1201-38-3

Usage

Uses

Used in Pharmaceutical Industry:
2',5'-Dimethoxyacetophenone is used as a key intermediate for the preparation of pyridine and thieno[2,3-b]pyridine derivatives, which are known as anticancer PIM-1 kinase inhibitors. These inhibitors play a crucial role in the development of targeted cancer therapies, as they help in modulating the activity of specific enzymes involved in cancer cell growth and survival.
Additionally, 2',5'-Dimethoxyacetophenone is utilized in the synthesis of anti-cancer and apoptosis-inducing agents. These agents are designed to trigger programmed cell death (apoptosis) in cancer cells, thereby contributing to the development of novel cancer treatment strategies.

Preparation

Obtained by reaction of dimethyl sulfate with quinacetophenone in the presence of 10% aqueous sodium hydroxide.

Upstream product

• 108-24-7 acetic anhydride 
• 150-78-7 1,4-dimethoxybezene 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 77-78-1 dimethyl sulfate 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 67-56-1 methanol 
• 1204-21-3 2-bromo-2',5'-dimethoxyacetophenone 
• 41038-40-8 1-(2,5-bis(methoxy)phenyl)ethan-1-ol 
• 75-05-8 acetonitrile 
• 176226-18-9 2,3-bis-(2,5-dimethoxy-phenyl)-butane-2,3-diol 
• 208937-71-7 [1-(2,5-Dimethoxy-phenyl)-vinyloxy]-diphenyl-silane 
• 127-17-3 2-oxo-propionic acid 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 58344-61-9 (E)-1-(2,5-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)-prop-2- en-1-one 
• 6665-83-4 6-hydroxyflavone 
• 109469-64-9 2-hydroxy-3,2',5'-trimethoxy-trans-chalcone 
• 110048-16-3 2,3,2',5'-tetramethoxy-trans-chalcone 
• 107828-85-3 (E)-1-(2,5-dimethoxyphenyl)ethylidene(isopropylidene)succinic anhydride 
• 107828-79-5 (Z)-1-(2,5-dimethoxyphenyl)ethylidene(isopropylidene)succinic anhydride 
• 72229-44-8 2',5'-dimethoxyacetophenone dimethyl acetal 
• 81008-14-2 4-(2,5-dimethoxyphenyl)-4-oxo-2-hydroxy-butanoic acid 
• 158919-81-4 1,3-bis(2,5-dimethoxyphenyl)-2-propen-1-one 
• 18113-18-3 2,5-dimethoxyphenol 
• 89556-66-1 (Z)-1,4-dimethoxy-2-(1-methyl-1-propenyl)benzene 
• 208937-71-7 [1-(2,5-Dimethoxy-phenyl)-vinyloxy]-diphenyl-silane 
• 221194-99-6 1-(2,5-dimethoxyphenyl)-3-hydroxy-9-phenylnonan-1-one 

Relevant academic research and scientific papers

Solid supported Ru(0) nanoparticles: An efficient ligand-free heterogeneous catalyst for aerobic oxidation of benzylic and allylic alcohol to carbonyl

Polymer immobilized stable, spherical ruthenium nanoparticles were prepared, characterized, and acted as a heterogeneous catalyst for the selective benzylic and allylic alcohol oxidation into the corresponding carbonyls using molecular oxygen. The solid supported Ru(0) (SS-Ru) as a heterogeneous catalyst exhibits good reusability and easy separation from the reaction mixture by filtration.

Design, synthesis and docking study of pyridine and thieno[2,3-b] pyridine derivatives as anticancer PIM-1 kinase inhibitors

A series of pyridine and thieno[2,3-b]pyridine derivatives have been designed and synthesized as anticancer PIM-1 kinase inhibitors. Thirty-seven compounds were selected by NCI to be tested initially at a single dose (10 μM) in the full NCI 60 cell line panel. Compound 5b showed potent anticancer activity and was tested twice in the five-dose assay which confirmed its potent antitumor activity (GI50 values 0.302–3.57 μM) against all tested tumor cell lines except six cell lines where they showed moderate sensitivity. This compound was sent to NCI biological evaluation committee and still under consideration for further testing. In addition, the most active anticancer compounds in each series, 5b, 8d, 10c, 13h, and 15e, were evaluated for their PIM-1 kinase inhibitory activity. Compound 8d was the most potent one with IC50 = 0.019 μM followed by 5b, 15e, 10c and 13h with IC50 values 0.044, 0.083, 0.128 and 0.479 μM respectively. Moreover, docking study of the most active compounds in PIM-1 kinase active site was consistent with the in vitro activity.

Solid-supported Pd(0): An efficient heterogeneous catalyst for aerobic oxidation of benzyl alcohols into aldehydes and ketones

Solid-supported nano- and microparticles of Pd(0) (SS-Pd) were used as heterogeneous catalysts for aerobic oxidation of benzyl alcohols. Primary and secondary benzyl alcohols gave the corresponding products in good yields. In addition, the catalysts could be reused up to five runs without significant loss of activities.

Phytochemistry of Genus Gentiana. XXVI. Identification of a New Di-O-glucosyl Cinnamoyl-C-glucosylflavone in the Leaves of Gentiana X marcailhouana RY.

A new di-O-glucosyl cinnamoyl-C-glucosylflavone has been identified as 4'-O-β-D-glucosyl-2''-O-isoorientin (1).

Preparation method of 2, 5-dimethoxyphenylacetic acid

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 2, 5-dimethoxyphenylacetic acid, which comprises the following steps: A. Reacting 1,4-dimethoxybenzene with formaldehyde under the action of hydrogen halide, extracting by the reaction system, merging with organic phases, drying, concentrating under reduced pressure, and purifying the crude product to obtain 2-halon methyl-1, 4-dimethoxybenzene ; and B, under the protection of inert gas, putting the 2-halo methyl-1, 4-dimethoxybenzene obtained in the step A, magnesium or butyl lithium and carbon dioxide into a solvent, and then carrying out extraction and deactivation, reduced pressure distillation, extraction, organic phase combination and reduced pressure concentration toobtain the 2, 5-dimethoxyphenylacetic acid. The yield and the total yield of the 2, 5-dimethoxyphenylacetic acid obtained by the method disclosed by the invention are both higher than those of the 2,5-dimethoxyphenylacetic acid synthesized by a Willgerodt-Kindler method.

Preparation method of 2,5-dimethoxyphenylacetic acid

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 2,5-dimethoxyphenylacetic acid, wherein the preparation method comprises the following steps: A, reacting 1,4-dimethoxybenzene with formaldehyde under the action of hydrogen halide to obtain 2-halomethyl-1,4-dimethoxybenzene; B, reacting 2-halomethyl-1,4-dimethoxybenzene obtained inthe step A with a cyanation reagent, then diluting, washing, drying and concentrating under reduced pressure, and finally carrying out reduced pressure distillation to obtain 2(2,5-dimethoxyphenyl)acetonitrile; and C, hydrolyzing the 2(2,5-dimethoxyphenyl)acetonitrile obtained in the step B, cooling, extracting, merging, drying, concentrating under reduced pressure and purifying to finally obtainthe 2,5-dimethoxyphenylacetic acid. The yield and the total yield of the 2,5-dimethoxyphenylacetic acid obtained by the method disclosed by the invention are both higher than those of the 2,5-dimethoxyphenylacetic acid synthesized by a Willgerodt-Kindler method, and the yield and the total yield of the 2,5-dimethoxyphenylacetic acid are higher than those of 2,5-dimethoxyphenylacetic acid synthesized by the Willgerodt-Kindler method.

Preparation method of 2,5-dimethoxyphenylacetic acid

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 2,5-dimethoxyphenylacetic acid, wherein the method comprises the following steps: A,reacting 1,4-dimethoxybenzene in a formylation system to obtain 2,5-dimethoxybenzaldehyde; B, reacting the 2,5-dimethoxybenzaldehyde obtained in the step A with a reducing agent, extracting a reaction system, then combining organic phases, drying, concentrating under reduced pressure and distilling a crude product to obtain 2,5-dimethoxybenzyl alcohol; C, reacting the 2,5-dimethoxybenzyl alcoholobtained in the step B with a bromination reagent to obtain 2-bromomethyl-1,4-dimethoxybenzene; and D, reacting the 2-bromomethyl-1,4-dimethoxybenzene obtained in the step C with magnesium or butyl lithium and carbon dioxide in a solvent to obtain the 2,5-dimethoxyphenylacetic acid. The yield and the total yield of the 2,5-dimethoxyphenylacetic acid obtained by the method disclosed by the invention are both higher than those of 2,5-dimethoxyphenylacetic acid synthesized by a Willegerdt-Kindler method.

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.

Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones

A mimic of the Wacker process for C=O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.

Synthesis of industrially important aromatic and heterocyclic ketones using hierarchical ZSM-5 and Beta zeolites

Hierarchical ZSM-5 and Beta zeolites were investigated in the synthesis of wide range of industrially important aromatic/heterocyclic ketones by Friedel-Crafts acylation and benzoylation reactions. For comparative study, conventional ZSM-5 and Beta, and amorphous mesoporous Al-MCM-41 were investigated. Hierarchical zeolites were prepared by multi-ammonium structure directing agents whereas conventional zeolites were prepared by mono-ammonium structure directing agents. Among the catalysts investigated in this study, hierarchical Beta exhibited the highest reactant conversion in the acylation and benzoylation reactions. In this study, the systematic assessment of the catalytic activity of acid catalysts for wide range of aromatic and heterocyclic compounds is shown under one umbrella. To the best of our knowledge, these reactions over hierarchical zeolites (ZSM-5 and Beta) are reported here for the first time. Structure activity relationship is explained based on the physico-chemical properties, molecular size, reactivity of reactants, and reaction mechanism. Catalysts can be easily recovered and reused with negligible loss in the catalytic activity.