61934-55-2

Usage

Uses

Used in Organic Chemistry:
4-(Bromomethyl)-5-hydrofuran-2-one is used as a reagent for various chemical reactions due to its unique structure and properties. The presence of bromine in the compound allows for a wide range of applications in organic synthesis, where it can act as an intermediate or a building block for more complex molecules.
Used in Biochemistry Research:
In the field of biochemistry, 4-(Bromomethyl)-5-hydrofuran-2-one is employed as a research tool to study the interactions and reactions of biomolecules. Its structure enables it to be used in the development of new biochemical assays and as a probe to understand the mechanisms of certain biological processes.
Used in Pharmaceutical Development:
4-(Bromomethyl)-5-hydrofuran-2-one is used as a starting material or a key intermediate in the synthesis of pharmaceutical compounds. Its versatility in chemical reactions allows for the creation of new drug candidates, potentially leading to the development of novel therapeutic agents.
Used in Material Science:
In material science, 4-(Bromomethyl)-5-hydrofuran-2-one is utilized in the synthesis of new materials with specific properties. Its chemical structure can be incorporated into polymers, coatings, or other materials to impart unique characteristics, such as improved stability, reactivity, or selectivity.
Used in Analytical Chemistry:
4-(Bromomethyl)-5-hydrofuran-2-one is used as an analytical reagent in various analytical techniques. Its chemical properties can be exploited to develop new methods for the detection, quantification, or separation of different compounds, enhancing the sensitivity and accuracy of analytical procedures.

InChI:InChI=1/C5H5BrO2/c6-2-4-1-5(7)8-3-4/h1H,2-3H2

Upstream product

• 75887-43-3 4-bromo-3-(bromomethyl)but-2-enoic acid 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 922500-91-2 ethyl 2-(oxetan-3-ylidene)acetate 
• 541-47-9 3-Methylbutenoic acid 
• 5687-73-0 2-cyclopropylideneacetic acid 
• 74592-36-2 ethyl cyclopropenylideneacetate 

Downstream Products

• 64190-48-3 dihydro-4-methyl-2(3H)-furanone 
• 6124-79-4 4-methyl-2(5H)-furanone 
• 125973-99-1 4-(Chloromethyl)-2(5H)-furanone 
• 94807-93-9 (S)-3-methyl-4-phenylthio-1-butanol 
• 145930-15-0 (+)-(R)-3-phenylthiomethylbutanolide 
• 133435-76-4 4-(benzyloxymethyl)-2(5H)-furanone 
• 145930-14-9 3-phenylsulfinylmethyl-2-butenolide 
• 145930-16-1 (+)-(3R)-3-phenylsulfinylmethylbutanolide 
• 145930-18-3 (R)-3-Hydroxymethyl-4-phenylsulfanyl-butyric acid methyl ester 
• 172796-28-0 (R)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one 
• 133435-77-5 (S)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one 
• 80367-72-2 (E,E,E)-4-<4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatrienyl>-2(5H)-furanone 
• 1309690-00-3 C₁₃H₁₃NO₂S₂ 
• 1309689-99-3 C₁₂H₁₁NO₂S₂ 

Relevant academic research and scientific papers

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

The selective ring-opening reaction of fluoroalkylidene-oxetanes was directed by the presence of the fluorine atom, enabling a two-step access to tetrasubstituted fluoroalkenes with excellent geometry control. Despite its small van der Waals radii electronic, rather than steric influences of the fluorine atom governed the ring-opening reaction with bromide ions, even in the presence of bulky substituents.

Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin

Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright

Photochemical reactions of prop-2-enyl and prop-2-ynyl substituted 4-aminomethyl- and 4-oxymethyl-2(5H)-furanones

Compounds with a heterocyclic 9-oxatricyclo[5.3.0.01,5]decan-8-one skeleton were synthesized by intramolecular [2+2] photocycloaddition reactions of the title compounds (λ= 254 nm, Et2O or MeCN as the solvent). Starting from various substituted 4-(prop-2-enylaminomethyl)-2(5H)-furanones, products 5, 9, 18, 21, 23, 24 were obtained, which bear a nitrogen atom in position 3 of this skeleton within a pyrrolidine ring. The Boc or Cbz groups represent suitable nitrogen protecting groups, which were compatible with the irradiation conditions and which can be easily cleaved. In an analogous fashion an oxygen (product 22) and carbon substituent (product 25) could be implemented at position 3 of the product if the starting material was appropriately chosen. The prop-2-ynyl substituted substrates did not produce a [2+2] photocycloaddition product but rather underwent a cyclization to spiro products 11 and 13.

Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions

Intramolecular [2+2] photocycloaddition reactions of diversely substituted N-Boc protected 4-(allylaminomethyl)-2(5H)-furanones resulted in rigid products (53-75%) with three spatially defined positions for further functionalisation. The Royal Society of Chemistry.

Triazole-dithiocarbamate based selective lysine specific demethylase 1 (LSD1) inactivators inhibit gastric cancer cell growth, invasion, and migration

Lysine specific demethylase 1 (LSD1), the first identified histone demethylase, plays an important role in epigenetic regulation of gene activation and repression. The up-regulated LSD1's expression has been reported in several malignant tumors. In the cu

Substituted pyrazolones require N2 hydrogen bond donating ability to protect against cytotoxicity from protein aggregation of mutant superoxide dismutase 1

Amyotrophic lateral sclerosis (ALS) is a debilitating and fatal neurodegenerative disease. Although the cause remains unknown, misfolded protein aggregates are seen in neurons of sporadic ALS patients, and familial ALS mutations, including mutations in su

Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates

Three series of butenolide-containing dithiocarbamates were designed and synthesized. Their anti-tumor activity in vitro was evaluated. Among them compound I-14 exhibited broad spectrum anti-cancer activity against five human cancer cell lines with IC50 30 μM. Structure-activity relationship analysis showed that the introduction of dithiocarbamate side chains on the C-3 position of butenolide was crucial for anti-tumor activity.

Stereoselective synthesis of desloratadine derivatives as antagonist of histamine

A series of desloratadine derivatives were stereoselectively synthesized and evaluated for H1 antihistamine activity. For the evaluation of H1 antihistamine activity, the in vitro histamine-induced contraction of the guinea-pig ileum assay (HC) was used. The synthesized desloratadine derivatives 7, 8 and 9 are structurally related to rupatadine and were generated by replacement of the 5-methyl-3-pyridine group of rupatadine with γ-alkylidene butenolide. Their H1 antihistamine activities have shown a high dependence on the exact nature of the substituent in the lactone ring. Optimum structures 7, 8a and 8g display potent activity inhibiting histamine-induced effects.

Gas-phase fragmentation of γ-lactone derivatives by electrospray ionization tandem mass spectrometry

Fragmentation reactions of β-hydroxymethyl-, β-acetoxymethyl- and β-benzyloxymethyl-butenolides and the corresponding γ-butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) using collision-induced dissociation (CID). This study revealed that loss of H2O [M+H-18]+ is the main fragmentation process for β-hydroxymethylbutenolide (1) and β-hydroxymethyl-γ- butyrolactone (2). Loss of ketene ([M+H-42]+) is the major fragmentation process for protonated β-acetoxymethyl-γ-butyrolactone (4), but not for β-acetoxymethylbutenolide (3). The benzyl cation (m/z 91) is the major ion in the ESI-MS/MS spectra of β-benzyloxymethylbutenolide (5) and β-benzyloxymethyl-γ-butyrolactone (6). The different side chain at the β-position and the double bond presence afforded some product ions that can be important for the structural identification of each compound. The energetic aspects involved in the protonation and gas-phase fragmentation processes were interpreted on the basis of thermochemical data obtained by computational quantum chemistry. Copyright

Facile and Effective Copper-Mediated Cyclization Reaction of Cyclopropylideneacetic Acids (or Esters) and Cyclopropylideneacetonitriles

The full details of the copper-mediated cyclization reaction of cyclopropylideneacetic acids (or esters) and cyclopropylidenenitriles, the synthetic application of this reaction, and the study of the reaction mechanism are reported.