24470-14-2

Usage

Uses

Used in Asymmetric Synthesis:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid is used as a chiral auxiliary in asymmetric synthesis for enhancing the selectivity and yield of enantiomerically pure compounds. Its ability to induce chirality in the products makes it a valuable tool in the synthesis of complex organic molecules.
Used in Organic Synthesis:
As a building block in organic synthesis, (S)-(+)-2-(4'-methoxyphenyl)propanoic acid is employed for constructing a wide range of organic compounds, including pharmaceuticals and agrochemicals. Its versatile structure allows for various functional group transformations and incorporation into more complex molecules.
Used in Pharmaceutical Production:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid is used as a key component in the production of pharmaceuticals. Its potential antioxidant, anti-inflammatory, and analgesic properties make it a promising candidate for the development of new drugs targeting various medical conditions.
Used in Agrochemicals:
In the agrochemical industry, (S)-(+)-2-(4'-methoxyphenyl)propanoic acid is used as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique properties contribute to the development of effective and targeted agricultural products.
Used in Antioxidant Applications:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid has been studied for its potential antioxidant properties, which could be beneficial in the development of products that protect cells from oxidative damage, a common factor in many diseases.
Used in Anti-inflammatory Applications:
(S)-(+)-2-(4'-methoxyphenyl)propanoic acid's potential anti-inflammatory properties make it a candidate for the development of new treatments for inflammatory conditions, such as arthritis and other autoimmune diseases.
Used in Analgesic Applications:
As a potential analgesic, (S)-(+)-2-(4'-methoxyphenyl)propanoic acid could be used in the development of new pain-relieving medications, offering alternative options for patients in need of effective pain management.

Upstream product

• 942-54-1 2-(4-methoxyphenyl)propanoic acid 
• 31007-06-4 2-(4-methoxyphenyl)propionitrile 
• 62784-66-1 bis(1-naphthyl)methanol 
• 637-69-4 4-Methoxystyrene 
• 201230-82-2 carbon monoxide 
• 93397-63-8 (S)-4-methoxy-β-methylbenzeneethanol 
• 252058-33-6 2-(4-methoxyphenyl)propanal 
• 100-66-3 methoxybenzene 
• 117177-66-9 2-(4-methoxyphenyl)-2-oxoacetyl chloride 
• 1429641-12-2 C₁₀H₉ClO₂ 
• 51747-42-3 2-(4-methoxy-phenyl)-acrylic acid 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 50415-73-1 methyl 2-(4-methoxyphenyl)propionate 
• 2901-41-9 2-(4-methoxyphenyl)ethyl propionate 

Downstream Products

• 129411-26-3 (S)-N-Butyl-2-(4-hydroxy-phenyl)-N-methyl-propionamide 
• 143589-99-5 (1S)-N-benzyloxycarbonyl-1-(4-methoxy-phenyl)ethylamine 
• 111197-94-5 methyl (S)-2-(4-methyoxyphenyl)propionate 
• 129411-30-9 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(S)-1-((S)-1-methyl-heptyloxycarbonyl)-ethyl]-phenyl ester 
• 129411-31-0 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(S)-1-((R)-1-methyl-heptyloxycarbonyl)-ethyl]-phenyl ester 
• 129411-28-5 4'-Decyloxy-3'-fluoro-biphenyl-4-carboxylic acid 4-((S)-1-butoxycarbonyl-ethyl)-phenyl ester 
• 129411-32-1 4'-Octyloxy-biphenyl-4-carboxylic acid 4-[(S)-1-(butyl-methyl-carbamoyl)-ethyl]-phenyl ester 
• 129411-33-2 4'-((R)-1-Methyl-heptyloxy)-biphenyl-4-carboxylic acid 4-[(S)-1-(butyl-methyl-carbamoyl)-ethyl]-phenyl ester 
• 129411-29-6 4'-((R)-1-Methyl-heptyloxy)-biphenyl-4-carboxylic acid 4-((S)-1-butoxycarbonyl-ethyl)-phenyl ester 
• 132786-62-0 (S)-2-(4-Hydroxy-phenyl)-propionic acid (S)-1-methyl-heptyl ester 
• 132786-63-1 (S)-2-(4-Hydroxy-phenyl)-propionic acid (R)-1-methyl-heptyl ester 

Relevant academic research and scientific papers

Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids

Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.

Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP?, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP? is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (S)-Profens and Profenols

The biocatalytic asymmetric disproportionation of aldehydes catalyzed by horse liver alcohol dehydrogenase (HLADH) was assessed in detail on a series of racemic 2-arylpropanals. Statistical optimization by means of design of experiments (DoE) allowed the identification of critical interdependencies between several reaction parameters and revealed a specific experimental window for reaching an ′optimal compromise′ in the reaction outcome. The biocatalytic system could be applied to a variety of 2-arylpropanals and granted access in a redox-neutral manner to enantioenriched (S)-profens and profenols following a parallel interconnected dynamic asymmetric transformation (PIDAT). The reaction can be performed in aqueous buffer at ambient conditions, does not rely on a sacrificial co-substrate, and requires only catalytic amounts of cofactor and a single enzyme. The high atom-efficiency was exemplified by the conversion of 75 mM of rac-2-phenylpropanal with 0.03 mol% of HLADH in the presence of ～0.013 eq. of oxidized nicotinamide adenine dinucleotide (NAD+), yielding 28.1 mM of (S)-2-phenylpropanol in 96% ee and 26.5 mM of (S)-2-phenylpropionic acid in 89% ee, in 73% overall conversion. Isolated yield of 62% was obtained on 100 mg-scale, with intact enantiopurities. (Figure presented.).

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Ferrocenyl chiral bisphosphorus ligands for highly enantioselective asymmetric hydrogenation via noncovalent ion pair interaction

A new class of ferrocenyl chiral bisphosphorus ligand, Wudaphos, was developed, and exhibits excellent ee and activity (ee up to 99%, TON up to 20000) for the asymmetric hydrogenation of both 2-aryl and 2-alkyl acrylic acids through ion pair noncovalent interaction under base free and mild reaction conditions. Well-known anti-inflammatory drugs such as naproxen and ibuprofen together with the intermediate for the preparation of Roche ester and some bioactive compounds were also efficiently obtained with excellent ee. Control experiments were conducted and revealed that the ion pair noncovalent interaction and chain length played important roles.

Chiral diphosphine ligand in asymmetric hydrogenation thereof and related application of the catalyst in the reaction (by machine translation)

The invention discloses a chiral diphosphine ligand based on ferrocene skeleton in asymmetric hydrogenation thereof and related application of the catalyst in the reaction. This kind of novel chiral diphosphine ligand has as the general formula I The structure of the shown, wherein R 1 can be is methyl, phenyl, tert-butyl, hydroxy, etc.. R 2 can be ethyl, phenyl, cyclohexyl, methyl phenyl, tert-butyl, 3,5-dimethyl phenyl, 3,5-di-tert-butyl phenyl, 3,5-di-tert-butyl-4-methoxybenzene, 2,6-dimethoxyphenyl, 2,6-dimethyl phenyl, anthryl. At the same time, two phosphine atom bridged between the can is phenyl, naphthyl, alkyl or the like. At the same time, this invention has disclosed this kind of novel chiral diphosphine ligand synthesis and in preparation of chiral pharmaceutical ibuprofen and a naproxen, and the like. (by machine translation)

Enantiospecific, regioselective cross-coupling reactions of secondary allylic boronic esters

An original syn: The first enantioselective Suzuki-Miyaura cross-coupling of chiral, enantioenriched secondary allylic boronic esters is described (see scheme; DME=dimethoxyethane, Bpin = pinacolboryl, dba = dibenzylideneacetone). Mechanistic studies show that the reactions proceed via γ-selective transmetalation followed by reductive elimination. The reaction provides the first independent confirmation that the transmetalation of boronic esters proceeds via a syn pathway. Copyright

Kinetic resolution of racemic α-arylalkanoic acids with achiral alcohols via the asymmetric esterification using carboxylic anhydrides and acyl-transfer catalysts

A variety of optically active carboxylic esters are produced by the kinetic resolution of racemic α-substituted carboxylic acids using achiral alcohols, aromatic or aliphatic carboxylic anhydrides, and chiral acyl-transfer catalysts. The combination of 4-methoxybenzoic anhydride (PMBA) or pivalic anhydride with the modified benzotetramisole-type catalyst ((S)-β-Np-BTM) is the most effective for promotion of the enantioselective coupling reaction between racemic carboxylic acids and a novel nucleophile, bis(α-naphthyl) methanol, to give the corresponding esters with high ees. This protocol was successfully applied to the production of nonracemic nonsteroidal anti-inflammatory drugs from racemic compounds utilizing the transacylation process to generate the mixed anhydrides from the acid components with the suitable carboxylic anhydrides.

METHOD FOR PRODUCING OPTICALLY ACTIVE ESTER AND METHOD FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID

Disclosed is a method for producing an optically active ester by highly selectively esterifying one enantiomer of a racemic carboxylic acid, while producing an optically active carboxylic acid which is the other enantiomer. An optically active ester is produced while producing an optically active carboxylic acid at the same time by reacting a racemic carboxylic acid with a specific alcohol or phenol derivative in the presence of benzoic anhydride or a derivative thereof and a catalyst such as tetramisole or benzotetramisole, thereby selectively esterifying one enantiomer of the racemic carboxylic acid.

Kinetic resolution of racemic carboxylic acids using achiral alcohols by the promotion of benzoic anhydrides and tetramisole derivatives: Production of chiral nonsteroidal anti-inflammatory drugs and their esters

A variety of optically active carboxylic esters were produced by kinetic resolution of racemic carboxylic acids by using achiral alcohols, benzoic anhydrides, and Birman's tetramisole-type catalysts. Bis(α-naphthyl) methanol is a very effective reagent for producing the corresponding esters with high ee values in the presence of 4-methoxybenzoic anhydride (PMBA) as the coupling reagent by promotion of benzotetramisole derivatives (BTM, α-Np-BTM, and β-Np-BTM). This protocol directly provides chiral carboxylic esters from free carboxylic acids and achiral alcohols by utilizing a transacylation process to generate the mixed anhydrides from the acid components with benzoic anhydride derivatives in the presence of chiral catalysts. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.