471-45-4

Usage

InChI:InChI=1/C2H2FIO2/c3-1(4)2(5)6/h1H,(H,5,6)

Upstream product

• 401-58-1 ethyl 2-fluoro-2-iodoacetate 
• 428-94-4 ethyl-(1,1,2-trifluoro-2-iodo-ethyl)-ether 
• 813-36-5 methyl-(1,1,2-trifluoro-2-iodo-ethyl)-ether 

Relevant academic research and scientific papers

Limitations of the Wittig-Horner-type annulation of fluorobutenolide moiety to 3-hydroxyquinoline-2,4(2H,3H)-diones. Novel modifications of the Perkow reaction including fluorinated acyloxy leaving groups

3-(Fluoroacyloxy)quinoline-2,4(1H,3H)-diones react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the leaving group. For t

Asymmetric synthesis of chiral organofluorine compounds: Use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of HIV protease inhibitors

Two stereoselective routes to a series of diastereomeric inhibitors of HIV protease, monofluorinated analogues of the Merck HIV protease inhibitor indinavir, are described. The two routes feature stereoselective construction of the fluorinated core subunits by asymmetric alkylation reactions. The first-generation syntheses were based on the conjugate addition of the lithium enolate derived-from pseudoephedrine α-fluoroacetamide to nitroalkene 12, a modestly diastereoselective transformation. A more practical second-generation synthetic route was developed that is based on a novel method for the asymmetric synthesis of organofluorine compounds, by enolate alkylation using optically active fluoroiodoacetic acid as the electrophile in combination with a chiral amide enolate. Resolution of fluoroiodoacetic acid with ephedrine provides either enantiomeric form of the electrophile in ≥96% ee. Alkylation reactions with this stable and storable chiral fluorinated precursor are shown to proceed in a highly stereospecific manner. With the development of substrate-controlled syn- or anti-selective reductions of α-fluoro ketones 44 and 45 (diastereomeric ratios 12:1-84:1), efficient and stereoselective routes to each of the four targeted inhibitors were achieved. The optimized synthetic route to the most potent inhibitor (syn,syn-4, Ki = 2.0 nM) proceeded in seven steps (87% average yield per step) from aminoindanol hydrocinnamide 40 and (S)-fluoroiodoacetic acid, and allowed for the preparation of more than 1 g of this compound. The inhibition of HIV-1 protease by each of the fluorinated inhibitors was evaluated in vitro, and the variation of potency as a function of inhibitor stereochemistry is discussed.

Synthetic studies for novel structure of α-nitrogenously functionalized α-fluorocarboxylic acids. Part III. Some reactions of α-bromo-α-fluorocarboxylic acids and their ethyl esters with sodium azide

Synthesis of a novel group of α-azido-α-fluorocarboxylic acid derivatives has been attempted by azidation of the corresponding α-bromo-α-fluorocarboxylic acids or ethyl esters.Although ethyl azidofluoroacetate was obtained, over-azidation occurred very readily in most cases to afford geminally diazidated compounds.Attemped conversion of ethyl azidofluoroacetate into azidofluoroacetic acid by alkaline hydrolysis or by treatment with trimethylsilyl bromide resulted mainly in the formation of defluorinated products.It was found that, although α-fluorocarboxylates are generally considered stable, defluorination occurs under nucleophilic conditions if an additional labilizing group is present on the same carbon atom as the fluorine.

RADICAL CYCLIZATION OF α-FLUORO-α-IODO AND α-IODO ESTERS AND AMIDES

The free radical cyclization of various unsaturated α-fluoro-α-iodo and α-iodo esters and amides is described.Unusual 12-membered dilactones and 18-membered trilactones were obtained under the standard atom transfer cyclization reaction conditions.