3724-19-4

Usage

Uses

Used in Coordination Polymers:
3-Pyridinepropanoic acid is used as a ligand for the preparation of new coordination polymers of Ag, Cu, and Zn. It reacts with AgNO3, Cu(NO3)2·6H2O, and Zn(NO3)2·6H2O in MeOH to form these polymers, which have potential applications in various fields due to their unique properties.
Used in Hydrothermal Synthesis:
In the hydrothermal synthesis process, 3-Pyridinepropanoic acid is used to create coordination polymers such as [Zn(PPA)2(H2O)2]n and [Cd(PPA)2]n. These polymers can be utilized in different industries, including materials science and pharmaceuticals, due to their distinct characteristics.
Used in Rare-Earth Ion Chelation:
3-Pyridinepropanoic acid serves as a bidentate chelating agent for the chelation of rare-earth ions, specifically Eu3+ and Tb3+. This chelation process enhances the fluorescence properties of sol-gels, making them more suitable for applications in optical devices and sensors.

Upstream product

• 64107-54-6 3-pyridin-3-yl-propionic acid ethyl ester 
• 2859-67-8 3-(3-pyridyl)propan-1-ol 
• 6283-81-4 3-oxo-3-pyridin-3-yl-propionic acid ethyl ester 
• 7440-44-0 pyrographite 
• 1121-55-7 3-vinylpyridine 
• 201230-82-2 carbon monoxide 
• 500-22-1 3-pyridinecarboxaldehyde 
• 81124-48-3 methyl (E)-3-(3-pyridyl)acrylate 
• 626-55-1 3-Bromopyridine 
• 84199-98-4 methyl 3-(3-pyridyl)propanoate 
• 3984-22-3 2-vinyl-1,3-dioxolane 
• 1126-74-5 3-(pyridin-3-yl)acrylic acid 
• 99356-83-9 (E)-3-(2-carboxyvinyl)pyridine 1-oxide 
• 19337-97-4 trans-3-(3-pyridyl)acrylic acid 

Downstream Products

• 84199-98-4 methyl 3-(3-pyridyl)propanoate 
• 107755-78-2 N-[3-(pyridin-3-yl)propionyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine 
• 205236-52-8 (S)-4-[(S)-3-[4-(Di-tert-butoxy-phosphoryloxy)-phenyl]-2-(3-pyridin-3-yl-propionylamino)-propionylamino]-4-dipentylcarbamoyl-butyric acid tert-butyl ester 
• 104261-69-0 1-hydroxy-3-(3-pyridyl)propylidene-1,1-bisphosphonic acid 
• 944997-60-8 α-cyclohexyl-N-[1-[1-oxo-3-(3-pyridinyl)propyl]-4-piperidinyl]benzeneacetamide 
• 200867-93-2 N-[3-(1-benzylpiperidin-4-yloxy)-propyl]-3-(pyridin-3-yl)-propionamide 
• 184105-43-9 (3S,4S)-3-{N-(3-pyrid-3-yl-propionoyl)-L-phenylalanyl}-amino-4-acetoxy-azetidin-2-one 
• 1132660-87-7 t-butyl 3-{4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinolin-2-yl)-2-[(3-pyridin-3-ylpropanoyl)amino]phenoxy}propylcarbamate 
• 1384184-08-0 N-[5-(4-methoxy-phenylsulfanyl)-thiazol-2-yl]-3-pyridin-3-yl-propionamide 
• 1081112-31-3 2-[2-(pyridin-3-yl)ethyl]-1-{3-[4-(3-acetamidophenyl)piperidin-1-yl]propyl}-1H-benzimidazole 
• 6312-09-0 3-(2-phenylethyl)pyridine 
• 147918-36-3 3-(but-3-yn-1-yl)pyridine 

Relevant academic research and scientific papers

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

A temperature switchable pyridyl-zinc(II) side arm porphyrin with functionality for surface immobilisation

A pyridyl side arm porphyrin incorporating C10 alkyl chains at the periphery of the porphyrin suitable for surface immobilisation on HOPG has been synthesised and tested for two state switching in solution. Temperature switching, involving reversible complexation of a covalently appended pyridyl side arm to the Zn(II) porphyrin, was comprehensively characterised by using variable temperature 1H NMR (-30 to +100°C) and UV-vis (10 to 90°C) in toluene. Molecular modelling assisted in understanding strain within the complex.

An Anionic, Chelating C(sp3)/NHC ligand from the Combination of an N-heterobicyclic Carbene and Barbituric Heterocycle

The coordination chemistry of the anionic NHC1-based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) platform substituted at the C5 position by an anionic barbituric heterocycle was studied with d6(Ru(II), Mn(I)) and d8(Pd(II), Rh(I), Ir(I), Au(III)) transition-metal centers. While the anionic barbituric heterocycle is planar in the zwitterionic NHC precursor 1·H, NMR spectroscopic analyses supplemented by X-ray diffraction studies evidenced the chelating behavior of ligand 1-through the carbenic and the malonic carbon atoms in all of the complexes, resulting from a deformation of the lateral barbituric heterocycle. The complexes were obtained by reaction of the free carbene with the appropriate metal precursor, except for the Au(III) complex 10, which was obtained by oxidation of the antecedent gold(I) complex [AuCl(1)]?with PhICl2as an external oxidant. During the course of the process, the kinetic gold(I) intermediate 9 resulting from the oxidation of the malonic carbon of the barbituric moiety was isolated upon crystallization from the reaction mixture. The νCOstretching frequencies recorded for complex [Rh(1)(CO)2] (5) demonstrated the strong donating character of the malonate-C(sp3)/NHC ligand 1-. The ruthenium complex [Ru(1)Cl(p-cymene)] (11) was implemented as a precatalyst in the dehydrogenative synthesis of carboxylic acid derivatives from primary alcohols and exhibited high activities at low catalyst loadings (25-250 ppm) and a large tolerance toward functional groups.

Regioselectivity inversion tuned by iron(iii) salts in palladium-catalyzed carbonylations

Impactful regioselectivity control is crucial for cost-effective chemical synthesis. By using cheap and abundant iron(iii) salts, the hydroxycarbonylations of both aromatic and aliphatic alkenes were significantly enhanced in both reactivity and selectivity (iso/n or n/iso up to >99:1). Moreover, Pd-catalyzed carbonylation selectivity can be switched from branched to linear by using different Fe(iii) salts. In addition, similar results were obtained for the carbonylation of secondary alcohols.

Strategic Approach to 8-Azacoumarins

8-Azacoumarins have emerged as a promising class of compounds but are rarely explored due to challenging access. A novel, general, and practical method is provided for this class of compounds. The key lactonization step employs trans-acrylic acid attached pyridine N-oxides as the starting material, with acetic anhydride as both the activation agent and the solvent. Multiple transformations were involved in this reaction, including conjugate addition, nucleophilic aromatic substitution, and elimination. These studies provide the basis for access to 8-azacoumarins, enabling future work including the discovery and development of novel coumarin-type drugs, fluorescent probes, photolabile protecting groups, and other active molecules.

A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism

Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.

Discovery of new C3aR ligands. Part 2: Amino-piperidine derivatives

The synthesis and structure-activity relationships against the C3a receptor of a series of substituted aminopiperidine derivatives are reported. DMPK properties and functional activities of selected compounds are described. The compounds obtained are the first non-arginine ligands of C3aR.

The 3-(3-pyridine)propionyl anchor group for protease-catalyzed resolutions: p-toluenesulfinamide and sterically hindered secondary alcohols

Compared to an acetyl acyl group, the 3-(3-pyridine)propionyl group increases substrate binding to many proteases and substrate solubility in water, thereby increasing the rates of protease-catalyzed reactions. For example, proteases reacted up to six hundred-fold faster with the 3-(3-pyridine)propionyl ester of 1-phenylethanol than with the corresponding acetate ester. In addition, the 3-(3-pyridine)propionyl group enables a simple, mild acid extraction to separate the remaining starting material and product. To demonstrate the synthetic usefulness of this strategy, we resolved multi-gram quantities of (R)- and (S)-p-toluenesulfinamide with α-chymotrypsin and gram quantities of (R)- and (S)-2,2-dimethylcyclopentanol with subtilisin Carlsberg. The 3-(3-pyridyl)propionyl group was better for these resolutions than the corresponding acetate or dihydrocinnamate because it decreased the reaction time due to increased reactivity, decreased the reaction volume due to increased substrate solubility and enabled purification without chromatography. Molecular modeling suggests the enantioselectivity of α-chymotrypsin toward (R)-p-toluenesulfinamide is high (E = 52) because of a favorable hydrophobic interaction between the p-tolyl group of the fast-reacting (R)-enantiomer and leaving group pocket. The enantioselectivity of subtilisin Carlsberg toward (S)-2,2-dimethylcyclopentanol is high (E = 43) because the large substituent (the 2,2-dimethyl quaternary carbon) of the slow-reacting (R)-enantiomer cannot fit in the S1′ leaving group pocket.

PYRAZOLONAPHTHYRIDINE DERIVATIVE

The target is to provide PDE IV inhibitors which have a highly potent anti-asthmatic and/or COPD-prophylactic/therapeutic profile with unexpectedly excellent safety. A compound of the formula (1): wherein A is phenyl, pyridyl, 1-oxypyridyl, or thienyl, which may be unsubstituted or optionally substituted with one or more members selected from the group consisting of hydroxyl, halogen, cyano, nitro, lower alkyl, lower alkoxy, lower alkylcarbonyloxy, amino, carboxyl, lower alkoxycarbonyl, carboxy-lower alkylene, lower alkoxycarbonyl-lower alkylene, lower alkylsulfonyl, lower alkylsulfonylamino, and ureido; R1 is a group selected from the group consisting of hydrogen, hydroxyl, halogen, cyano, nitro, lower alkoxy, amino, carboxyl, and lower alkoxycarbonyl; R2 is hydrogen or lower alkyl; and m is an integer of 1 to 3; or a pharmaceutically acceptable salt thereof, possesses highly excellent PDE IV-specific inhibitory actions and is useful as an anti-asthmatic drug and/or a prophylactic/therapeutic drug for COPD with high safety.

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.