169737-77-3

Basic information

• Product Name: (2R,3S)-trans-epoxy-3-phenyl-1-(2-furyl)propan-1-one
• Synonyms: (2R,3S)-trans-epoxy-3-phenyl-1-(2-furyl)propan-1-one
• CAS NO: 169737-77-3
• Molecular Weight: 214.221
• Mol File: 169737-77-3.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S)-trans-epoxy-3-phenyl-1-(2-furyl)propan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-trans-epoxy-3-phenyl-1-(2-furyl)propan-1-one(169737-77-3)
• EPA Substance Registry System: (2R,3S)-trans-epoxy-3-phenyl-1-(2-furyl)propan-1-one(169737-77-3)

Safety Data

• Hazardous Substances Data: 169737-77-3(Hazardous Substances Data)

Upstream product

• 3988-74-7 1-(2-furyl)-3-phenylpropen-1-one 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 98-01-1 furfural 
• 1312775-51-1 3-(tert-butylperoxy)-1-(furan-2-yl)-3-phenylpropan-1-one 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 55984-17-3 2-chloroacetylfuran 
• 3988-74-7 (E)-1-(furan-2-yl)-3-phenylprop-2-en-1-one 

Relevant articles and documents

Stabilized α-helix-catalyzed enantioselective epoxidation of α,β-unsaturated ketones

(Equation Presented). Chiral cyclic α-amino acid containing oligopeptide catalyzed highly enantioselective epoxidation of α,β-unsaturated ketones and the α-helical secondary structure of the peptide catalyst were revealed by X-ray crystallographic analysis.

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe3)2]3with chiral TADDOL ligands

The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that

Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst

Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).

Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts

A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.

Organocatalytic Enantioselective γ-Elimination: Applications in the Preparation of Chiral Peroxides and Epoxides

An organocatalyzed enantioselective γ-elimination process has been achieved and applied in the kinetic resolution of peroxides to access chiral peroxides and epoxides. The reaction provided a pathway for the preparation of two useful synthetic and biologically important structural motifs through a single-step reaction. A range of substrates has been resolved with a selectivity factor up to 63. The obtained enantioenriched peroxides and epoxides allowed a series of transformations with retained optical purities.

Lanthanide complexes combined with chiral salen ligands: Application in the enantioselective epoxidation reaction of α,β-unsaturated ketones

Readily available lanthanide amides Ln[N(SiMe3)2]3 (Ln = Nd (1), Sm (2), Eu (3), Yb (4), La (5)), combined with chiral salen ligands H2La ((S,S)-N,N′-di-(3,5-disubstituted-salicylidene)-1,2-cyclohexan

Chiral calcium-catalyzed asymmetric epoxidation reactions using hydrogen peroxide as the terminal oxidant

Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivitie

Asymmetric epoxidation of unsaturated ketones catalyzed by heterobimetallic rare earth-lithium complexes bearing phenoxy-functionalized chiral diphenylprolinolate ligand

Four novel heterobimetallic complexes [REL2]{[(THF)3Li]2(μ-Cl)} stabilized by chiral phenoxy-functionalized prolinolate (RE = Yb (1), Y (2), Sm (3), Nd (4), H2L = (S)-2,4-di-tert-butyl-6-[[2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]methyl]phenol have been synthesized and characterized. These readily available complexes are highly active in catalyzing the epoxidation of α,β-unsaturated ketones, while the enantioselectivity varies according to the ionic radii of the rare earth center. A series of chalcone derivatives were converted to chiral epoxides in 80 → 99% ee at 0 °C using TBHP as the oxidant in the presence of 10 mol % of 1.

Enantioselective synthesis of heteroaromatic epoxyketones under phase-transfer catalysis using D-glucose- and D-mannose-based crown ethers

Heteroaromatic epoxyketones have been synthesized in an asymmetric Darzens condensation of 2-chloroacetylfuran or 2- and 3-chloroacetylthiophene with aromatic aldehydes and in the enantioselective epoxidation of α,β-enones with an N-methylpyrrole unit, in

Asymmetric C-C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers

Liquid-liquid phase asymmetric Darzens condensations were promoted by d-glucose- and d-mannose-based crown ethers. The corresponding aromatic and heteroaromatic α,β-epoxyketones were obtained with moderate to high enantioselectivities (up to 96%) as well