3449-63-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Fluorophenyl)glutaric acid is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its unique structure allows for the creation of molecules with specific therapeutic properties, enhancing the range of treatments available for various medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(4-Fluorophenyl)glutaric acid is utilized as an intermediate in the production of agrochemicals, contributing to the development of effective compounds for crop protection and enhancement of agricultural yields.
Used in Organic Compounds Production:
3-(4-Fluorophenyl)glutaric acid is used as a building block for the production of various organic compounds, playing a crucial role in the synthesis of complex organic molecules for a wide range of applications, including but not limited to materials science, chemical research, and specialty chemicals manufacturing.
Used in Medicinal Chemistry Research:
3-(4-Fluorophenyl)glutaric acid is employed as a subject of research in medicinal chemistry, where its potential therapeutic properties are being explored. This involves investigating its interactions with biological targets and assessing its efficacy in treating specific diseases or conditions.

InChI:InChI=1/C11H11FO4/c12-9-3-1-7(2-4-9)8(5-10(13)14)6-11(15)16/h1-4,8H,5-6H2,(H,13,14)(H,15,16)

Upstream product

• 3449-43-2 2,6-Dihydroxy-2,6-bis-trifluormethyl-4-<4-fluor-phenyl>-tetrahydropyran-dicarbonsaeure-(3,5)-diethylester 
• 141-97-9 ethyl acetoacetate 
• 459-57-4 4-fluorobenzaldehyde 
• 105-53-3 diethyl malonate 
• 50737-52-5 ethyl 2-cyano-3-(4-fluorophenyl)acrylate 
• 1407597-82-3 tetramethyl-2-(4-fluorophenyl)propane-1,1,3,3-tetracarboxylate 
• 52927-40-9 dimethyl 2-(4-fluorobenzylidene)malonate 
• 125080-12-8 ethyl 4-fluorobenzalacetoacetate 
• 349446-90-8 2-(4-fluorophenyl)-1,1,3-trimethoxy carbonyl propane 
• 100891-10-9 methyl p-fluorocinnamate 
• 459-32-5 4-fluorocinnamic acid 
• 216690-15-2 dimethyl 3-(4-fluorophenyl)glutarate 
• 223513-93-7 diethyl 3-(4-fluorophenyl)pentanedioate 
• 420808-42-0 dimethyl 2-(4-fluorophenyl)-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylate 

Downstream Products

• 865367-11-9 (S)-3-(4-fluorophenyl)-glutaric acid monoethyl ester 
• 865367-14-2 (S)-3-(4-fluorophenyl)-glutaric acid monoallyl ester 
• 865367-12-0 (S)-3-(4-fluorophenyl)-glutaric acid monobutyl ester 
• 865367-13-1 (S)-3-(4-fluorophenyl)-glutaric acid monobenzyl ester 
• 4759-75-5 3-(4-fluorophenyl)-glutaric acid monomethyl ester 
• 216690-16-3 (3R)-methyl hydrogen 3-(4-fluorophenyl)pentane-1,5-dioate 
• 511283-89-9 4-(4-fluorophenyl)-1-methylpiperidine-2,6-dione 
• 223513-93-7 diethyl 3-(4-fluorophenyl)pentanedioate 
• 1263798-90-8 5-(acetyloxy)-3-(4-fluorophenyl)pentanoic acid 
• 1263799-17-2 methyl 3-(4-fluorophenyl)-5-hydroxypentanoate 

Relevant academic research and scientific papers

A phosphine-free iron complex-catalyzed synthesis of cycloalkanes: Via the borrowing hydrogen strategy

Herein we report a diaminocyclopentadienone iron tricarbonyl complex catalyzed synthesis of substituted cyclopentane, cyclohexane and cycloheptane compounds using the borrowing hydrogen strategy in the presence of various substituted primary and secondary 1,n diols as alkylating reagents. Deuterium labeling experiments confirm that the diols were the hydride source in this cascade process. This journal is

Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach

A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled.

Stereoselective Synthesis of Cyclohexanes via an Iridium Catalyzed (5 + 1) Annulation Strategy

An iridium catalyzed method for the synthesis of functionalized cyclohexanes from methyl ketones and 1,5-diols is described. This process operates by two sequential hydrogen borrowing reactions, providing direct access to multisubstituted cyclic products with high levels of stereocontrol. This methodology represents a novel (5 + 1) strategy for the stereoselective construction of the cyclohexane core.

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X7 receptor antagonists

A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists.

Cloning, expression and characterization of a new enantioselective esterase from a marine bacterium Pelagibacterium halotolerans B2T

An esterase, designated as PE8 (219 aa, 23.19 kDa), was cloned from a marine bacterium Pelagibacterium halotolerans B2T and overexpressed in Escherichia coli Rosetta, resulting an active, soluble protein which constituted 23.1% of the total cell protein content. Phylogenetic analysis of the protein showed it was a new member of family VI lipolytic enzymes. Biochemical characterization analysis showed that PE8 preferred short chain p-nitrophenyl esters (C2-C6), exhibited maximum activity toward p-nitrophenyl acetate, and was not a metalloenzyme. PE8 was an alkaline esterase with an optimal pH of 9.5 and an optimal temperature of 45 C toward p-nitrophenyl acetate. Furthermore, it was found that PE8 exhibited activity and enantioselectivity in the synthesis of methyl (R)-3-(4-fluorophenyl)glutarate ((R)-3-MFG) from the prochiral dimethyl 3-(4-fluorophenyl)glutarate (3-DFG). (R)-3-MFG was obtained in 71.6% ee and 73.2% yield after 36 h reaction under optimized conditions (0.6 M phosphate buffer (pH 8.0) containing 17.5% 1,4-dioxane under 30 C). In addition, PE8 was tolerant to extremely strong basic and high ionic strength solutions as it exhibited high activity even at pH 11.0 in 1 M phosphate buffer. Given its highly soluble expression, alkalitolerance, halotolerance and enantioselectivity, PE8 could be a promising candidate for the production of (R)-3-MFG in industry. The results also demonstrate the potential of the marine environment as a source of useful biocatalysts.

An enantiodivergent and formal synthesis of paroxetine enantiomers by asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride with a chiral SuperQuat oxazolidin-2-one

The asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride 9 with lithiated chiral oxazolidin-2-one 8 has been studied. The desymmetrized product was formed with >90% de and converted into known intermediates for both (+)- and (-)-paroxetines.

ALLOSTERIC PROTEIN KINASE MODULATORS

The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

Complementary lipase-mediated desymmetrization processes of 3-Aryl-1,5-disubstituted fragments. enantiopure synthetic valuable carboxylic acid derivatives

Desymmetrizaton enzymatic processes have been extensively studied searching for optimal methods of producing enantioenriched monoacetates from prochiral diols and diesters. AK lipase has been found as an excellent biocatalyst for the desymmetriaztion of a series of previously synthesized 3-arylpentane-1,5-diols derivatives. The access to (S)- or (R)-monoacetates in high optical purity (86-99% ee) has been possible by using acetylation or hydrolysis reactions, respectively, where the reaction parameters have been optimized in terms of source and amount of biocatalyst, temperature, solvent, and reaction time. The synthetic potential of enantiopure monoesters has been demonstrated by using these interesting chiral building blocks for the preparation of novel enantiopure carboxylic acid derivatives.

The first asymmetric synthesis of a 4-aryl-substituted 5-carboxy-3,4-dihydropyridin-2-one derivative

A simple and practical route for the asymmetric synthesis of (S)-4-(4-fluorophenyl)-1,4,5,6-tetrahydro-6-oxo-3-pyridinecarboxylic acid (1) is presented. The procedure comprises catalytic desymmetrization of a meso-anhydride using a chiral thiourea organocatalyst, followed by selective formylation and cyclization.