50845-77-7

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2-[(4-methoxyphenyl)amino]acetate is used as a reactant for the synthesis of amino acid derivatives, which are crucial in the development of new pharmaceutical compounds. ethyl 2-[(4-methoxyphenyl)amino]acetate plays a significant role in the copper-catalyzed cross-dehydrogenative coupling of ketones with glycine derivatives, a method that allows for the efficient and selective formation of these important building blocks in drug discovery and medicinal chemistry.
Used in Chemical Research:
In the field of chemical research, ethyl 2-[(4-methoxyphenyl)amino]acetate serves as a valuable intermediate for the preparation of various organic compounds and materials. Its unique structure allows for further functionalization and modification, making it a useful tool for exploring new chemical reactions and developing novel synthetic pathways.
Used in Material Science:
Ethyl 2-[(4-methoxyphenyl)amino]acetate may also find applications in material science, particularly in the development of new polymers and materials with specific properties. ethyl 2-[(4-methoxyphenyl)amino]acetate's ability to form amino acid derivatives can contribute to the creation of biocompatible materials, sensors, or other advanced materials with tailored characteristics for various applications.

Upstream product

• 104-94-9 4-methoxy-aniline 
• 105-39-5 chloroacetic acid ethyl ester 
• 64-17-5 ethanol 
• 22094-69-5 N-(4-methoxyphenyl)glycine 
• 100-17-4 para-methoxynitrobenzene 
• 623-33-6 glycine ethyl ester hydrochloride 
• 459-73-4 GlyOEt*HCl 
• 1152-75-6 N,N'-bis(4-methoxyphenyl)iminoformamide 
• 105-36-2 ethyl bromoacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 7664-93-9 sulfuric acid 
• 109-92-2 ethyl vinyl ether 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 924-44-7 glyoxylic acid ethyl ester 

Downstream Products

• 1352662-70-4 diethyl 2-acetyl-3-(4-methoxyphenylamino)-2-methylsuccinate 
• 1352662-67-9 benzyl 1-(2-ethoxy-1-(4-methoxyphenylamino)-2-oxoethyl)-2-oxocyclopentanecarboxylate 
• 1352662-72-6 4-ethyl 1-methyl 3-(4-methoxyphenylamino)-2-methyl-2-propionylsuccinate 
• 1352662-68-0 allyl 1-(2-ethoxy-1-(4-methoxyphenylamino)-2-oxoethyl)-2-oxocyclopentanecarboxylate 
• 1352662-56-6 ethyl 1-(1-(4-methoxyphenylamino)-2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate 
• 124156-21-4 ethyl (4-methoxyphenylimino)acetate 
• 1146728-31-5 tert-butyl-1-(2-ethoxy-1-(4-methoxyphenylamino)-2-oxo-ethyl)-2-oxo-cyclopentyl carboxylate 
• 1352662-65-7 isopropyl 1-(2-ethoxy-1-(4-methoxyphenylamino)-2-oxoethyl)-2-oxocyclopentanecarboxylate 

Relevant academic research and scientific papers

On the Regioselectivity of 4-Nitroanisole Photosubstitution with Primary Amines. A Mechanistic and Theoretical Study

4-Nitroanisole photoreacts with n-hexylamine and ethyl glycinate, giving rise to regioselective methoxy and nitro group photosubstitution, respectively.Mechanistic evidence indicates that the latter is produced through a SN23Ar*

Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines

A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst CsPbBr3 can be simply recovered from the reaction mixture and reused at least five times without an obvious reduction in its photocatalytic reactivity, exhibiting a high catalyst economic feature.

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

Design, synthesis and biological evaluation of oxime lacking Psammaplin inspired chemical libraries as anti-cancer agents

In this study, we attempted the chemical simplification of Psammaplin (PsA), while retaining its activity in vitro. Inspired by the previous Structure Activity Relationship (SAR) studies on various PsA analogues and relying on the fact that oxime is metabolically unstable, we initially designed and synthesized a diverse library of PsA analogues and evaluated for cytotoxic activity. Among 32 compounds of Psammaplin analogues synthesized, the compound 10b was almost equally active as parent Psammaplin in vitro.

Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions

In this work, a visible-light-induced oxidative α-alkylation of glycine derivatives with ethers has been developed in the presence of catalytic Eosin Y. Under the blue light of a 3 W LED, a range of α-etherized glycine derivatives, including α-amino esters, α-amino ketones and α-amino amides, were achieved with good to excellent yields and functional group tolerance with tert-butyl hydroperoxide (TBHP) as oxidant at ambient temperature. The operationally easy procedure provides an economical, metal-free, and mild alternative for the synthesis of the α-etherized glycine derivatives.

Molecular Oxygen-Mediated Radical Alkylation of C(sp3)-H Bonds with Boronic Acids

A direct and site-specific alkylation of (sp3)C-H bond with aliphatic boronic acid was achieved. By simply heating glycinates and amines together with alkylboronic acids under an oxygen atmosphere, a variety of unnatural α-amino acids and peptides could b

Direct, Site-Selective and Redox-Neutral α-C?H Bond Functionalization of Tetrahydrofurans via Quantum Dots Photocatalysis

As one of the most ubiquitous bulk reagents available, the intrinsic chemical inertness of tetrahydrofuran (THF) makes direct and site-selective C(sp3)?H bond activation difficult, especially under redox neutral condition. Here, we demonstrate that semiconductor quantum dots (QDs) can activate α-C?H bond of THF via forming QDs/THF conjugates. Under visible light irradiation, the resultant alkoxyalkyl radical directly engages in radical cross-coupling with α-amino radical from amino C?H bonds or radical addition with alkene or phenylacetylene, respectively. In contrast to stoichiometric oxidant or hydrogen atom transfer reagents required in previous studies, the scalable benchtop approach can execute α-C?H bond activation of THF only by a QD photocatalyst under redox-neutral condition, thus providing a broad of value added chemicals starting from bulk THFs reagent.

Selective carbene transfer to amines and olefins catalyzed by ruthenium phthalocyanine complexes with donor substituents

Electron-rich ruthenium phthalocyanine complexes were evaluated in carbene transfer reactions from ethyl diazoacetate (EDA) to aromatic and aliphatic olefins as well as to a wide range of aromatic, heterocyclic and aliphatic amines for the first time. It was revealed that the ruthenium octabutoxyphthalocyanine carbonyl complex [(BuO)8Pc]Ru(CO) is the most efficient catalyst converting electron-rich and electron-poor aromatic olefins to cyclopropane derivatives with high yields (typically 80-100%) and high TON (up to 1000) under low catalyst loading and nearly equimolar substrate/EDA ratio. This catalyst shows a rare efficiency in the carbene insertion into amine N-H bonds. Using a 0.05 mol% catalyst loading, a high amine concentration (1 M) and 1.1 eq. of EDA, a number of structurally divergent amines were selectively converted to mono-substituted glycine derivatives with up to quantitative yields and turnover numbers reaching 2000. High selectivity, large substrate scope, low catalyst loading and practical reaction conditions place [(BuO)8Pc]Ru(CO) among the most efficient catalysts for the carbene insertion into amines.

Unnatural α-Amino Acid Synthesized through α-Alkylation of Glycine Derivatives by Diacyl Peroxides

We have developed a protocol for catalyst- and additive-free α-alkylation reactions of glycine derivatives with diacyl peroxides, which proceed by a pathway involving addition of alkyl radicals to imine intermediates. The diacyl peroxide substrate acts as both alkylation agent and oxidizing agent, which means it is atom-economical. It was applied to various glycine derivatives, dipeptides, and a 3,4-dihydroquinoxalin-2(1H)-one derivative and could be carried out on a gram scale, indicating its utility for late-stage functionalization.