5443-09-4

Basic information

• Product Name: 3-(furan-2-ylmethylidene)dihydrofuran-2(3H)-one
• CAS NO: 5443-09-4
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.158
• Mol File: 5443-09-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 338.2°C at 760 mmHg
• Flash Point: 158.4°C
• Density: 1.294g/cm³
• Vapor Pressure: 9.96E-05mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 3-(furan-2-ylmethylidene)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(furan-2-ylmethylidene)dihydrofuran-2(3H)-one(5443-09-4)
• EPA Substance Registry System: 3-(furan-2-ylmethylidene)dihydrofuran-2(3H)-one(5443-09-4)

Safety Data

• Hazardous Substances Data: 5443-09-4(Hazardous Substances Data)

Upstream product

• 24349-80-2 (Z)-4,5-dihydro-3-(p-tolylsulfonyloxymethylene)-2(3H)-furanone 
• 81745-86-0 2-furylzinc chloride 
• 98-01-1 furfural 
• 5061-21-2 α-bromo-γ-butyrolactone 
• 547-65-9 α-methylene-γ-butyrolactone 
• 57899-27-1 (E)-4,5-dihydro-3-(p-tolylsulfonyloxymethylene)-2(3H)-furanone 
• 66909-41-9 O-ethyl S-(tetrahydro-2-oxo-3-furanyl) thiocarbonate 
• 14032-62-3 2-mercapto-γ-butyrolactone 
• 34932-07-5 3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone 
• 96-48-0 4-butanolide 

Relevant articles and documents

Bioactivity-guided mixed synthesis and evaluation of α-alkenyl-γ and δ-lactone derivatives as potential fungicidal agents

In view of the great antifungal activities of sesquiterpene lactones and natural product Tulipalin A, 52 derivatives derived from α-methylene-γ-butyrolactone substructures were synthesized to study antifungal activities. In vitro and in vivo antifungal activity results revealed that compounds 2-25, which contain a γ-butyrolactone scaffold and cinnamic aldehyde moiety, have greater potent fungicidal activity than other compounds. The preliminary structure-activity relationships (SARs) demonstrated that compounds with electron-withdrawing groups and small steric hindrance would have more desirable potency. Meanwhile, the quantitative structure-activity relationship (QSAR) model (R2 = 0.947, F = 65.77, and S2 = 0.0028) revealed a convincing correlation of antifungal activity against B. cinerea with molecular structures of title compounds. The present study provided a more detailed insight into the antifungal activity of the α-methylene-γ-butyrolactone substructure, which provided a potential expectation for the exploration of α-alkenyl-γ-butyrolactone structures in agriculture.

Breaking the ring through a room temperature catalytic wittig reaction

One ring no longer rules them all: Employment of 2.5-10 mol % of 4-nitrobenzoic acid with phenylsilane led to the development of a room temperature catalytic Wittig reaction (see scheme). Moreover, these enhanced reduction conditions also facilitated the use of acyclic phosphine oxides as catalysts for the first time. A series of alkenes were produced in moderate to high yield and selectivity. Copyright

Stereoselective synthesis of α-alkylidene- and substituted alkylidene- γ-lactones

Cross-coupling reactions of (E)- and (Z)-tosylates of α- hydroxymethylene-γ-butyrolactone with aryl, heteroaryl, alkyl, and alkynylzinc chlorides under Pd(PPh3)4 catalysis were found to be a suitable synthetic method for stereoselective preparation of α-alkylidene- and substituted alkylidene-γ-lactones. The reactions, conducted under mild conditions, proceed with high stereoselectivity and moderate yields. (C) 2000 Elsevier Science Ltd.