1254701-84-2

Basic information

• Product Name: (5R,6S)-5-bromo-6-phenyltetrahydro-2H-pyran-2-one
• Synonyms: (5R,6S)-5-bromo-6-phenyltetrahydro-2H-pyran-2-one
• CAS NO: 1254701-84-2
• Molecular Weight: 255.111
• Mol File: 1254701-84-2.mol

Chemical Properties

• CAS DataBase Reference: (5R,6S)-5-bromo-6-phenyltetrahydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6S)-5-bromo-6-phenyltetrahydro-2H-pyran-2-one(1254701-84-2)
• EPA Substance Registry System: (5R,6S)-5-bromo-6-phenyltetrahydro-2H-pyran-2-one(1254701-84-2)

Safety Data

• Hazardous Substances Data: 1254701-84-2(Hazardous Substances Data)

Upstream product

• 28525-69-1 (4E)-5-phenyl-4-pentenoic acid 
• 17920-83-1 5-phenyl-4-pentenoic acid 

Downstream Products

• 1379786-29-4 (1S,4R,5R)-4-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 1379786-28-3 (5S,6S)-5-azido-6-phenyltetrahydro-2H-pyran-2-one 

Relevant articles and documents

Studies toward Lewis basic thiocarbamate and thiourea mediated bromolactonization: The effect of a trace amount of water on the reactivity and enantioselectivity

The effects of trace amounts of water on thiocarbamate- and thiourea-catalyzed bromolactonization reactions are studied. It was found that the thiourea- and the N-Me thiocarbamate-catalyzed bromolactonization reactions were sensitive to trace amounts of m

A Catalyst-Controlled Enantiodivergent Bromolactonization

A catalyst-controlled enantiodivergent bromolactonization of olefinic acids has been developed. Quinine-derived amino-amides bearing the same chiral core but different achiral aryl substituents were used as the catalysts. Switching the methoxy substituent in the aryl amide system from meta- to ortho-position results in a complete switch in asymmetric induction to afford the desired lactone in good enantioselectivity and yield. Mechanistic studies, including chemical experiments and density functional theory calculations, reveal that the differences in steric and electronic effects of the catalyst substituent alter the reaction mechanism.

Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications

A general protocol is described for inducing enantioselective halolactonizations of unsaturated carboxylic acids using novel bifunctional organic catalysts derived from a chiral binaphthalene scaffold. Bromo- and iodolactonization reactions of diversely substituted, unsaturated carboxylic acids proceed with high degrees of enantioselectivity, regioselectivity, and diastereoselectivity. Notably, these BINOL-derived catalysts are the first to induce the bromo- and iodolactonizations of 5-alkyl-4(Z)-olefinic acids via 5-exo mode cyclizations to give lactones in which new carbon-halogen bonds are created at a stereogenic center with high diastereo- and enantioselectivities. Iodolactonizations of 6-substituted-5(Z)-olefinic acids also occur via 6-exo cyclizations to provide δ-lactones with excellent enantioselectivities. Several notable applications of this halolactonization methodology were developed for desymmetrization, kinetic resolution, and epoxidation of Z-alkenes. The utility of these reactions is demonstrated by their application to a synthesis of precursors of the F-ring subunit of kibdelone C and to the shortest catalytic, enantioselective synthesis of (+)-disparlure reported to date.

Catalytic asymmetric bromolactonization reactions using (DHQD) 2PHAL-benzoic acid combinations

Catalytic (DHQD)2PHAL as modified by added benzoic acid, is an off-the-shelf catalyst-additive combination for effecting catalytic asymmetric bromolactonization reactions. This combination delivers bromolactones with asymmetric induction at a c

Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst

A facile, highly regio- and enantioselective amino-thiocarbamate-catalyzed bromolactonization of cis-1,2-disubstituted olefinic acids has been developed. The use of the enantio-enriched lactones in the synthesis of chiral synthetic intermediates is also demonstrated. 2012

Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds

A novel bifunctional catalyst derived from BINOL has been developed that promotes the highly enantioselective bromolactonizations of a number of structurally distinct unsaturated acids. Like some known catalysts, this catalyst promotes highly enantioselec

Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids

An efficient and enantioselective bromolactonization of 1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst has been developed, resulting in the formation of δ-lactones containing two chiral centers with up to 99% yield, 95% ee.