Synthese von bromosubstituierten Butenoliden II

“…Butenolides 1 , 3 and 5 were prepared from 3,3‐dimethylacrylic acid ( I ),16–18 as outlined in Scheme . 3,3‐Bis(bromomethyl)acrylic acid ( II ) was obtained in 65–70% yield by reaction of I with N ‐bromosuccinimide and benzoyl peroxide under reflux in carbon tetrachloride.…”

Section: Methodsmentioning

confidence: 99%

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

Crotti

Bronze‐Uhle²,

Nascimento³

et al. 2009

J. Mass Spectrom.

View full text Add to dashboard Cite

Fragmentation reactions of beta-hydroxymethyl-, beta-acetoxymethyl- and beta-benzyloxymethyl-butenolides and the corresponding gamma-butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) using collision-induced dissociation (CID). This study revealed that loss of H(2)O [M+H-8](+) is the main fragmentation process for beta-hydroxymethylbutenolide (1) and beta-hydroxymethyl-gamma-butyrolactone (2). Loss of ketene ([M+H-42](+)) is the major fragmentation process for protonated beta-acetoxymethyl-gamma-butyrolactone (4), but not for beta-acetoxymethylbutenolide (3). The benzyl cation (m/z 91) is the major ion in the ESI-MS/MS spectra of beta-benzyloxymethylbutenolide (5) and beta-benzyloxymethyl-gamma-butyrolactone (6). The different side chain at the beta-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.

show abstract

“…In addition, it was also found able to inhibit the QS regulated bioluminescence of Vibrio harveyi BB120 with an IC 50 of 1.357 µM [109]. In 1976, 5-bromo-4-methyl-2(5H)-furanone (172) was prepared in 89% yield by reacting 4-methyl-2(5H)furanone (171) with 1.08 equiv of NBS in CCl 4 under reflux and irradiation with a 100 W lamp (Scheme 59) [113]. Scheme 59.…”

Section: Scheme 49 Total Synthesis Of Bromobeckerelide (131) Startinmentioning

confidence: 99%

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Rossi

Lessi

Manzini

et al. 2017

COC

View full text Add to dashboard Cite

This review deals with the synthesis of unnatural and natural 2(5H)-furanone derivatives featuring bromine atoms on the heterocyclic ring and/or brominated substituents, which have been described in the literature since 1951 up to February 2016. The review has been organized on the basis of six classes of brominated furanone derivatives that were synthesized: i) 2(5H)-furanone derivatives with one bromine atom on the heterocyclic ring; ii) 2(5H)-furanone derivatives with two bromine atoms on the heterocyclic ring; iii) 2(5H)-furanone derivatives featuring one bromine atom on the heterocyclic ring and monobrominated substituents; iv) 2(5H)- furanone derivatives featuring one bromine atom on the heterocyclic ring and dibrominated substituents; v) 2(5H)-furanone derivatives with monobrominated substituents; and vi) 2(5H)-furanones featuring dibrominated substituents. Where possible, experimental details of the syntheses have been reported. Furthermore, the biological properties of the target compounds, including their mutagenic, cytotoxic, enzymatic, anti-inflammatory and photosynthetic inhibitory activities have been summarized, paying particular attention on the compounds that have demonstrated antimicrobial properties via inhibition of quorum sensing and biofilm formation

show abstract

Synthese von bromosubstituierten Butenoliden II

Cited by 20 publications

References 5 publications

Stereospecific syntheses of both diastereomers of (.+-.)-2-amino-4-methyl-5-hexenoic acid

Stereospecific syntheses of both diastereomers of (.+-.)-2-amino-4-methyl-5-hexenoic acid

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

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Contact Info

Product

Resources

About