362483-70-3

Basic information

• Product Name: methyl 2-(4-bromophenyl)pent-4-enoate
• Synonyms: methyl 2-(4-bromophenyl)pent-4-enoate
• CAS NO: 362483-70-3
• Molecular Weight: 269.138
• Mol File: 362483-70-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2-(4-bromophenyl)pent-4-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(4-bromophenyl)pent-4-enoate(362483-70-3)
• EPA Substance Registry System: methyl 2-(4-bromophenyl)pent-4-enoate(362483-70-3)

Safety Data

• Hazardous Substances Data: 362483-70-3(Hazardous Substances Data)

Upstream product

• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 106-95-6 allyl bromide 

Downstream Products

• 1222181-53-4 methyl 2-(4-bromophenyl)-3-(oxiran-2-yl)-propanoate 
• 188943-73-9 2-(4-bromophenyl)pent-4-enoic acid 
• 362483-84-9 3-(4-bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-dihydro-furan-2-one 
• 362483-88-3 3-(4-bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one 
• 362483-24-7 3-(4-bromophenyl)-5-hydroxymethyl-2,5-dihydrofuran-2-one 
• 362483-77-0 3-(4-bromo-phenyl)-5-hydroxymethyl-dihydro-furan-2-one 
• 301854-29-5 3-(4-bromophenyl)-5-methyltetrahydrofuran-2-one 

Relevant articles and documents

Macrocycles All Aflutter: Substitution at an Allylic Center Reveals the Conformational Dynamics of [13]-Macrodilactones

The shapes adopted by large-ring macrocyclic compounds play a role in their reactivity and their ability to be bound by biomolecules. We investigated the synthesis, conformational analysis, and properties of a specific family of [13]-macrodilactones as models of natural-product macrocycles. The features of our macrodilactones enabled us to study the relationship between stereogenic centers and planar chirality through the modular synthesis of new members of this family of macrocycles. Here we report on insights gained from a new [13]-macrodilactone that is substituted at a position adjacent to the alkene in the molecule. Analysis of the compound, in comparison to an α-substituted regioisomer, by using X-ray crystallography, NMR coupling constants, and reaction-product characterization in concert with computational chemistry, revealed that the alkene unit is dynamic. That is, the data support a model in which the alkene in our [13]-macrodilactones oscillates between two conformations. A difference in reactivity of one conformation compared to the other leads to manifestation of this dynamic behavior. The results underscore the local conformational dynamics observed in some natural-product macrocycles, which could have implications for biomolecule binding.

3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones: Synthesis and biological activity of a novel group of potential antifungal drugs

3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34 μg/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 μg/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.