl)acrylate 
• 1064188-21-1 ZnBrCH₂C(CH₂)COOC₂H₅ 

Downstream Products

• 109958-04-5 (4S)-2-methylene-4-phenyl-γ-butyrolactone 
• 1038783-21-9 (R)-4-hydroxy-N,N-dimethyl-2-methylidene-4-phenylbutanamide 
• 130856-90-5 (3R,5S)-3-methyl-5-phenyl-4,5-dihydrofuran-2(3H)-one 
• 94540-79-1 (E)-α-benzylidene-γ-phenyl-γ-butyrolactone 

Relevant articles and documents

Reactivity of functionalized allyltrihalostannanes: An easy entry to α-methylene-γ-lactones

Stable ester monoallyltin halides 2 are prepared in excellent yields and react easily with aldehydes and ketones under very mild conditions, to provide a usefull access to various α- methylene-γ-lactones.

REFORMATSKY-TYPE REACTIONS IN AQUEOUS MEDIA. USE OF BROMOMETHYLACRYLIC ACID FOR THE SYNTHESIS OF α-METHYLENE-γ-BUTYROLACTONES.

A new method for the preparation of α-methylene-γ-butyrolactones is described.

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

Synthesis and QSAR study of novel α-methylene-γ-butyrolactone derivatives as antifungal agents

Thirty-six new α-benzylidene-γ-lactone compounds based α-methylene-γ-butyrolactone substructure were prepared and characterized by spectroscopic analysis. All compounds were evaluated for antifungal activities in vitro against six plant pathogenic fungi and the half maximal inhibitory concentration (IC50) against Botrytis cinerea and Colletotrichum lagenarium were investigated. Compounds 5c-3 and 5c-5 with the halogen atom exhibited excellent fungicidal activity against B. cinerea (IC50?=?22.91, 18.89?μM). The structure-activity relationships (SARs) analysis indicated that the derivatives with electron-withdrawing substituents at the meta- or para-positions improves the activity. Via the heuristic method, the generated quantitative structure-activity relationship (QSAR) model (R2?=?0.961) revealed a strong correlation of antifungal activity against B. cinerea with molecular structures of these compounds. Meanwhile, the cytotoxicity of 20 representative derivatives was tested in the human tumor cells line (HepG2) and the hepatic L02 cells line, the result indicated that the synthesized compounds showed significant inhibitory activity and limited selectivity. Compound 5c-5 has the highest fungicidal activity with IC50?=?18.89?μM (against B. cinerea.) but low cytotoxicity with IC50?=?35.4?μM (against HepG2 cell line) and IC50?=?68.8?μM (against Hepatic L02 cell line). These encouraging results can be providing an alternative, promising use of α-benzylidene-γ-lactone through the design and exploration of eco-friendly fungicides with low toxicity and high efficiency.

Catalytic, nucleophilic allylation of aldehydes with 2-substituted allylic acetates: Carbon-carbon bond formation driven by the water-gas shift reaction

The ruthenium-catalyzed allylation of aldehydes with allylic acetates has been expanded to incorporate substituents at the 2-position of the allylic components. Allylic acetates bearing a variety of substituents (CO 2-t-Bu, COMe, Ph, CH(OEt)su