1835-04-7

Usage

Uses

Used in Organic Synthesis:
1-(3,4-DIMETHOXY-PHENYL)-PROPAN-1-ONE is used as a synthetic intermediate for the production of various organic compounds. Its presence of methoxy groups on the phenyl ring and the propiophenone structure make it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(3,4-DIMETHOXY-PHENYL)-PROPAN-1-ONE is used as a key intermediate in the synthesis of drugs with potential therapeutic applications. Its unique structure allows for the development of new drug candidates with improved pharmacological properties.
Used in Agrochemical Industry:
1-(3,4-DIMETHOXY-PHENYL)-PROPAN-1-ONE is also utilized in the agrochemical industry for the synthesis of active ingredients in pesticides and herbicides. Its chemical properties enable the creation of novel compounds with enhanced efficacy and selectivity in controlling pests and weeds.
Used in Specialty Chemicals:
In the specialty chemicals sector, 1-(3,4-DIMETHOXY-PHENYL)-PROPAN-1-ONE is employed as a precursor for the synthesis of various compounds with specific applications, such as dyes, fragrances, and functional materials. Its versatility in organic synthesis contributes to the development of innovative products with unique properties.

Preparation

Preparation by reaction of dimethyl sulfate with propionylcatechol in alkaline solution (43%).

InChI:InChI=1/C11H14O3/c1-4-9(12)8-5-6-10(13-2)11(7-8)14-3/h5-7H,4H2,1-3H3

Upstream product

• 1568-01-0 3-(N,N-dimethylamino)-1-(3,4-dimethoxyphenyl)propan-1-one 
• 91-16-7 1,2-dimethoxybenzene 
• 79-03-8 propionyl chloride 
• 802294-64-0 propionic acid 
• 123-62-6 propionic acid anhydride 
• 7451-98-1 3',4'-dihydroxypropiophenone 
• 77-78-1 dimethyl sulfate 
• 10548-83-1 1-(3,4-dimethoxyphenyl)propan-1-ol 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 119-64-2 tetralin 
• 5888-52-8 4-propyl-1,2-dimethoxybenzene 
• 121-33-5 vanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 108845-25-6 (E)-4-(but-2-en-2-yl)-1,2-dimethoxybenzene 
• 103502-07-4 1-(3,4-dimethoxy-phenyl)-propane-1,2-dione-2-oxime 
• 4440-92-0 1,4-bis(3,4-dimethoxyphenyl),2,3-dimethylbutane-1,4-dione 
• 4302-34-5 β-Chlor-α-methyl-3,4-dimethoxy-zimtaldehyd 
• 111222-50-5 N-1-(3,4-dimethoxyphenyl)propylformamide 
• 17418-07-4 1,2-dimethoxy-3,4,5-trinitrobenzene 
• 1042551-31-4 [1-(3,4-dimethoxy-phenyl)-propylamino]-acetic acid methyl ester 
• 98876-49-4 5,6-dimethoxy-2-(3,4-dimethoxyphenyl)-3-ethyl-1-methyl-1H-indene 
• 98876-55-2 5,6-diacetoxy-2-(3,4-diacetoxyphenyl)-3-ethyl-1-methyl-3H-indene 
• 126065-87-0 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene 
• 4676-33-9 3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)furan 
• 116588-89-7 3,6-Bis-(3,4-dimethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-pyridazine 
• 116588-90-0 3,6-Bis-(3,4-dimethoxy-phenyl)-1,4,5-trimethyl-1,4-dihydro-pyridazine 
• 116588-91-1 3,6-Bis-(3,4-dimethoxy-phenyl)-4,5-dimethyl-1-phenyl-1,4-dihydro-pyridazine 

Relevant academic research and scientific papers

Friedel-Crafts propionylation of veratrole to 3,4-dimethoxypropiophenone over superacidic UDCaT-5 catalyst

3,4-Dimethoxypropiophenone (3,4-DMPP) is of considerable commercial importance due to its use in fine chemical and drug industries. 3,4-DMPP is traditionally produced by the Friedel-Crafts propionylation of veratrole using homogeneous catalysts which are

Preparation method and application of apocynin and derivatives of apocynin

The invention belongs to the technical field of chemical biology, and particularly relates to a preparation method of apocynin and derivatives of the apocynin and an application of the apocynin and the derivatives of the apocynin in skin care products. The apocynin and the derivatives of the apocynin provided by the invention can promote collagen synthesis, help skin damage repair, and can be usedin the skin care products.

Cobalt-Catalyzed Migrational Isomerization of Styrenes

An efficient cobalt-catalyzed migrational isomerization of styrenes was developed using the thiazoline iminopyridine (TIP) ligand. This reaction is operationally simple and atom-economical using readily available starting materials to access trisubstituted alkenes. Even when using a 0.1 mol % catalyst loading, the reaction could be conducted in neat and completed in 1 h with excellent conversion and high E stereoselectivity.

Cleavage of CC and Co bonds in β-O-4 linkage of lignin model compound by cyclopentadienone group 8 and 9 metal complexes

Degradation of 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphe-noxy)propane-1,3-diol (1), a model compound for lignin β-O-4 linkage was examined with iron, ruthenium, rhodium and iridium complexes bearing cyclopentadienone ligand. Cyclopentadienone iron complex gave only a small amount of degraded product with reduced molecular weight. Cyclopentadienone ruthenium complex, so called Shvo's catalyst, afforded 3,4-dimethoxybenzaldehyde (a3) in 14.3% yield after CαCβ bond cleavage. On the other hand, cyclopentadienone group-9 metal complexes catalyzed CβO bond cleavage to afford guaiacol (b1) as a main product in up to 74.9% yield.

Rhodium-terpyridine catalyzed redox-neutral depolymerization of lignin in water

Simple rhodium terpyridine complexes were found to be suitable catalysts for the redox neutral cleavage of lignin in water. Apart from cleaving lignin model compounds into ketones and phenols, the catalytic system could also be applied to depolymerize dioxasolv lignin and lignocellulose, affording aromatic ketones as the major monomer products. The (hemi)cellulose components in the lignocellulose sample remain almost intact during lignin depolymerization, providing an example of a "lignin-first" process under mild conditions. Mechanistic studies suggest that the reaction proceeds via a rhodium catalyzed hydrogen autotransfer process.

METHOD FOR THE DEACYLATION AND/OR DEALKYLATION OF COMPOUNDS

The present invention in general relates to a method for the deacylation and/or dealkylation (both O-dealkylation as well as C-dealkylation) of compounds, more specifically of aromatic compounds. The method is characterized by contacting the compound with an acid-containing aqueous reaction mixture using high temperature and high pressure conditions. The invention also provides a method for preparing a compound suitable for further deacylation using the method of the invention.

A convenient synthetic approach to dioncoquinone B and related compounds

A total synthesis of dioncoquinone B and related compounds, including ancistroquinones B, C and malvon A, is presented. The strategy is based on available reagents and can be used as a preparative synthesis of a number of natural and synthetic biologically active (3-alkyl)-2,7,8-di(tri)methoxy(hydroxy)-1,4-naphthoquinones.

Mild Redox-Neutral Depolymerization of Lignin with a Binuclear Rh Complex in Water

A mild redox-neutral lignin depolymerization system featuring a water-soluble binuclear Rh complex has been developed. The catalytic system could be successfully applied to the depolymerization of a lignin-like polymer, alkaline lignin, as well as raw lignocellulose samples to produce aromatic ketones, providing a homogeneous catalytic system for "lignin-first" biorefinery in water. Mechanistic studies on the model substrate suggest that the reaction proceeds via a metal-catalyzed dehydrogenation step to afford a carbonyl intermediate, followed by C-O bond cleavage to afford ketone and phenol products. Deuterium labeling study shows that the hydrogen used for cleavage of the C-O bond originates from the alcohol moiety in the substrate.

Promoting Lignin Depolymerization and Restraining the Condensation via an Oxidation-Hydrogenation Strategy

For lignin valorization, simultaneously achieving the efficient cleavage of ether bonds and restraining the condensation of the formed fragments represents a challenge thus far. Herein, we report a two-step oxidation-hydrogenation strategy to achieve this goal. In the oxidation step, the O2/NaNO2/DDQ/NHPI system selectively oxidizes CαH-OH to Cα=O within the β-O-4 structure. In the subsequent hydrogenation step, the α-O-4 and the preoxidized β-O-4 structures are further hydrogenated over a NiMo sulfide catalyst, leading to the cleavage of Cβ-OPh and Cα-OPh bonds. Besides the transformation of lignin model compounds, the yield of phenolic monomers from birch wood is up to 32% by using this two-step strategy. The preoxidation of CαH-OH to Cα=O not only weakens the Cβ-OPh ether bond but also avoids the condensation reactions caused by the presence of Cα+ from dehydroxylation of CαH-OH. Furthermore, the NiMo sulfide prefers to catalyze the hydrogenative cleavage of the Cβ-OPh bond connecting with a Cα=O rather than catalyze the hydrogenation of Cα=O back to the original CαH-OH, which further ensures and utilizes the advantages of preoxidation.

Visible-Light-Driven Self-Hydrogen Transfer Hydrogenolysis of Lignin Models and Extracts into Phenolic Products

Obtaining high selectivity of aromatic monomers from renewable lignin has been extensively pursued but is still unsuccessful, hampered by the need to efficiently cleave C-O/C-C bonds and inhibit lignin proliferation reactions. Herein, we report a transfer hydrogenolysis protocol using a heterogeneous ZnIn2S4 catalyst driven by visible light. In this process, alcoholic groups (CαH-OH) of lignin act as hydrogen donors. Proliferation of phenolic products to dark substances is suppressed under visible light illumination at low temperature (below 50 °C); formation of a light and transparent reaction solution allows visible light to be absorbed by the catalyst. With this strategy, 71-91% yields of phenols in the conversion of lignin β-O-4 models and a 10% yield of p-hydroxyl acetophenone derivatives from organosolv lignin are achieved. Mechanistic studies reveal that CαH-OH groups of lignin β-O-4 linkage are initially dehydrogenated on ZnIn2S4 to form a "hydrogen pool", and the adjacent Cβ-O bond is subsequently hydrogenolytically cleaved to two monomers by the "hydrogen pool". Thus, the dehydrogenation and hydrogenolysis reaction are integrated in one-pot with lignin itself as a hydrogen donor. This study shows a promising way of supplying phenolic compounds by taking advantages of both renewable biomass feedstocks and photoenergy.