90432-58-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyrrolidinone, 5-(4-fluorophenyl)is used as a drug intermediate for its potential in the synthesis of pharmaceuticals. Its unique molecular structure allows for versatile chemical reactions, contributing to the development of new medications.
Used in Agrochemical Industry:
In the agrochemical field, 2-Pyrrolidinone, 5-(4-fluorophenyl)may be utilized in the development of new compounds for agricultural applications, such as pesticides or herbicides, due to its chemical properties and reactivity.
Used in Research:
2-Pyrrolidinone, 5-(4-fluorophenyl)serves as a valuable compound in research settings, where its properties and potential uses are further explored. It may contribute to the advancement of organic chemistry and the discovery of new materials or reactions.
Used in Organic Chemistry:
As a building block in organic chemistry reactions, 2-Pyrrolidinone, 5-(4-fluorophenyl)facilitates the synthesis of various organic compounds, expanding the scope of chemical research and development.
Overall, 2-Pyrrolidinone, 5-(4-fluorophenyl)holds promise for a range of applications across different industries, and further research into its properties and potential uses is warranted.

Upstream product

• 77287-34-4 formamide 
• 366-77-8 4-(4-fluorophenyl)-4-oxopropionic acid 
• 39769-08-9 N-(4-fluorobenzylidene)-4-methoxyaniline 
• 175212-06-3 tert-butyl 4-(4-fluorophenyl)-4-oxobutanoate 
• 352-13-6 4-flourophenylmagnesium bromide 
• 39560-31-1 methyl 3-(4-fluorobenzoyl)-propionate 
• 90432-64-7 N-<(R)-1-(1-naphthyl)ethyl>-5-(4-fluorophenyl)-2-pyrrolidone-1-carboxamide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 589-06-0 4-(4-fluorophenyl)butanoic acid 
• 5724-03-8 1-(4-fluorophenyl)allyl alcohol 
• 688362-62-1 (S)-1-(4-fluorophenyl)-2-propenylamine 
• 1431851-21-6 (S)-N-(1-(4-fluorophenyl)allyl)formamide 
• 90432-64-7 N-<(R)-1-(1-naphthyl)ethyl>-5-(4-fluorophenyl)-2-pyrrolidone-1-carboxamide 
• 133188-66-6 4-(4-fluorophenyl)butyryl chloride 

Downstream Products

• 90432-64-7 N-<(R)-1-(1-naphthyl)ethyl>-5-(4-fluorophenyl)-2-pyrrolidone-1-carboxamide 
• 90432-64-7 N-<(R)-1-(1-naphthyl)ethyl>-5-(4-fluorophenyl)-2-pyrrolidone-1-carboxamide 
• 1437789-65-5 C₂₆H₂₀FN₃O₂ 
• 264122-81-8 1-(tert-butyloxycarbonyl)-5-(4-fluorophenyl)-pyrrolidin-2-one 

Relevant academic research and scientific papers

Method for synthesizing chiral lactam through tandem reductive amination

The invention belongs to the technical field of chemical synthesis preparation, and particularly relates to a method for synthesizing chiral lactam through tandem reductive amination, which successfully realizes ruthenium-catalyzed asymmetric reductive amination/cyclization tandem reaction to efficiently construct chiral lactam by using substrates of keto acid and keto ester.

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.

A class of histone acetylase p300 inhibitors, and application thereof

The invention discloses a class of histone acetylase p300 inhibitors, and application thereof, and belongs to the technical field of medicinal chemistry. The invention discloses a compound representedby a formula (I), or a stereochemical isomer, a solvate or a pharmaceutically acceptable salt thereof. According to the invention, the compound can effectively inhibit the activity of histone acetylase p300 and can effectively inhibit the proliferation activity of various tumor cells; the compound is combined with a CDK4/6 inhibitor to play a synergistic role in inhibiting proliferation of tumorcells; and the compound has good application prospects in preparation of histone acetylase inhibitors, preparation of drugs for preventing and/or treating cancers, metabolic diseases, neurological diseases or inflammations, and combination of drugs.

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

COMPOUND HAVING BET INHIBITORY ACTIVITY AND PREPARATION METHOD AND USE THEREFOR

The invention relates to the field of pharmaceutical chemistry. Specifically, the present invention relates to a series of BET (bromodomain and extra-terminal domain) inhibitors having a novel structure, particularly inhibitors targeting BRD4 (Bromodomain-containing protein 4), and a preparation method and use therefor. The structure thereof is shown in the following general formula (I). Said compounds or a stereoisomer, racemate, geometric isomer, tautomer, prodrug, hydrate, solvate, or crystal form thereof, or a pharmaceutically acceptable salt thereof, and the pharmaceutical compsosition thereof can be used for the treatment and/or prevention of related diseases mediated by bromodomain proteins.

A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen

Lactams are privileged in bioactive natural products and pharmaceutical agents and widely featured in functional materials. This study presents a novel versatile approach to the direct synthesis of lactams from oxocarboxylic acids without catalyst or external hydrogen. The method involves the in situ release of formic acid from formamides induced by water to facilitate efficient cycloamination. Water also suppresses the formation of byproducts. This unconventional pathway is elucidated by a combination of model experiments and density functional theory calculations, whereby cyclic imines (5-methyl-3,4-dihydro-2-pyrrolone and its tautomeric structures) are found to be favorable intermediates toward lactam formation, in contrast to the conventional approach encompassing cascade reductive amination and cyclization. This sustainable and simple protocol is broadly applicable for the efficient production of various N-unsubstituted and N-substituted lactams.

RETRACTED ARTICLE: Site-selective enzymatic C-H amidation for synthesis of diverse lactams

A major challenge in carbon?hydrogen (C?H) bond functionalization is to have the catalyst control precisely where a reaction takes place. In this study, we report engineered cytochrome P450 enzymes that perform unprecedented enantioselective C?H amidation reactions and control the site selectivity to divergently construct b-, g-, and d-lactams, completely overruling the inherent reactivities of the C?H bonds. The enzymes, expressed in Escherichia coli cells, accomplish this abiological carbon?nitrogen bond formation via reactive iron-bound carbonyl nitrenes generated from nature-inspired acyl-protected hydroxamate precursors. This transformation is exceptionally efficient (up to 1,020,000 total turnovers) and selective (up to 25:1 regioselectivity and 97%, please refer to compound 2v enantiomeric excess), and can be performed easily on preparative scale.

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation

A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

Synthetic Utility of N-Benzoyloxyamides as an Alternative Precursor of Acylnitrenoids for γ-Lactam Formation

Described herein is the development of a new entry of acylnitrenoid precursors for γ-lactam synthesis via an intramolecular C-H amidation reaction. Upon Ir catalysis, N-benzoyloxyamides serve as efficient substrates to afford 5-membered amides. Mechanistic studies revealed that the generation of a putative Ir-carbonylnitrenoid via N-O bond cleavage is facilitated by the chelation of countercations. This protocol offers a convenient and step-economic route to γ-lactams starting from the corresponding carboxylic acids.

Harnessing Secondary Coordination Sphere Interactions That Enable the Selective Amidation of Benzylic C-H Bonds

Engineering site-selectivity is highly desirable especially in C-H functionalization reactions. We report a new catalyst platform that is highly selective for the amidation of benzylic C-H bonds controlled by π-πinteractions in the secondary coordination sphere. Mechanistic understanding of the previously developed iridium catalysts that showed poor regioselectivity gave rise to the recognition that the π-cloud of an aromatic fragment on the substrate can act as a formal directing group through an attractive noncovalent interaction with the bidentate ligand of the catalyst. On the basis of this mechanism-driven strategy, we developed a cationic (ν5-C5H5)Ru(II) catalyst with a neutral polypyridyl ligand to obtain record-setting benzylic selectivity in an intramolecular C-H lactamization in the presence of tertiary C-H bonds at the same distance. Experimental and computational techniques were integrated to identify the origin of this unprecedented benzylic selectivity, and robust linear free energy relationship between solvent polarity index and the measured site-selectivity was found to clearly corroborate that the solvophobic effect drives the selectivity. Generality of the reaction scope and applicability toward versatile γ-lactam synthesis were demonstrated.