6274-50-6

Usage

Uses

Used in Organic Synthesis:
2-(4-Methoxy-phenyl)-2-Methyl-propionicacidMethylester is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for the formation of new bonds and reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2-(4-Methoxy-phenyl)-2-Methyl-propionicacidMethylester is employed as a building block for the development of new drugs. Its chemical properties enable the creation of novel drug candidates with potential therapeutic benefits, contributing to the advancement of medicine and healthcare.
Used in Research and Development:
2-(4-Methoxy-phenyl)-2-Methyl-propionicacidMethylester is utilized in research laboratories for the exploration of new chemical reactions and the synthesis of innovative compounds. Its versatility and reactivity make it an essential tool for scientists working in the fields of organic chemistry, medicinal chemistry, and materials science.
Used in Industrial Applications:
Beyond its use in organic synthesis and pharmaceutical production, 2-(4-Methoxy-phenyl)-2-Methyl-propionicacidMethylester finds applications in various industrial sectors. Its properties, such as solubility and reactivity, make it suitable for the development of new materials, coatings, and other industrial products.
It is important to handle 2-(4-Methoxy-phenyl)-2-Methyl-propionicacidMethylester with care, as it is a potential irritant to the skin, eyes, and respiratory system. Proper safety measures should be taken during its use to ensure the well-being of individuals working with this chemical compound.

InChI:InChI=1/C12H16O3/c1-12(2,11(13)15-4)9-5-7-10(14-3)8-6-9/h5-8H,1-4H3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 547-63-7 Methyl isobutyrate 
• 67-56-1 methanol 
• 2955-46-6 2-(4-methoxyphenyl)-2-methylpropanoic acid 
• 623-12-1 4-chloromethoxybenzene 
• 696-62-8 para-iodoanisole 
• 50415-73-1 methyl 2-(4-methoxyphenyl)propionate 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 40919-14-0 2-(4-methoxy-phenyl)-2-methyl-propionyl chloride 
• 731015-44-4 methyl 2-(3-formyl-4-hydroxyphenyl)-2-methylpropanoate 
• 123342-40-5 methyl 2-(4-hydroxyphenyl)-2-methylpropanoate 
• 2955-46-6 2-(4-methoxyphenyl)-2-methylpropanoic acid 
• 1421838-11-0 N-(bis(4-fluorophenyl)methyl)-2-(4-hydroxyphenyl)-2-methylpropanamide 
• 29913-51-7 2-methyl-2-(p-hydroxyphenyl)-propionic acid 
• 32445-98-0 2,3-bis(4-methoxyphenyl)-2,3-dimethylbutane 
• 32454-31-2 2-p-Methoxyphenyl-2-methyl-1-methylthiomethoxypropan 
• 85385-44-0 4-(1-deuterio-1-methylethyl)anisole 
• 4132-48-3 1-methoxy-4-(1-methylethyl)benzene 
• 32454-14-1 2-(4-methoxyphenyl)-2-methylpropanal 
• 63045-26-1 2-(3-Chloro-4-methoxy-phenyl)-2-methyl-propionic acid methyl ester 
• 32454-29-8 2-(4-methoxy-phenyl)-2-methyl-propan-1-ol 

Relevant academic research and scientific papers

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.

α-Arylation of Esters and Ketones Enabled by a Bench-Stable Pd(I) Dimer Catalyst

A procedure for the α-arylation of α,α-disubstituted esters and ketones to generate quaternary carbon centers is described. The developed protocol is operationally simple and employs an air- and moisture-stable dinuclear Pd(I) complex [Pd(μ-I)(P t -Bu 3)] 2 to mediate selective α-arylation of aromatic C-I/Br bonds in the presence of aromatic C-Cl and/or C-OTf sites.

Nickel-Catalyzed oxidative coupling of unactivated C(sp3)-H bonds in aliphatic amides with terminal alkynes

In this work, we demonstrated Ni-catalyzed oxidative coupling of unactivated C(sp3)-H bonds with terminal alkynes for construction of C(sp3)-C(sp) bonds to synthesize alkyl-substituted internal alkynes. Different amides exhibited good compatibility. Preliminary mechanistic studies were conducted to account for this alkynylation.

COMPOUNDS AND METHODS

The present invention relates to novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORy.

COMPOUNDS AND METHODS

The present invention relates to novel retinoid-reiated orphan receptor gamma (RORy) modulators and their use in the treatment of diseases mediated by RORy.

One-electron oxidation of 2-(4-methoxyphenyl)-2-methylpropanoic and 1-(4-methoxyphenyl)cyclopropanecarboxylic acids in aqueous solution. The involvement of radical cations and the influence of structural effects and pH on the side-chain fragmentation reactivity

(Chemical Equation Presented) A product and time-resolved kinetic study on the one-electron oxidation of 2-(4-methoxyphenyl)-2-methylpropanoic acid (2), 1-(4-methoxyphenyl)cyclopropanecarboxylic acid (3), and of the corresponding methyl esters (substrates 4 and 5, respectively) has been carried out in aqueous solution. With 2, no direct evidence for the formation of an intermediate radical cation 2?+ but only of the decarboxylated 4-methoxycumyl radical has been obtained, indicating either that 2?+ is not formed or that its decarboxylation is too fast to allow detection under the experimental conditions employed (k > 1 × 107 s -1). With 3, oxidation leads to the formation of the corresponding radical cation 3?+ or radical zwitterion -3 ?+ depending on pH. At pH 1.0 and 6.7, 3?+ and -3?+ have been observed to undergo decarboxylation as the exclusive side-chain fragmentation pathway with rate constants k = 4.6 × 103 and 2.3 × 104 s-1, respectively. With methyl esters 4 and 5, direct evidence for the formation of the corresponding radical cations 4?+ and 5?+ has been obtained. Both radical cations have been observed to display a very low reactivity and an upper limit for their decay rate constants has been determined as k 3 s-1. Comparison between the one-electron oxidation reactions of 2 and 3 shows that the replacement of the C(CH3)2 moiety with a cyclopropyl group determines a decrease in decarboxylation rate constant of more than 3 orders of magnitude. This large difference in reactivity has been qualitatively explained in terms of three main contributions: substrate oxidation potential, stability of the carbon-centered radical formed after decarboxylation, and stereoelectronic effects. In basic solution, -3?+ and 5 ?+ have been observed to react with -OH in a process that is assigned to the -OH-induced ring-opening of the cyclopropane ring, and the corresponding second-order rate constants (k-OH) have been obtained. With -3?+, competition between decarboxylation and -OH-induced cyclopropane ring-opening is observed at pH ≥ 10, with the latter process that becomes the major fragmentation pathway around pH 12.

Arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)]PdBr}

Conditions for the coupling of bromoarenes with esters using a single base and catalyst with improved turnover numbers are described. These general conditions were made possible by using the Pd(l) catalyst {[P(f-Bu) 3]PdBr}2. Reactions of acetates, propionates, and isobutyrates are presented, and reactions of all three classes of esters on a 10 g scale are described.

Palladium-catalyzed-arylattion of esters With chloroarenes

Palladium-catalyzed α-arylations of esters with chloroarenes are reported. The reactions of chloroarenes with the sodium enolates of tert-butyl propionate and methyl isobutyrate occur in high yields with 0.2-1 mol % of {[P(f-Bu)3]PdBr}2/s

Palladium-Catalyzed Arylation of Trimethylsilyl Enolates of Esters and Imides. High Functional Group Tolerance and Stereoselective Synthesis of α-Aryl Carboxylic Acid Derivatives

A general procedure for the palladium-catalyzed arylation of trimethylsilyl enolates of esters and imides is reported. In the presence of ZnF2 or Zn(O-t-Bu)2 as an additive, the trimethylsilyl enolates of esters, including those bearing α-alkoxy derivatives, underwent arylation in high yield with high functional group tolerance. This arylation chemistry was extended to ester derivatives bearing chiral auxiliaries to form new tertiary stereocenters. The arylation of imides bearing the Evans auxiliary proceeded with selectivities up to 90% de. Further, the arylation of the ketal developed by Ley provided α-aryl glycolates with excellent diastereoselectivities (90 to >98% de). This reaction provides a convenient route to the synthesis of enantiopure α-aryl-α-hydroxy esters. Reactions conducted with Zn(O-t-Bu)2 as an additive occurred at room temperature to give enhanced diastereoselectivities with both chiral reagents. Mechanistic studies showed that the reaction conditions are neutral enough that the observed diastereomeric ratios reflect kinetic selectivities.