40327-67-1

Basic information

• Product Name: (-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one
• CAS NO: 40327-67-1
• Molecular Weight: 230.287
• Mol File: 40327-67-1.mol

Chemical Properties

• CAS DataBase Reference: (-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one(40327-67-1)
• EPA Substance Registry System: (-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one(40327-67-1)

Safety Data

• Hazardous Substances Data: 40327-67-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one is utilized as a key intermediate for the synthesis of pharmaceuticals due to its unique structure and reactivity, which allows for the creation of biologically active compounds with potential therapeutic applications.
Used in Natural Product Synthesis:
(-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one is also employed as an important building block in the synthesis of natural products, leveraging its stereochemistry to produce complex molecules with potential biological activity.
Used in Organic Synthesis Research:
(-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one is used as a valuable target in organic synthesis research to explore new methods and reactions that can lead to the development of innovative synthetic pathways and compounds.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (-)-2(R),3(S)-epoxy-3-phenyl-1-(2-thienyl)propan-1-one is applied to study its interactions with biological targets and to understand its potential as a precursor for the development of new drugs and therapeutic agents.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 100-42-5 styrene 
• 1312775-52-2 3-(tert-butylperoxy)-3-phenyl-1-(thiophen-2-yl)propan-1-one 
• 3988-77-0 2-cinnamoylthiophene 
• 3988-77-0 3-phenyl-1-thiophen-2-yl-propenone 
• 29683-77-0 2-chloro-1-(thiophen-2-yl)ethanone 
• 100-52-7 benzaldehyde 
• 88-15-3 2-Acetylthiophene 
• 14531-55-6 3,5-dimethyl-4-nitro-1H-pyrazole 

Downstream Products

• 135460-31-0 2-Hydroxy-3-brom-1--3-phenyl-propan-1-on 

Relevant articles and documents

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.).

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

Asymmetric synthesis of new γ-butenolides: Via organocatalyzed epoxidation of chalcones

γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.

Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric ring-opening with pyrazole derivatives

A highly efficient catalytic kinetic resolution of 2,3-epoxy 3-aryl ketones via asymmetric ring-opening with pyrazole derivatives has been achieved by using a chiral N,N′-dioxide-Sc(III) complex as the catalyst. A wide variety of substrates were readily scoped, and the selectivity factors obtained were excellent (up to >300).

Synthesis of L-arabinose-based crown ethers and their application as enantioselective phase transfer catalysts

New chiral monoaza-15-crown-5 type macrocycles anellated to 3,4-O-isopropylidene-β-L-arabinopyranose (5a-b), to β-L- arabinopyranose (6) and to 3,4-O-benzyliden-β-L-arabinopyranose (11) have been synthesized. The cation binding ability of the new lariat e

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

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Iron-catalyzed carbonylation-peroxidation of alkenes with aldehydes and hydroperoxides

A three-component reaction of alkenes, aldehydes, and hydroperoxides catalyzed by FeCl2 to β-peroxy ketones has been achieved. This three-component reaction can be also applied to the synthesis of α-carbonyl epoxides, through either a stepwise base-induced epoxidation of the separated β-peroxy ketone products or a one-pot process by simply adding base to the reaction mixture after the completion of the three-component reaction.

Synthesis of (αR,βS)-epoxyketones by asymmetric epoxidation of chalcones with cinchona phase-transfer catalysts

An efficient method to synthetically produce optically enriched (αR,βS)-epoxyketones was developed using a quaternary ammonium salt derived from cinchona alkaloid as the chiral phase-transfer catalyst. (αR,βS)-Epoxyketones were prepared in high optical purities (91-99% ee) by the asymmetric epoxidation of 1,3-diarylenones with aqueous sodium hypochlorite in the presence of a hydrocinchonine-derived chiral phase-transfer catalyst bearing a 2,3,4-trifluorobenzyl group.