13389-99-6

Basic information

• Product Name: methyl 5-oxo-2-phenyltetrahydrofuran-3-carboxylate
• Synonyms: 5-Oxo-2-phenyltetrahydro-3-furoic acid methyl ester;3-Furoic acid, tetrahydro-5-oxo-2-phenyl-, methyl ester
• CAS NO: 13389-99-6
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.2213
• Mol File: 13389-99-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 380.1°C at 760 mmHg
• Flash Point: 196°C
• Density: 1.236g/cm³
• Vapor Pressure: 5.6E-06mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: methyl 5-oxo-2-phenyltetrahydrofuran-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-oxo-2-phenyltetrahydrofuran-3-carboxylate(13389-99-6)
• EPA Substance Registry System: methyl 5-oxo-2-phenyltetrahydrofuran-3-carboxylate(13389-99-6)

Safety Data

• Hazardous Substances Data: 13389-99-6(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 150-90-3 sodium succinate 
• 100-52-7 benzaldehyde 
• 103-26-4 Methyl cinnamate 
• 64-19-7 acetic acid 
• 38330-80-2 monomethyl monopotassium malonate 
• 1214-54-6 5-benzylidene Meldrum's acid 
• 1529-78-8 [(methoxycarbonyl)methyl]triphenylarsonium bromide 
• 141-82-2 malonic acid 
• 624-49-7 dimethylfumarate 
• 143635-21-6 4-Cyan-2-(1'-phenyl-1'-trimethylsilyloxymethyl)-4-trimethylsilyloxy-3-butensaeure-methylester 
• 81040-02-0 (Z)-4-Cyan-4-(trimethylsilyloxy)-3-butensaeure-methylester 

Relevant articles and documents

Mn(III)-promoted synthesis of functionalized γ-lactones in acetic and formic acids

The yield of substituted γ-lactones obtained by Mn(III)-mediated addition of potassium monomethyl malonate on cinnamate esters can be optimized by performing the reaction either in acetic or in formic acid, depending on the substrate.

Formation of γ-lactones through CAN-mediated oxidative cleavage of hemiketals

(Chemical Equation Presented) The generation of substituted γ-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an α-heteroatom. Formation of the γ-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products.

Efficient MnIII-mediated synthesis of functionalized trans-3,4-disubstituted-γ-butyrolactones

The MnIII-induced addition of malonic acid (instead of acetic acid) to cinnamic esters affords in one step functionalized trans-3,4-disubstituted-γ-butyrolactones in a greatly improved yield which can be further optimized by conducting the reaction in either acetic or formic acid, depending on the substrate.