5839-93-0

Usage

Uses

Used in Pharmaceutical Industry:
4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE is used as a chiral building block for the synthesis of various pharmaceuticals. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for the development of drugs with specific therapeutic effects and minimal side effects.
Used in Agrochemical Industry:
In the agrochemical sector, 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE serves as a key intermediate in the synthesis of chiral pesticides and other agrochemicals. Its use ensures the production of enantiomerically pure active ingredients, enhancing the effectiveness and selectivity of these compounds in agricultural applications.
Used in Asymmetric Synthesis:
4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE is utilized as a versatile intermediate in asymmetric synthesis, a technique that allows for the selective production of one enantiomer of a chiral compound over another. This is particularly important in the synthesis of complex organic molecules, where the stereochemistry of the molecule can significantly impact its biological activity.
Used in Catalysis:
4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE's ability to form stable complexes with metal ions makes 4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE useful in catalytic processes. It can be employed as a ligand in homogeneous catalysis, facilitating various chemical reactions with improved efficiency and selectivity.
Used in Specialty Chemicals, Polymers, and Materials Production:
4-ISOPROPYL-2-PHENYL-2-OXAZOLINE-5-ONE finds applications in the production of specialty chemicals, polymers, and materials used across various industries. Its unique properties contribute to the development of innovative products with specific characteristics tailored to the needs of different sectors.

InChI:InChI=1/C12H13NO2/c1-8(2)10-12(14)15-11(13-10)9-6-4-3-5-7-9/h3-8,10H,1-2H3

Upstream product

• 2901-80-6 N-benzoyl-D,L-valine 
• 2901-80-6 N-benzoyl-L-valine 
• 2901-80-6 (2R)-2-(benzoylamino)-3-methylbutyric acid 
• 28897-81-6 2-phenyl-4-iso-propyl-4H-oxazolin-5-one 
• 107-18-6 allyl alcohol 
• 98-88-4 benzoyl chloride 
• 541-41-3 chloroformic acid ethyl ester 
• 65-85-0 benzoic acid 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 16975-39-6 2-(benzylamino)-3-methylbutanoic acid 
• 516-06-3 D,L-valine 
• 4491-47-8 2-phenyl-4-isopropylidene-5(4H)oxazolone 
• 108-24-7 acetic anhydride 

Downstream Products

• 1738-54-1 N-isobutyrylbenzamide 
• 182176-17-6 rac-4-(iodomethyl)-4-(2-methylpropyl)-2-phenyloxazol-5(4H)-one 
• 1492-13-3 N-benzoyl-L-valine methyl ester 
• 269393-48-8 N-[1-(3,4-dimethyl-benzoyl)-2-methyl-propyl]-benzamide 
• 269393-47-7 N-[2-methyl-1-(4-methyl-benzoyl)-propyl]-benzamide 
• 113535-07-2 N-(3-methyl-1-oxo-1-phenylbutan-2-yl)benzamide 
• 95885-55-5 4-isopropyl-2,4-diphenyl-4H-oxazol-5-one 
• 28897-81-6 (S)-4-isopropyl-2-phenyl-4H-oxazol-5-one 
• 5839-93-0 (R)-4-Isopropyl-2-phenyl-4H-oxazol-5-one 
• 110315-21-4 1-methoxy-6-nitro-3-phenyl-1H-indazole 
• 50709-78-9 6-nitro-3-phenyl-1H-indazol-1-ol 
• 110315-23-6 methyl N-benzoyl-2-(2,4-dinitrophenyl)valinate 
• 1207097-57-1 N-((S)-(2-fluorophenyl)((R)-4-isopropyl-5-oxo-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-4-methylbenzenesulfonamide 
• 1207097-52-6 N-((S)-((R)-4-isopropyl-5-oxo-2-phenyl-4,5-dihydrooxazol-4-yl)(phenyl)methyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Base-catalysed 18F-labelling of trifluoromethyl ketones. Application to the synthesis of 18F-labelled neutrophil elastase inhibitors

A new method for the fluorine-18 labelling of trifluoromethyl ketones has been developed. This method is based on the conversion of a-COCF3 functional group to a difluoro enol silyl ether followed by halogenation and fluorine-18 labelling. The utility of this new method was demonstrated by the synthesis of fluorine-18 labelled neutrophil elastase inhibitors, which are potentially useful for detection of inflammatory disorders.

Transformation of Racemic Azlactones into Enantioenriched Dihydropyrroles and Lactones Enabled by Hydrogen-Bond Organocatalysis

Azlactones, a potent building block for the synthesis of complex molecules, have been explored in an organocatalytic Mannich reaction with protected imines. In this study, azlactones containing a propargyl substituent were employed for the first time in organocatalysis so far. The catalytically active species responsible for high enantioselectivity with substrate containing such a small linear substituent is assembled in situ from a bifunctional thiourea, prone to dimerization, and an organic acid, as evidenced by DOSY NMR. The resulting α,β-diamino acid derivatives were subjected to further derivatization: as an example, gold-catalyzed intramolecular hydroamination of alkynes gave chiral spirocyclic dihydropyrrole. Alternatively, related squaramide catalyst enabled a Mannich reaction of azlactones with N-aryl or alkyl glyoxylate imines. Reduction of these adducts gave access to 2,3-diaminobutyrolactones or 2,3-diamino-1,4-diol with a tertiary and a quaternary stereocenter.

Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones

Insertion reactions of diazo carbonyls to azlactones in basic conditions have been performed. The developed method allows the preparation of a wide range of oxazole derivatives in yields ranging from 74 to 98%. Different substituents on both azlactone rings and diazo carbonyls do not compromise the methodology, even those containing stereogenic centers. Isotopic labeling experiments revealed the mechanism may proceed through a rare diazo carbonyl activation by an ammonium salt derivative.

Group-Assisted Purification Chemistry for Asymmetric Mannich-type Reaction of Chiral N-Phosphonyl Imines with Azlactones Leading to Syntheses of α-Quaternary α,β-Diamino Acid Derivatives ?

An asymmetric Mannich-type reaction between chiral N-phosphonyl imines and azlactones [oxazol-5(4H)-ones] has been established under convenient conditions at room temperature. The reaction was performed without using any bases, additives, or catalysts to achieve up to excellent chemical yields and diastereoselectivity for 32 examples. The α-quaternary syn-α,β-diamino acid products were purified simply by washing the crude mixtures with cosolvents, following the group-assisted purification chemistry/technology, without involving traditional chromatography or recrystallization methods. The auxiliary can be readily removed and recycled for reuse. The absolute configuration was unambiguously assigned by X-ray structural analysis.

One-Pot Vinylation of Azlactones: Fast Access to Enantioenriched α-Vinyl Quaternary Amino Acids

We report a fast one-pot protocol for the direct vinylation of azlactones [oxazol-5-(4H)-ones] by using as a key step an aldol addition with 2-(phenylselenenyl)acetaldehyde followed by dehydroxyselenation. The acid hydrolysis of the oxazolone ring gave the desired fully deprotected α-vinyl quaternary α-amino acids in almost quantitative yields. An enantioselective variant of the method was also developed by using catalytic chiral bases. The use of Sharpless ligand (DHQD)2PHAL produced the final quaternary amino acids in good overall yields (62–78 %) and with ee values up to 86 %. Scaling up the optimized protocol to gram quantities did not affect the yields and ee values. We also demonstrated that the vinyl moiety installed onto the oxazolone ring can be exploited as a handle for the attachment of aryl groups through a Heck coupling reaction.

BENZAMIDE TRPA1 ANTAGONISTS

Compounds of formula I, pharmaceutically acceptable salts thereof, diastereomers, enantiomers, or mixtures thereof: wherein R, X, Y, Z, n and A are as defined in the specification, as well as pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

Alkynyliodonium salt mediated alkynylation of azlactones: Fast access to Cα-tetrasubstituted α-amino acid derivatives

An efficient electrophilic alkynylation of azlactones (oxazol-5(4H)-ones) is developed using alkynyl(phenyl)iodonium salts as the electrophilic alkyne source. After remarkably short reaction times, the desired alkyne functionalized azlactones are obtained in 60-97% yield and can be transformed easily into a variety of quaternary α-amino acid derivatives.

Self-association free bifunctional thiourea organocatalysts: Synthesis of chiral α-amino acids via dynamic kinetic resolution of racemic azlactones

Concentration-independent high enantioselectivity in the dynamic kinetic resolution (DKR) of racemic azlactones affording chiral α-aminoesters has been achieved using self-association free thiourea-based dimeric cinchona alkaloid organocatalysts. Detailed