35553-92-5

Usage

Uses

Used in Flavoring and Fragrance Industry:
ETHYL 3-METHOXYPHENYLACETATE is used as a flavoring and fragrance ingredient for its pleasant smell, adding a unique and appealing scent to various products.
Used in Perfumery:
In the perfumery industry, ETHYL 3-METHOXYPHENYLACETATE is used as a fragrance ingredient to provide a slightly sweet, floral, and fruity aroma, contributing to the creation of complex and attractive scents in perfumes.
Used in Cosmetics:
ETHYL 3-METHOXYPHENYLACETATE is used in cosmetics as a fragrance ingredient to impart a pleasant and exotic scent to products, enhancing their sensory appeal and consumer experience.
Used in Food Industry:
In the food industry, ETHYL 3-METHOXYPHENYLACETATE is used as a flavoring ingredient to add a slightly sweet, floral, and fruity taste to food items, improving their overall flavor profile and consumer enjoyment.

InChI:InChI=1/C11H14O3/c1-3-14-11(12)8-9-5-4-6-10(7-9)13-2/h4-7H,3,8H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 1798-09-0 m-methoxyphenylacetic acid 
• 529-28-2 4-iodoanisol 
• 26954-26-7 ethyl lithioacetate 
• 6971-51-3 3-methoxybenzyl alcohol 
• 100-83-4 meta-hydroxybenzaldehyde 
• 824-98-6 m-methoxybenzyl chloride 
• 2398-37-0 3-methoxyphenyl bromide 
• 105-53-3 diethyl malonate 
• 6148-64-7 ethyl potassium malonate 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 10365-98-7 3-methoxyphenylboronic acid 
• 623-33-6 glycine ethyl ester hydrochloride 

Downstream Products

• 5020-41-7 2-(3-methoxyphenyl)-ethanol 
• 88488-70-4 1-(3-methoxy-phenyl)-pentane-2,4-dione 
• 130754-15-3 ethyl 2-fluoro-2-(3-methoxyphenyl)acetate 
• 115981-89-0 ethyl 2-(m-methoxyphenyl)-3-hydroxybutanoate 
• 50874-07-2 2-(3-methoxyphenyl)malonic acid diethyl ester 
• 105166-35-6 2-(3-methoxyphenyl)propanoic acid ethyl ester 
• 87942-68-5 4-(3-Methoxyphenyl)-2-methyl-3-oxobutannitril 
• 63476-11-9 ethyl (5-methoxy-2-acethylphenyl)acetate 
• 184871-46-3 (3-Methoxy-phenyl)-phenylsulfanyl-acetic acid ethyl ester 
• 92848-09-4 ethyl 3-oxo-2-(m-methoxyphenyl)propanoate 

Relevant academic research and scientific papers

Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids

A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

COMPOUNDS FOR USE IN TREATING NEUROLOGICAL DISORDERS

Provided are methods for treating neurological disorders using compounds of Formula (I), and pharmaceutically acceptable salts and compositions thereof.

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.

P300/CBP HAT INHIBITORS

Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with histone acetyltransferase (HAT).

Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O

A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

A novel serine racemase inhibitor suppresses neuronal over-activation in vivo

Serine racemase (SRR) is an enzyme that produces D-serine from L-serine. D-Serine acts as an endogenous coagonist of NMDA-type glutamate receptors (NMDARs), which regulate many physiological functions. Over-activation of NMDARs induces excitotoxicity, which is observed in many neurodegenerative disorders and epilepsy states. In our previous works on the generation of SRR gene knockout (Srr-KO) mice and its protective effects against NMDA- and Aβ peptide-induced neurodegeneration, we hypothesized that the regulation of NMDARs’ over-activation by inhibition of SRR activity is one such therapeutic strategy to combat these disease states. In the previous study, we performed in silico screening to identify four compounds with inhibitory activities against recombinant SRR. Here, we synthesized 21 derivatives of candidate 1, one of four hit compounds, and performed screening by in vitro evaluations. The derivative 13J showed a significantly lower IC50 value in vitro, and suppressed neuronal over-activation in vivo.

Mechanistic studies on gold-catalyzed direct arene c-h bond functionalization by carbene insertion: The coinage-metal effect

The catalytic functionalization of the Csp2-H bond of benzene by means of the insertion of the CHCO2Et group from ethyl diazoacetate (N2= CHCO2Et) has been studied with the series of coinage-metal complexes IPrMCl (IPr = 1,3-bis- (diisopropylphenyl)imidazol-2-ylidene) and NaBArF 4 (BArF 4 = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate). For Cu and Ag, these examples constitute the first use of such metals toward this transformation, which also provides ethyl cyclohepta-2,4,6-trienecarboxylate as a byproduct from the so-called Buchner reaction. In the case of methyl-substituted benzenes, the reaction exclusively proceeds onto the aromatic ring, the Csp3-H bond remaining unreacted. A significant coinage-metal effect has been observed, since the gold catalyst favors the formation of the insertion product into the Csp2-H bond whereas copper and silver preferentially induce the formation of the cycloheptatriene derivative. Experimental studies and theoretical calculations have explained the observed selectivity in terms of the formation of a common Wheland intermediate, resembling an electrophilic aromatic substitution, from which the reaction pathway evolves into two separate routes to each product.