579-74-8

Usage

Uses

Used in Pharmaceutical Industry:
2'-Methoxyacetophenone is used as a building block for the preparation of chalcones, specifically the chalcones of 3-benzylidene-2-chlorocyclohex-1-enecarbaldehyde. These chalcones have potential applications as anti-proliferative agents, which can be beneficial in the development of new drugs and therapies for various medical conditions.
Used in Flavor and Fragrance Industry:
Due to its unique anisic almond aroma, 2'-Methoxyacetophenone can be utilized as a component in the creation of various flavors and fragrances. Its medium strength odor makes it suitable for use in the formulation of different scent profiles, enhancing the sensory experience of various products.
Used in Chemical Research:
As an organic compound with distinct chemical properties, 2'-Methoxyacetophenone can also be employed in chemical research and development. It can serve as a starting material or intermediate in the synthesis of more complex molecules, contributing to the advancement of chemical science and technology.

Preparation

Preparation by reaction of dimethyl sulfate with o-hydroxyacetophenone in the presence of sodium hydroxide.

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 2605, 1981 DOI: 10.1016/S0040-4039(01)90532-5Journal of the American Chemical Society, 72, p. 5161, 1950 DOI: 10.1021/ja01167a100The Journal of Organic Chemistry, 52, p. 150, 1987 DOI: 10.1021/jo00377a027

Upstream product

• 917-64-6 methyl magnesium iodide 
• 6609-56-9 2-methoxy-benzonitrile 
• 10278-02-1 2-(2-methoxyphenyl)propene 
• 41607-95-8 3-(2-methoxy-phenyl)-3-oxo-propionic acid ethyl ester 
• 118-93-4 o-hydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 463-51-4 Ketene 
• 100-66-3 methoxybenzene 
• 506-82-1 dimethylcadmium 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 51674-10-3 N,N-diethyl-2-methoxybenzamide 
• 917-54-4 methyllithium 
• 1878-62-2 2-(2-acetylphenoxy)acetic acid 

Downstream Products

• 6948-61-4 (E)-1-(2-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 7706-84-5 3-(2-methoxy-phenyl)-crotonic acid ethyl ester 
• 133571-96-7 ethyl 3-hydroxy-3-(2-methoxyphenyl)butanoate 
• 854-14-8 1-(2-methoxy-phenyl)-ethanone-(2,4-dinitro-phenylhydrazone) 
• 17572-29-1 2-<1-Methylpenten-(1)-yl>-anisol 
• 802005-82-9 2-(2-methoxy-phenyl)-2-methyl-thiazolidine 
• 17403-73-5 2-<1-Methylocten-(1)-yl>-anisol 
• 17475-07-9 2-<1-Methyl-hexen-(1)-yl>-anisol 
• 24892-80-6 2-(1-phenylvinyl)anisole 
• 23045-68-3 5-[1-(2-methoxy-phenyl)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 77664-74-5 2,4-dioxo-4-(2-methoxyphenyl)butanoic acid 
• 60943-26-2 3-[2-(2-Methoxy-phenyl)-2-oxo-ethyl]-1H-quinoxalin-2-one 
• 128588-62-5 5-(2-methoxyphenyl)-2,3-diphenyl-1H-pyrrole 
• 29242-34-0 2-Hydroxy-4-(2-methoxy-phenyl)-2-methyl-4-oxo-butyric acid 

Relevant academic research and scientific papers

-OH-Induced shift from carbon to oxygen acidity in the side-chain deprotonation of 2-, 3- and 4-methoxybenzyl alcohol radical cations in aqueous solution: Results from pulse radiolysis and DFT calculations

DFT calculations have been carried out for 2-, 3- and 4-methoxybenzyl alcohol radical cations (1·+, 3·+ and 4·+, respectively) and the α-methyl derivatives 2·+ and 5·+ using the UB3LYP/6-31G(d) method. The theoretical results have been compared with the experimental rate constants for deprotonation of 1·+-5·+ under acidic and basic conditions. In acidic solution, the decay of 1·+-5·+ proceeds by cleavage of the C-H bond, while in the presence of -OH all the radical cations undergo deprotonation from the α-OH group. This pH-dependent change in mechanism has been interpreted qualitatively in terms of simple frontier molecular orbital theory. The -OH induced α-O-H deprotonation is consistent with a charge controlled reaction, whereas the C-H deprotonation, observed when the base is H2O, appears to be affected by frontier orbital interactions.

Discovery of Chromane-6-Sulfonamide Derivative as a Potent, Selective, and Orally Available Novel Retinoic Acid Receptor-Related Orphan Receptor γt Inverse Agonist

Interleukin-17 (IL-17) is a proinflammatory cytokine that plays a dominant role in inflammation, autoimmunity, and host defense. RORγt is a key transcription factor mediating T helper 17 (Th17) cell differentiation and IL-17 production, which is able to activate CD8+ T cells and elicit antitumor efficacy. A series of sulfonamide derivatives as novel RORγt inverse agonists were designed and synthesized. Using GSK2981278 (phase II) as a starting point, we engineered structural modifications that significantly improved the activity and pharmacokinetic profile. In animal studies, oral administration of compound d3 showed a robust and dose-dependent inhibition of the IL-17A cytokine expression in a mouse imiquimod-induced skin inflammation model. Docking analysis of the binding mode revealed that the compound d3 occupied the active pocket suitably. Thus, compound d3 was selected as a clinical compound for the treatment of Th17-driven autoimmune diseases.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Visible-Light-Driven Selective Air-Oxygenation of C?H Bond via CeCl3 Catalysis in Water

Visible-light-induced C?H aerobic oxidation is an important chemical transformation that can be applied for the synthesis of aromatic ketones. High-cost catalysts and toxic solvents were generally needed in the present methodologies. Here, an efficient aqueous C?H aerobic oxidation protocol was reported. Through CeCl3-mediated photocatalysis, a series of aromatic ketones were produced in moderate to excellent yields. With air as the oxidant, this reaction could be performed under mild conditions in water and demonstrated high activity and functional group tolerance. This method is economical, highly efficient, and environmentally friendly, and it will provide inspiration for the development of aqueous photochemical synthesis reactions.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

The dehydrogenative oxidation of aryl methanols using an oxygen bridged [Cu-O-Se] bimetallic catalyst

Herein, we report a new protocol for the dehydrogenative oxidation of aryl methanols using the cheap and commercially available catalyst CuSeO3·2H2O. Oxygen-bridged [Cu-O-Se] bimetallic catalysts are not only less expensive than other catalysts used for the dehydrogenative oxidation of aryl alcohols, but they are also effective under mild conditions and at low concentrations. The title reaction proceeds with a variety of aromatic and heteroaromatic methanol examples, obtaining the corresponding carbonyls in high yields. This is the first example using an oxygen-bridged copper-based bimetallic catalyst [Cu-O-Se] for dehydrogenative benzylic oxidation. Computational DFT studies reveal simultaneous H-transfer and Cu-O bond breaking, with a transition-state barrier height of 29.3 kcal mol?1

Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride

Selective oxidation of C(sp3)-H bonds to carbonyl groups by abstracting H with a photoinduced highly active oxygen radical is an effective method used to give high value products. Here, we report a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ= 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride. The optimized cation (C) of Fe3+or Ni2+, with an anion (A) of phosphotungstate (PW123?) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12dual-metal-site as a model (FePW), we demonstrate a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples). The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4that is mediated by thetBuO˙ andtBuOO˙ radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature. In addition, this A-C/g-C3N4photocatalyst is highly robust and can be reused at least six times and the activity is maintained.

Preparation of trinuclear ruthenium clusters based on piconol ligands and their application in Oppenauer-type oxidation of secondary alcohols

Treatment of Ru3(CO)12 with one equivalent of 2-indolyl-6-pyridinyl-alcohol ligands 2-(C8H6N)-6-(CR1R2OH)C5H3N (R1 = R2 = Me (L1H); R1 = R2 = C2H5 (L2H); R1, R2 = ?(CH2)4- (L3H);& R1, R2 = ?(CH2)5- (L4H)) in refluxing THF afforded the corresponding trinuclear ruthenium clusters L(μ2-H)Ru3(CO)9 (1a–1d), respectively. All the novel Ru complexes were well characterized by NMR, elemental analyses and IR spectra. Structures of complexes 1a, 1c, and 1d were further determined by X-ray crystallographic studies. Complexes 1a–1d were applied to catalytic Oppenauer-type oxidation of secondary alcohols with acetone as oxidant, and complex 1a was found to be the most efficient catalyst.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.