1136-86-3

Usage

Uses

Used in Agrochemical Industry:
3',4',5'-Trimethoxyacetophenone is used as an intermediate in the synthesis of agrochemicals for enhancing crop protection and yield. Its unique chemical structure contributes to the development of effective and targeted agrochemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 3',4',5'-Trimethoxyacetophenone serves as a key intermediate in the production of various drugs. Its chemical properties allow for the creation of novel compounds with potential therapeutic applications.
Used in Dyestuff Industry:
3',4',5'-Trimethoxyacetophenone is utilized as a building block for the synthesis of dyes and pigments, particularly those with specific color properties. Its incorporation into dyestuff formulations enables the development of a wide range of colors and hues for various applications.

Preparation

Obtained by treatment of a mixture of methyl 3,4,5-trimethoxybenzoate (m.p. 82°) and ethyl acetate with sodium on a water boiler for 8 h, then with 25% sulfuric acid.

Upstream product

• 186581-53-3 diazomethane 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 917-54-4 methyllithium 
• 118-41-2 Eudesmic acid 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 1885-35-4 3,4,5-trimethoxybenzonitrile 
• 36266-40-7 1-(3,4,5-trimethoxyhenyl)ethanol 
• 858468-00-5 1,2,3-trimethoxy-5-(prop-1-en-2-yl)benzene 
• 10028-15-6 ozone 
• 64-19-7 acetic acid 
• 266329-28-6 1-(dimethylphenylsilyl)-1-(3,4,5-trimethoxyphenyl)ethanol 
• 3086-62-2 3,4,5-trimethoxybenzamide 

Downstream Products

• 1041-10-7 3-(piperidin-1-yl)-1-(3,4,5-trimethoxyphenyl)propan-1-one hydrochloride 
• 58344-62-0 (E)-3-(3,4-methylenedioxyphenyl)-1-(3,4,5-trimethoxy-phenyl)-prop-2-en-1-one 
• 130768-87-5 (2E)-1-(3',4',5'-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one 
• 127033-98-1 (E)-3-phenyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 110048-17-4 3',4,4',5'-tetramethoxychalcone 
• 111797-23-0 (E)-3-(3,4-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one 
• 70909-47-6 ethyl 2,4-dioxo-4-(3,4,5-trimethoxyphenyl)butanoate 
• 3044-56-2 ethyl trimethoxybenzoyl acetate 
• 101256-79-5 3-morpholin-4-yl-1-(3,4,5-trimethoxy-phenyl)-propan-1-one 
• 3704-91-4 1-[4-(2-Diethylamino-ethoxy)-phenyl]-1-(3,4,5-trimethoxy-phenyl)-ethylen 
• 64039-00-5 1-morpholino-2-(3,4,5-trimethoxyphenyl)ethanethione 
• 127034-10-0 (E)-3-(4-trifluoromethylphenyl)-1-(3,4,5-trimethoxyphenyl)-3-phenylprop-2-en-1-one 
• 139515-39-2 N-(4,5-Diphenyl-oxazol-2-yl)-N'-[1-(3,4,5-trimethoxy-phenyl)-eth-(E)-ylidene]-hydrazine 
• 127034-04-2 (E)-3-(4-Amino-phenyl)-1-(3,4,5-trimethoxy-phenyl)-propenone 

Relevant academic research and scientific papers

Synthesis and biological evaluations of 1,2-diaryl pyrroles as analogues of combretastatin A-4

A series of novel 1,2-diaryl pyrroles as analogues of combretastatin A-4 (CA-4, 1a) were synthesized and evaluated for their antitumour potential against three cancer cell lines. Most compounds exhibited growth inhibition against all of the cancer cell lines. Compound 7q not only exhibited prominent antitumour efficacy with IC50 values of 0.390 μm in SGC-7901, 0.070 μm in HT-1080 and 0.045 μm in KB cell lines but also showed low activity with IC50 values of 30.08 μm in normal L929 cell line. Moreover, compound 7q inhibited tubulin polymerization into microtubules and caused microtubule destabilization. A molecular docking study of 7q was performed to determine its binding mode at the colchicine site in the tubulin dimer. 1,2-Diaryl pyrroles as combretastatin A-4 analogues were synthesized and evaluated for anti-proliferative activities. Compound 7q exhibited antitubulin activity.

Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties

5-Aminoisoxazoles containing trimethoxy- and methylenedioxyphenyl moieties were prepared by heterocyclization of electrophilic alkenes with tetranitromethane in the presence of triethylamine with subsequent reduction of resulting 5-nitroisoxazoles. The cr

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

Electro-reductive Fragmentation of Oxidized Lignin Models

Lignin provides a potential sustainable source for production of electron-rich aromatic compounds. Recently, electrochemical lignin degradation via an oxidation/reduction sequence under mild conditions has garnered much attention within the lignin community, as electrochemistry simplifies redox reactions and offers an electron source/sink for synthesis without using stoichiometric oxidants or reductants. This paper describes a fundamental approach for the electrochemical fragmentation of the primary connection in native lignin, β-O-4. Potential-controlled electrolysis enables selective reduction and provides fragmentation products and/or coupling products in isolated yields of 59-92%.

Sequential Cleavage of Lignin Systems by Nitrogen Monoxide and Hydrazine

The cleavage of representative lignin systems has been achieved in a metal-free two-step sequence first employing nitrogen monoxide for oxidation followed by hydrazine for reductive C?O bond scission. In combining nitrogen monoxide and lignin, the newly developed valorization strategy shows the particular feature of starting from two waste materials, and it further exploits the attractive conditions of a Wolff-Kishner reduction for C?O bond cleavage for the first time. (Figure presented.).

Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN

A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also shown that nitrogenated substrates such as hydrazones, N-tosylhydrazones, and ketimines reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.

Aerobic oxidation of alcohols with air catalyzed by decacarbonyldimanganese

The oxidation of alcohols to carbonyl compounds using air as the terminal oxidant is highly desirable. As described in previous reports, the abstraction of α-H of the alcohol is the most important step, and it typically requires not only a metal catalyst but also complex ligands, co-catalysts and bases. Herein, we report a practical and efficient method for the oxidation of primary alcohols, secondary alcohols, 1,2-diols, 1,2-amino alcohols, and other α-functionalized alcohols using a commercially available catalyst, Mn2(CO)10, and no additives. Preliminary mechanistic studies indicated that an alkoxyl radical intermediate existed in our system, and a plausible mechanism consistent with the experimental results and literature was proposed.

Visible light induced redox neutral fragmentation of 1,2-diol derivatives

A homogeneous, redox-neutral photo fragmentation of diol derivatives was developed. Under photo/hydrogen atom transfer (HAT) dual catalysis, diol derivatives such as lignin model compounds and diol monoesters undergo selective β C(sp3)-O bond cleavage to afford ketones, phenols and acids effectively.

Fine Tuning the Redox Potentials of Carbazolic Porous Organic Frameworks for Visible-Light Photoredox Catalytic Degradation of Lignin β-O-4 Models

We report a facile approach to fine tune the redox potentials of π-conjugated porous organic frameworks (POFs) by copolymerizing carbazolic electron donor (D) and electron acceptor (A) based comonomers at different ratios. The resulting carbazolic copolymers (CzCPs) exhibit a wide range of redox potentials that are comparable to common transition-metal complexes and are used in the stepwise photocatalytic degradation of lignin β-O-4 models. With the strongest oxidative capability, CzCP100 (D:A = 0:100) exhibits the highest efficiency for the oxidation of benzylic β-O-4 alcohols, while the highly reductive CzCP33 (D:A = 66:33) gives the highest yield for the reductive cleavage of β-O-4 ketones. CzCPs also exhibit excellent stability and recyclability and represent a class of promising heterogeneous photocatalysts for the production of fine chemicals from sustainable lignocellulosic biomass.

Synthesis and biological evaluation of 3-alkyl-1,5-diaryl-1H-pyrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative activity

A series of novel 3-alkyl-1,5-diaryl-1H-pyrazoles were synthesized as combretastatin A-4 (CA-4) analogues and evaluated for antiproliferative activity against three human cancer cell lines (SGC-7901, A549 and HT-1080). Most of the target compounds displayed moderate to potent antiproliferative activity, and 7k was found to be the most potent compound. Structure-activity relationships indicated that compounds with a trimethoxyphenyl A-ring at the N-1 position of the pyrazole skeleton were more potent than those with the A-ring at the C-5 position. Tubulin polymerization and immunostaining experiments revealed that 7k potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Computational modelling demonstrated that the binding of 7k to the colchicine binding site on microtubules may involve a similar mode as CA-4.