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

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.

A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones

Combining biological and small-molecule catalysts under a chemoenzymatic manifold presents a series of significant advantages to the synthetic community. We report herein the successful development of a two-step/single flask synthesis of γ-lactones through the merger of Umpolung catalysis with a ketoreductase-catalyzed dynamic kinetic resolution, reduction, and cyclization. This combined approach delivers highly enantio- and diastereoenriched heterocycles and demonstrates the feasibility of integrating NHC catalysis with enzymatic processes.

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.

Stereoselective synthesis of trans-β-methoxycarbonyl-γ-aryl-γ-butyrolactones

Stereoselective synthesis of trans-β-methoxycarbonyl-γ-aryl-γ-butyrolactones (5) by the reaction of methoxycarbonylmethyl triphenyl arsonium bromide (1) and 2,2-dimethyl-5-substituted-benzal-1,3-dioxa-4,6-dioxa-4,6-dione (2) is carried out in the presence

Trimethylsilyl Cyanide - A Reagent for Umpolung, XX. - On the Regioselectivity of the Addition of Carbonyl Compounds to α,β-Unsaturated Aldehydes after Umpolung

By addition of tBuMe2SiCN to α,β-unsaturated aldehydes 5 the silylated cyanohydrins 6 are produced.Deprotonation of 6 provides allylic anions which can be attached to aldehydes and ketones in α-position (kinetic control) (-> 8) or γ-position (thermodynamic control) (-> 9).In contrast to the Me3Si group which has been applied so far the tBuMe2Si group is stable under the reaction conditions.Therefore, the ratio of α/γ adducts can be tuned from > 95:5 to 5:95 depending on the substitution pattern of 6, the aldehydes and ketones, the reaction time and temperature, and even by some additives.The γ adducts 9 are easily transformed into γ-butyrolactones 27 by acidic hydrolysis. Key Words: Umpolung / Regioselectivity / Substituent effects / Acylation, nucleophilic / Aldehydes, α,β-unsaturated / Trimethylsilyl cyanide

Manganese(III)-Mediated γ-Lactone Annulation

The annulation of a γ-lactone ring onto an alkene by manganese(III) acetate oxidation of acetic acid was investigated.The regioselectivity of addition to unsymmetrically substituted alkenes is reported along with the stereoselectivity of addition to various acyclic and cyclic alkenes.Alkenes with ionization potentials above 8.2 eV were found to react in good yield.The role of acetic anhydride in these reactions was studied, and it was shown to be oxidized faster than acetic acid and also led to different products.The fate of oxidized acetic acid or anhydridein the absence of suitable acceptor molecule has also been quantitatively identified.The relationship of enolizability, or C-H acidity, of the carboxylic acid being oxidized was established quantitatively.