7116-38-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Fluoro-phenyl)-propionic acid ethyl ester is used as a non-steroidal anti-inflammatory drug (NSAID) for its analgesic, anti-inflammatory, and anti-pyretic properties. It is particularly effective in providing relief from mild to moderate pain and inflammation associated with various conditions such as arthritis, menstrual cramps, and muscular injuries.
Used in Medical Applications:
In the medical field, 3-(4-Fluoro-phenyl)-propionic acid ethyl ester is utilized for its therapeutic benefits in managing pain and reducing inflammation. Its use is recommended under the guidance of healthcare professionals to ensure safe and effective treatment while minimizing potential side effects and interactions with other medications.

InChI:InChI=1/C11H13FO2/c1-2-14-11(13)8-5-9-3-6-10(12)7-4-9/h3-4,6-7H,2,5,8H2,1H3

Upstream product

• 3054-95-3 acrylaldehyde diethyl acetal 
• 352-34-1 4-fluoro-1-iodobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 459-56-3 4-fluorobenzylic alcohol 
• 1071-46-1 hydrogen ethyl malonate 
• 405-99-2 para-fluorostyrene 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 459-31-4 3-(4-fluorophenyl)propanoic acid 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 59223-74-4 1,3-diethyl 2-[(4-fluorophenyl)methyl]propanedioate 
• 459-46-1 4-Fluorobenzyl bromide 
• 459-32-5 4-fluorocinnamic acid 

Downstream Products

• 116608-92-5 5-(4-Fluoro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 63416-70-6 3-(4-fluorophenyl)propanal 
• 702-15-8 3-(4-fluorophenyl)propan-1-ol 
• 24484-55-7 1-bromo-3-(4-fluorophenyl)propane 
• 917247-89-3 rac-2-hydroxy-4-(4-fluorophenyl)butanoic acid 
• 114990-93-1 (R)-2-hydroxy-4-(4-fluorophenyl)butanoic acid 
• 225233-79-4 rac-2-amino-4-(4-fluorophenyl)butanoic acid 
• 168166-37-8 3-(4-fluorophenylmethyl)-5-nitro-1H-indole 
• 168166-72-1 3-[5-Amino-3-(4-fluoro-benzyl)-indol-1-yl]-propionic acid methyl ester 
• 168166-54-9 methyl 3-(4-fluorophenylmethyl)-5-nitro-1H-indole-1-propanoate 
• 168167-35-9 3-[5-Benzenesulfonylamino-3-(4-fluoro-benzyl)-indol-1-yl]-propionic acid methyl ester 
• 168167-03-1 3-[3-(4-Fluoro-benzyl)-5-(toluene-4-sulfonylamino)-indol-1-yl]-propionic acid methyl ester 
• 168166-82-3 methyl 5-((4-fluorophenylsulphonyl)amino)-3-(4-fluorophenylmethyl)-1H-indole-1-propanoate 
• 168166-83-4 methyl 5-((4-chlorophenylsulphonyl)amino)-3-(4-fluorophenylmethyl)-1H-indole-1-propanoate 

Relevant academic research and scientific papers

Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand

The invention discloses a method for preparing organic carboxylic ester by combined catalysis of an aryl bidentate phosphine ligand. The method comprises the following steps: under the action of a palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, carrying out a hydrogen esterification reaction on terminal olefin, carbon monoxide and alcohol so as to generate theorganic carboxylic ester with one more carbon than olefin. According to the invention, by adoption of the palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, good catalytic activity and selectivity for the hydrogen esterification reaction of the olefin are achieved, and olefin carbonylation to synthesize organic carboxylic ester can be efficiently catalyzed. Thearyl bidentate phosphine ligand has a rigid skeleton structure of a rigid ligand and the flexibility of a flexible ligand, so the aryl bidentate phosphine ligand has proper flexibility due to the characteristic that the aryl bidentate phosphine ligand is soft and rigid, and a most favorable coordination mode and a stable active structure in space are favorably formed. In addition, the aryl bidentate phosphine ligand has the advantages of high stability, simple and convenient synthesis method and the like; and a novel industrial technology is provided for production of organic carboxylate compounds.

Radical dehydroxylative alkylation of tertiary alcohols by Ti catalysis

Deoxygenative radical C?C bond-forming reactions of alcohols are a long-standing challenge in synthetic chemistry, and the current methods rely on multistep procedures. Herein, we report a direct dehydroxylative radical alkylation reaction of tertiary alcohols. This new protocol shows the feasibility of generating tertiary carbon radicals from alcohols and offers an approach for the facile and precise construction of all-carbon quaternary centers. The reaction proceeds with a broad substrate scope of alcohols and activated alkenes. It can tolerate a wide range of electrophilic coupling partners, including allylic carboxylates, aryl and vinyl electrophiles, and primary alkyl chlorides/bromides, making the method complementary to the cross-coupling procedures. The method is highly selective for the alkylation of tertiary alcohols, leaving secondary/primary alcohols (benzyl alcohols included) and phenols intact. The synthetic utility of the method is highlighted by its 10-g-scale reaction and the late-stage modification of complex molecules. A combination of experiments and density functional theory calculations establishes a plausible mechanism implicating a tertiary carbon radical generated via Ti-catalyzed homolysis of the C?OH bond.

Anodic benzylic C(sp3)-H amination: Unified access to pyrrolidines and piperidines

An electrochemical aliphatic C-H amination strategy was developed to access the important heterocyclic motifs of pyrrolidines and piperidines within a uniform reaction protocol. The mechanism of this unprecedented C-H amination strategy involves anodic C-H activation to generate a benzylic cation, which is efficiently trapped by a nitrogen nucleophile. The applicability of the process is demonstrated for 40 examples comprising both 5- and 6-membered ring formations.

4-alkyloxyimino derivatives of uridine-5′-triphosphate: Distal modification of potent agonists as a strategy for molecular probes of P2Y 2, P2Y4, and P2Y6 receptors

Extended N4-(3-arylpropyl)oxy derivatives of uridine-5′-triphosphate were synthesized and potently stimulated phospholipase C stimulation in astrocytoma cells expressing G protein-coupled human (h) P2Y receptors (P2YRs) activated by UTP (P2Y2/4R) or UDP (P2Y6R). The potent P2Y4R-selective N4-(3- phenylpropyl)oxy agonist was phenyl ring-substituted or replaced with terminal heterocyclic or naphthyl rings with retention of P2YR potency. This broad tolerance for steric bulk in a distal region was not observed for dinucleoside tetraphosphate agonists with both nucleobases substituted. The potent N 4-(3-(4-methoxyphenyl)-propyl)oxy analogue 19 (EC50: P2Y2R, 47 nM; P2Y4R, 23 nM) was functionalized for chain extension using click tethering of fluorophores as prosthetic groups. The BODIPY 630/650 conjugate 28 (MRS4162) exhibited EC50 values of 70, 66, and 23 nM at the hP2Y2/4/6Rs, respectively, and specifically labeled cells expressing the P2Y6R. Thus, an extended N4-(3- arylpropyl)oxy group accessed a structurally permissive region on three G q-coupled P2YRs, and potency and selectivity were modulated by distal structural changes. This freedom of substitution was utilized to design of a pan-agonist fluorescent probe of a subset of uracil nucleotide-activated hP2YRs.

Assembly and post-modification of a metal-organic nanotube for highly efficient catalysis

A metal-organic nanotube (MONT) was synthesized by linking up the bent organic ligands and the tetra-coordinated zinc cations under mild conditions. Structural analysis revealed that the MONT has a very large exterior wall diameter of 4.91 nm and an interior channel diameter of 3.32 nm. Interlocking of the nanotubes gives rise to a 3D chiral framework containing 1D helical cylindered channels with diameter of 2.0 nm. The MONT has very interesting property by synergizing the functionality of nanotubes, metal-organic frameworks (MOFs), and N-heterocyclic carbenes (NHCs). The dye adsorption experiments demonstrate that the channels of the MONTs are accessible to large reagents typically used for catalysis. The postmodification of the MONT can be easily operated by unmarking the imidazolium moieties in the channel walls, which was conducted as a highly active heterogeneous catalyst for Suzuki-Miyaura and Heck coupling reactions, hydrogenation of olefins and nitrobenzene, while the constituent elements are less efficient for these reactions under the same conditions.

C-C bond formation from alcohols and malonate half esters using borrowing hydrogen methodology

Alcohols have been used as alkylating agents in a decarboxylative reaction with malonate half esters via a borrowing hydrogen pathway catalysed by readily available Ru(PPh3)3Cl2.

Biocatalytic racemization of (hetero)aryl-aliphatic α- hydroxycarboxylic acids by Lactobacillus spp. proceeds via an oxidation-reduction sequence

The biocatalytic racemization of a range of (hetero)aryl- and (di)aryl-aliphatic α-hydroxycarboxylic acids has been achieved by using whole resting cells of Lactobacillus spp. The essentially mild (physiological) reaction conditions ensure the suppression of undesired side reactions, such as elimination, decomposition or condensation. Cofactor/inhibitor studies using a cell-free extract of Lactobacillus paracasei DSM 20207 reveal that the addition of redox cofactors (NAD+/NADH) leads to a distinct increase in the racemization rate, while strong inhibition is observed in the presence of Thio-NAD+, which suggests that the racemization proceeds by an oxidation-reduction sequence rather than involvement of a "racemase" enzyme. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a range of 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)

We report the preliminary results of the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a number of phenyl alkyl imidazole-based compounds as inhibitors of the two components of 17α-hydroxylase/17,20-lyase (P45017α), that is, 17α-hydroxylase (17α-OHase) and 17,20-lyase (lyase). The results show that N-3-(4-bromophenyl) propyl imidazole (12) (IC50 = 2.95 μM against 17α-OHase and IC50 = 0.33 μM against lyase) is the most potent compound within the current study, in comparison to ketoconazole (KTZ) (IC50 = 3.76 μM against 17α-OHase and IC50 = 1.66 μM against lyase). Modelling of these compounds suggests that the length of the alkyl chain enhances the interaction between the inhibitor and the area of the active site corresponding to the C(3) area of the steroid backbone, thereby increasing potency.

N-UREIDOALKYL-AMINO COMPOUNDS AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present application describes modulators of chemokine receptors of formula (I), or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

Direct synthesis of 3-arylpropionic acids by tetraphosphine/palladium catalysed Heck reactions of aryl halides with acrolein ethylene acetal

Through the use of [PdCl(C3H5)]2/Cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides undergoes Heck reaction with acrolein ethylene acetal. With this acetal, the selective formation of 3-arylpropionic acids/esters was observed. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides. Graphical Abstract.