6283-72-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(5-oxotetrahydrofuran-2-yl)propanoic acid is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the creation of complex chemical structures that can be utilized in developing new drugs.
Used in Organic Synthesis:
3-(5-oxotetrahydrofuran-2-yl)propanoic acid is used as a building block in organic synthesis for its potential to form more complex chemical structures, which can be applied in the development of novel organic compounds.
Used in Medicinal Chemistry Research:
3-(5-oxotetrahydrofuran-2-yl)propanoic acid is used as a subject of interest in medicinal chemistry and drug development research due to its potential pharmacological and biological properties, which may lead to the discovery of new therapeutic agents.

Upstream product

• 3920-53-4 heptane-1,4,7-triol 
• 98611-87-1 3-(5-oxo-tetrahydro-furan-2-yl)-propionic acid ethyl ester 
• 6317-49-3 4-oxopimelate 
• 591-80-0 pent-4-enoic acid 
• 64-69-7 Iodoacetic acid 
• 144-48-9 iodacetamide 
• 99393-08-5 R-(+)-dietilester dell'acido γ-butirrolatton-γ-metilenmalonico 
• 99393-07-4 S-(-)-dietilester dell'acido γ-butirrolatton-γ-metilenmalonico 
• 99393-06-3 R-(-)-γ-bromomethylene-γ-butyrolactone 
• 99393-05-2 S-(+)-γ-bromomethylene-γ-butyrolactone 
• 58879-33-7 (R)-(-)-γ-<(tosyloxy)methyl>-γ-butyrolactone 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 99438-12-7 R-(+) etilestere dell'acido γ-butirrolatton-γ-3-propionico 

Downstream Products

• 15889-98-2 (+/-)-methyl γ-butyrolactone-γ-propionate 
• 119627-09-7 N-[2-Phenylethyl]-2,3,4,5-tetrahydro-5-oxo-2-furanpropanamide 
• 67114-38-9 (S)-(-)-γ-jasmolactone 
• 155682-86-3 (R)-(+)-γ-jasmolactone 
• 63095-33-0 γ-(Z)-dec-7-enlactone 

Relevant academic research and scientific papers

Intramolecular acylative ring-switching reactions of 3-(tetrahydro-2′-furyl)propanoic acid derivatives to give butanolides: Mechanism and scope

The mechanisms by which dihydro-5-(3′-trifluoroacetoxypropyl)-2(3H)-furanone is formed when 3-(tetrahydro-2′- furyl)propanoic-trifluoroacetic mixed anhydride is treated with an acidic catalyst is defined, and routes to some potentially useful butanolide synthons are described.

Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenes with a water-soluble radical initiator in aqueous media: Facile synthesis of γ-lactones

Radical reactions in water or aqueous ethanol using a water-soluble radical initiator are described. Heating a mixture of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4′-azobis 4-cyanopentanoic acid), afforded 5-(4-hydroxybutyl)dihydrofuran-2(3H)-one in 95% yield. The use of 2-iodoacetic acid in place of 2-iodoacetamide also gave the same γ-lactone in 93% yield. The reaction of 2-iodoacetamide with 1-octene in aqueous ethanol was initiated by 2,2′-azobis(2-methylpropanamidine) dihydrochloride to provide γ-decanolactone. Employing water as a solvent is crucial to obtain lactone in satisfactory yield.

Enantioselective synthesis of (-)-γ-jasmolactone

The title compound was prepared in seven steps starting from the commercially available 4-ketopimelic acid. The key step features an enantioselective lactonization promoted by PPL.

Titanocene-Catalyzed Reduction of Lactones to Lactols

A convenient method for the conversion of lactones to lactols is described. The hydrosilylation to lactols is carried out via air-stable titanocene difluoride or a titanocene diphenoxide precatalyst using inexpensive polymethylhydrosiloxane (PMHS) as the stoichiometric reductant. These procedures have been demonstrated with a variety of substrates and proceed in good to excellent yield.

Asymmetric Synthesis of 5- and 6-Membered Lactones from Cyclic Substrates Bearing a C2-Chiral Auxiliary

Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated.The cyclic diamide alcohols bearing a C2-chiral auxiliary, (+)--2,2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups.By the catalytic action of trifluoroacetic acid, the substrates 6a,b and 19 were smoothly converted to the lactones 7a (71percent de), 7b (97percent de), and 20 (>99percent de), the configurations of whichwere determined to be R, S, and R, respectively.A naturally occurring pheromone, (R)-(+)-5-hexadecanolide (13), was synthesized optically pure from 7b.Transition-state models for the present asymmetric lactonization were constructed according to the stereoelectronic theory proposed by Deslongchamps.The stability of the models was assessed by MM2 calculation, and the direction of asymmetric induction thus calculated coincided with the experimental results.