1775-46-8

Usage

Uses

Used in Organic Synthesis:
Pentanoic acid, 3,5-dibromo-4-oxo is used as a building block in organic synthesis for the creation of various chemical compounds. Its unique properties, including the presence of bromine atoms and a ketone group, make it a valuable intermediate in the synthesis of complex organic molecules.
Used in Chemical Research:
Pentanoic acid, 3,5-dibromo-4-oxo is utilized as a research compound in chemical studies to explore its reactivity and potential applications. Its unique structure allows researchers to investigate its interactions with other molecules and its role in various chemical reactions.
Used in Pharmaceutical Industry:
Pentanoic acid, 3,5-dibromo-4-oxo may have potential applications in the pharmaceutical industry as a precursor for the development of new drugs. Its unique properties and reactivity could be harnessed to create novel therapeutic agents. However, further research is needed to fully understand its potential and safety in this context.
Used in Industrial Applications:
Pentanoic acid, 3,5-dibromo-4-oxo may also have potential uses in various industrial applications, such as the production of specialty chemicals, materials, or coatings. Its unique properties could be leveraged to develop new products or improve existing ones. Further studies are required to assess its suitability and performance in these applications.

InChI:InChI=1/C5H6Br2O3/c6-2-4(8)3(7)1-5(9)10/h3H,1-2H2,(H,9,10)/t3-/m1/s1

Upstream product

• 123-76-2 levulinic acid 
• 7732-18-5 water 
• 10035-10-6 hydrogen bromide 
• 7726-95-6 bromine 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 

Downstream Products

• 32323-47-0 (5Z)-4-bromo-5-(bromomethylene)-2-(5H)-furanone 
• 32323-44-7 5-(dibromomethylene)-2(5H)-furanone 
• 360783-23-9 (Z)-5-(bromomethylene)furan-2-(5Η)-one 
• 923-06-8 bromosuccinic acid 
• 2973-00-4 dibromo-dinitro-methane 
• 144-62-7 oxalic acid 
• 110-17-8 (2E)-but-2-enedioic acid 
• 431-03-8 dimethylglyoxal 
• 35304-86-0 (Z)-5-phenyl-2,4-pentadien-4-olide 
• 35304-87-1 (E)-4-benzylidene-2-butenolide 
• 158071-58-0 (5Z)-5-[(E)-3-phenylallylidene]-5H-furan-2-one 
• 158071-59-1 5-[(E)-3-Phenyl-prop-2-en-(E)-ylidene]-5H-furan-2-one 
• 676556-25-5 (Z)-5-(1-bromo-1-phenylmethylene)-2(5H)-furanone 
• 676556-23-3 5-[(E)-1-Bromo-3-phenyl-prop-2-en-(Z)-ylidene]-5H-furan-2-one 

Relevant academic research and scientific papers

Mechanism-based inactivation of coenzyme B12-dependent 2-methyleneglutarate mutase by (Z)-glutaconate and buta-1,3-diene-2,3- dicarboxylate

In the presence of holo 2-methyleneglutarate mutase, buta-1,3-diene-2,3- dicarboxylate and (Z)-glutaconate [(Z)-pent-2-ene-1,5-dicarboxylate], but not (E)-glutaconate, each induced homolysis of the Co-C bond of coenzyme B 12 to afford cob(II)alamin and the 5′-deoxyadenosyl radical. The latter probably added to the double bond in (Z)-glutaconate and one of the double bonds in buta-1,3-diene-2,3-dicarboxylate to afford a corresponding "radical adduct". The formation of new radicals and cob(II)alamin was diagnosed by UV/Visible and EPR spectroscopy. (Z)-Glutaconate rapidly inactivated the mutase with formation of aquocobalamin, which was possibly derived by electron transfer from cob(II)alamin to the radical adduct. In contrast, buta-1,3-diene-2,3-dicarboxylate was a much slower inactivator. In this case, the spectroscopic data revealed a relatively stable complex of the radical adduct with cob(II)alamin in the active site of the enzyme. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Design and synthesis of aryl-substituted pyrrolidone derivatives as quorum sensing inhibitors

Quorum sensing, a common cell-to-cell communication system, is considered to have promising application in antibacterial therapy since they are expected to induce lower bacterial resistance than conventional antibiotics. However, most of present quorum sensing inhibitors have potent cell toxicity, which limits their application. In this study we evaluated the diverse quorum sensing inhibition activities of different biaromatic furanones and brominated pyrrolones. On this basis, we further designed and synthesized a new series of aryl-substituted pyrrolones 12a-12f. In the quorum sensing inhibition assay, compound 12a showed improved characteristics and low toxicity against human hepatocellular carcinoma cell. In particular, it can inhibit the pyocyanin production and protease activity of Pseudomonas aeruginosa by 80.6 and 78.5%, respectively. Besides, in this series, some compounds exerted moderate biofilm inhibition activity. To sum up, all the findings indicate that aryl-substituted pyrrolidone derivatives are worth further investigation as quorum sensing inhibitors.

Bacterial quorum sensing inhibitors as well as preparation method and application thereof

The invention provides bacterial quorum sensing inhibitors as well as a preparation method and an application thereof, and belongs to the technical field of medical chemistry. The bacterial quorum sensing inhibitors mainly comprise alpha-pyridoin derivati

Ionic liquids - Advanced reaction media for organic synthesis

The advantages in the application of ionic liquids as reaction media in organic synthesis, i.e., in the preparation of chromane derivatives, substituted pyrazines, 4-aminofuran-2(5H)-ones, or in bromination of Levulinic acid or dehydration of alcohols, saccharides, and polysaccharides, have been demonstrated on several examples. Ionic liquids with Bronsted acidity have been shown to possess catalytic activity and provide access to convenient technologies for the preparation of various useful compounds. Copyright Merck KGaA.

METHYLENE FURANONE DERIVATIVES AND USE OF SAID DERIVATIVES AS A PHOTOPROTECTING OR ANTIOXIDANT OR DEPIGMENTATION AGENT IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS

The present invention relates to novel methylene furanone derivatives as well as the use thereof as a protective, antioxidant, or depigmentation agent in cosmetic or dermatological compositions. The invention also relates to a method for preparing said derivatives involving a Suzuki-Miyaura coupling reaction from corresponding dibromofuranone derivatives. The invention also relates to a method of preparation involving a coupling reaction of 2-methoxy-furan derivatives with a ketone followed by dehydration.

Variation in the regioselectivity of levulinic acid bromination in ionic liquids

The reaction of levulinic acid and its esters with bromine in ionic liquids results in the formation of 3-bromo derivatives as the major products and not the 5-bromo substituted isomers, which are typically formed in organic solvents. The bromination of l

Stereoselective syntheses of dihydroxerulin and xerulinic acid, anti-hypocholesterolemic dyes from the fungus Xerula melanotricha

The title compounds 2 and 3, which are inhibitors of the biosynthesis of cholesterol, were synthesized in a convergent and perfectly stereoselective manner. In the key step, bromobutenolide 6 (obtained from levulinic acid in two steps) was coupled with either of the novel bis(stannanes) trans,cis, -trans-35 or trans,trans,trans-35 [each accessible from 3-(tributylstannyl)allyl alcohol (17) in four steps], giving γ-alkylidenebutenolide trans,trans,trans-32. This compound was coupled with iododiyne 42 or the bromoenediynoate 44 leading to dihydroxerulin (2) and to the (trimethylsilylethyl)ester 45 of xerulinic acid, respectively. Deprotection of the latter provided totally synthetic xerulinic acid (3) for the first time.

Total synthesis of xerulinic acid

An inhibitor of the biosynthesis of cholesterol, xerulinic acid, has been synthesized for the first time. The convergent approach applied involves the palladium-catalyzed coupling of an enediynoic ester building block, a conjunctive C6 bisstannane, and a bromine-containing methylenebutenolide (see scheme; R = Me3SiCH2CH 2).

Synthesis of cyclic compounds

A method for the preparation of a compound of formula (II) wherein R1 and R2 are independently H, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl whether unsubstituted or substituted, optionally interrupted by one or more hetero atoms, straight chain or branched chain, hydrophilic, hydrophobic or fluorophilic; R3, R4, R5 and R6 are independently or all hydrogen or halogen; provided that at least two of the R3, R4, R5 and R6 are halogens.

Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones

A synthesis of ethyl-, butyl-, hexyl- and dodecyl-substituted fimbrolides from alkyl-substituted levulinic acid derivatives through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation. occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrolides in 100% H2SO4. The formation of related beckerelide substances is also described.