34932-07-5

Basic information

• Product Name: 3-(Triphenylphosphoranylidene)tetrahydrofuran-2-one
• Synonyms: 3-(Triphenylphosphoranylidene)-4,5-dihydrofuran-2(3H)-one;3-(Triphenylphosphoranylidene)tetrahydrofuran-2-one;4,5-Dihydro-3-(triphenylphosphoranylidene)-2(3H)-furanone;2-(Triphenylphosphoranylidene)-gama-butyrolactone;3-(Triphenylphosphoranylidene)-gama-butyrolactone;Dihydro-3-(triphenylphosphoranylidene)-2(3H)-furanone;3-(Triphenylphosphoranylidene)dihydrofuran-2-(3H)-one;2-(TRIPHENYLPHOSPHORANYLIDENE)-GAMMA-BUTYROLACTONE
• CAS NO: 34932-07-5
• Molecular Formula: C₂₂H₁₉O₂P
• Molecular Weight: 346.36
• Mol File: 34932-07-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 502.1°C at 760 mmHg
• Flash Point: 270.6°C
• Appearance: White to off-white/Powder
• Density: 1.23
• Vapor Pressure: 3.26E-10mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 3-(Triphenylphosphoranylidene)tetrahydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Triphenylphosphoranylidene)tetrahydrofuran-2-one(34932-07-5)
• EPA Substance Registry System: 3-(Triphenylphosphoranylidene)tetrahydrofuran-2-one(34932-07-5)

Safety Data

• Hazardous Substances Data: 34932-07-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H19O2P/c23-22-21(16-17-24-22)25(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,16-17H2

Upstream product

• 5061-21-2 α-bromo-γ-butyrolactone 
• 603-35-0 triphenylphosphine 
• 28228-78-6 (2-oxotetrahydro-3-furanyl)triphenylphosphonium bromide 

Downstream Products

• 66909-43-1 (E)-α-(2-furylmethylene)-γ-butyrolactone 
• 85681-03-4 (E)-N⁶-Benzoyl-2',3'-O-isopropylidene-5'-C-(2-oxotetrahydro-3-furanylidene)-5'-deoxyadenosine 
• 547-65-9 α-methylene-γ-butyrolactone 
• 10008-73-8 5-methylenedihydrofuran-2-one 
• 1530-65-0 3-((Ξ)-4-nitro-benzylidene)-dihydro-furan-2-one 
• 1530-60-5 3-((Ξ)-4-acetylamino-benzylidene)-dihydro-furan-2-one 
• 1530-58-1 3-(3,4,5-trimethoxy-benzylidene)-dihydro-furan-2-one 
• 5431-89-0 3-((Ξ)-vanillylidene)-dihydro-furan-2-one 
• 52216-90-7 (E)-α-propylidene-γ-butyrolactone 
• 1530-63-8 4-(2-oxo-dihydro-furan-3-ylidenemethyl)-benzonitrile 
• 172958-84-8 (1''R)-(1'E)-3-<2'-(2'',2''-dimethyl-6''-methylene-cyclohexyl)-ethylidene>-dihydrofuran-2-one 
• 213992-76-8 3-[1-[(1R,2S,5S)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-meth-(E)-ylidene]-dihydro-furan-2-one 
• 226943-65-3 C₃₁H₄₈O₆ 
• 505904-79-0 3-(2-methoxybenzylidene)dihydrofuran-2-one 

Relevant articles and documents

Diels-Alder reactions of α-vinylidene-γ-butyrolactones

α-Vinylidene-γ-butyrolactones 2 and 4 are readily prepared via the reaction of ylides 1 or 3 with ketene. Diels-Alder cycloadditions of these compounds with typical dienes are described, addition of 2 to cyclopentadiene giving predominantly the exo stereomer.

Photoenzymatic Generation of Unstabilized Alkyl Radicals: An Asymmetric Reductive Cyclization

Flavin-dependent "ene"-reductases can generate stabilized alkyl radicals when irradiated with visible light; however, they are not known to form unstabilized radicals. Here, we report an enantioselective radical cyclization using alkyl iodides as precursors to unstabilized nucleophilic radicals. Evidence suggests this species is accessed by photoexcitation of a charge-transfer complex that forms between flavin and substrate within the protein active site. Stereoselective delivery of a hydrogen atom from the flavin semiquinone to the prochiral radical formed after cyclization provides high levels of enantioselectivity across a variety of substrates. Overall, this transformation demonstrates that photoenzymatic catalysis can address long-standing selectivity challenges in the radical literature.

A modular and scalable one-pot synthesis of polysubstituted furans

One four all: Allyl dienol carbonates can be readily converted into diversely substituted furans by a one-pot four-step sequence featuring a palladium-catalyzed decarboxylative allylic alkylation, a microwave-mediated Cope rearrangement, a nucleophilic addition, and a dehydration reaction (see scheme). The protocol is operationally simple, highly flexible, and provides di-, tri-, and tetrasubstituted furans starting from readily available materials. Copyright