64591-47-5

Upstream product

• 1738-36-9 2-methoxyacetonitrile 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 67-56-1 methanol 
• 54731-27-0 1-p-methylphenyl-1-trimethylsiloxyethene 
• 122-00-9 para-methylacetophenone 
• 104-87-0 4-methyl-benzaldehyde 
• 71878-80-3 1-(methoxymethyl)-1H-benzotriazole 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 104-85-8 para-methylbenzonitrile 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 124-41-4 sodium methylate 
• 619-41-0 4-(bromoacetyl)toluene 
• 122334-36-5 N-methoxy-N,4-dimethylbenzamide 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 108368-38-3 5-methoxy-4-phenyl-6-p-tolyl-pyran-2-one 
• 33524-71-9 3,4-diphenyl-6-(p-tolyl)-2H-pyran-2-one 
• 111354-89-3 (+/-)-4-methoxy-5-oxo-3-phenyl-5-p-tolyl-pent-2c-enoic acid 
• 102174-12-9 1-amino-5-methoxy-4-phenyl-6-p-tolyl-1H-pyridin-2-one 
• 109811-62-3 5-methoxy-4-phenyl-6-p-tolyl-pyridin-2-ol 
• 111441-66-8 5-methoxy-4-phenyl-6-p-tolyl-pyran-2-thione 

Relevant academic research and scientific papers

Intermolecular C-O Bond Formation with Alkoxyl Radicals: Photoredox-Catalyzed α-Alkoxylation of Carbonyl Compounds

Due to the high reactivity of alkoxyl (RO·) radicals and their propensity to easily undergo β-scission or Hydrogen Atom Transfer (HAT) reactions, intermolecular alkoxylations involving RO· radicals are barely described. We report herein for the first time the efficient intermolecular trapping of alkoxyl radicals by silyl enol ethers. This photoredox-mediated protocol enables the introduction of both structurally simple and more complex alkoxy groups into a wide range of ketones and amides.

Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo

A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.

Direct Synthesis of α-Alkoxy Ketones by Oxidative C–O Bond Formation

A convenient method to prepare α-alkoxy ketones has been developed by oxidative coupling of aryl methyl ketones and alcohols. With aqueous tert-butyl hydroperoxide (6.0 equiv.) as the oxidant, tetrabutylammonium iodide (20 mol-%) as the catalyst, and TsNHNH2(1.0 equiv.) as the additive, ketones underwent direct alkoxylation to give α-methoxy or α-ethoxy ketones in moderate to good yields.

Highly efficient synthesis of functionalized α-oxyketones: Via Weinreb amides homologation with α-oxygenated organolithiums

An efficient, chemoselective homologation of Weinreb amides to the corresponding variously substituted α-oxyketones has been developed via the addition of lithiated α-oxygenated species. This one-step, experimentally easy, high yielding protocol is amenable not only for accessing simple α-oxyketones but also for more complex substituted ones ranging from primary and secondary alkyl-type to aromatic ones. Full delivery of the stereochemical information contained in the starting materials is observed through both the employment of enantioenriched Weinreb amides and optically active organolithium species.

Experimental study on the reaction pathway of α-haloacetophenones with NaOMe: Examination of bifurcation mechanism

The reaction of PhCOCH2Br and NaOMe in MeOH gave PhCOCH 2OH as the major product and PhCOCH2OMe as the minor product. Substituent effects on the reactivity and product selectivity revealed that an electron-withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was indicated that the alcohol was formed via carbonyl addition-epoxidation, whereas the ether was formed by direct substitution. Substituent effects on the reaction rates, as well as the effects of NaOMe concentration on the rate and product ratio for both reactions of PhCOCH2Br and PhCOCH2CI are in line with the mechanism that the alcohol and ether products were formed via two independent and concurrent routes, carbonyl addition and a-carbon attack, respectively, and thus the reaction mechanism could be different from the bifurcation mechanism previously predicted for the reaction of PhCOCH2Br by a simulation study in the gas phase.

Oxidative iodination of carbonyl compounds using ammonium iodide and oxone

A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.

Indium triflate: A mild and efficient Lewis acid catalyst for O-H insertion reactions of α-diazo ketones

Facile O-H insertion reactions of α-diazo ketones with aliphatic/aromatic alcohols or benzenethiol have been developed in the presence of indium triflate as a catalyst. These reactions provided good yields of α-alkoxy ketones. A comparative study with other Lewis acids establishes the reactivity of indium triflate in O-H insertion reactions of α-diazo ketones.

Novel cerium(IV) ammonium nitrate mediated transformation of styrenes to α-methoxy acetophenones

Styrenes when treated with a methanolic solution of CAN underwent a novel transformation to α-methoxy acetophenones presumably via a radical cation.

Reaction of phosphonium ylides and aromatic nitriles under lewis acid conditions: An easy access to aryl-substituted α-methoxyacetophenones

In the presence of lithium chloride, as Lewis acid, the reaction of methoxymethyltriphenylphosphonium ylide 1 with aromatic nitriles 2 as phenacyl cation equivalents gives access to the corresponding α- methoxyacetophenones 3 in good yields.

Base-catalyzed rearrangement of α-benzotriazolyl alkoxide anions: Synthesis of one-carbon homologated α-substituted alkyl ketones

Deprotonated benzotriazole derivatives (1a-c) reacted with aldehydes to give the α-oxyanion substituted intermediates (2), which upon further treatment with butyllithium, without separation, resulted in the formation of one-carbon homologated α-substituted alkyl ketones (6a-f). Similar treatment of benzotriazole derivatives (1d-f) generated the benzotriazole ring-opening and rearranged products (7a-f). Plausible mechanisms for these reactions have been proposed.