33731-40-7

Upstream product

• 105174-63-8 3-bromo-1-(3,4-dimethoxyphenyl)propan-1-one 
• 10535-17-8 1-(3,4-dimethoxyphenyl)-2-(methoxyphenoxy)propane-1,3-diol 
• 50-00-0 formaldehyd 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 1416781-21-9 3-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)butane-1,3-diol 
• 4693-38-3 3-chloro-1-(3,4-dimethoxyphenyl)propan-1-one 
• 67-68-5 dimethyl sulfoxide 
• 104397-78-6 1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one 
• 203437-89-2 1-(3,4-Dimethoxy-phenyl)-3-ethylsulfanyl-propan-1-one 
• 91-16-7 1,2-dimethoxybenzene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 31706-95-3 1'-Hydroxymethyleugenol 
• 625-36-5 2-chloropropionyl chloride 

Downstream Products

• 4650-71-9 SK 31597 
• 31706-95-3 1'-Hydroxymethyleugenol 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 

Relevant academic research and scientific papers

Design and synthesis of Mannich base-type derivatives containing imidazole and benzimidazole as lead compounds for drug discovery in Chagas Disease

The protozoan parasite Trypanosoma cruzi is the causative agent of Chagas disease, the most important parasitic infection in Latin America. The only treatments currently available are nitro-derivative drugs that are characterised by high toxicity and limited efficacy. Therefore, there is an urgent need for more effective, less toxic therapeutic agents. We have previously identified the potential for Mannich base derivatives as novel inhibitors of this parasite. To further explore this family of compounds, we synthesised a panel of 69 new analogues, based on multi-parametric structure-activity relationships, which allowed optimization of both anti-parasitic activity, physicochemical parameters and ADME properties. Additionally, we optimized our in vitro screening approaches against all three developmental forms of the parasite, allowing us to discard the least effective and trypanostatic derivatives at an early stage. We ultimately identified derivative 3c, which demonstrated excellent trypanocidal properties, and a synergistic mode of action against trypomastigotes in combination with the reference drug benznidazole. Both its druggability and low-cost production make this derivative a promising candidate for the preclinical, in vivo assays of the Chagas disease drug-discovery pipeline.

Laccase-catalyzed oxidation of allylbenzene derivatives: Towards a green equivalent of ozonolysis

Laccase-based biocatalytic reactions have been tested with and without mediators and optimized in the oxidation of allylbenzene derivatives, such as methyl eugenol taken as a model substrate. The reaction primarily consisted in the hydroxylation of the propenyl side chain, either upon isomerization of the double bond or not. Two pathways were then observed; oxidation of both allylic alcohol intermediates could either lead to the corresponding α,β-unsaturated carbonyl com-pound, or the corresponding benzaldehyde derivative by oxidative cleavage. Such a process consti-tutes a green equivalent of ozonolysis or other dangerous or waste-generating oxidation reactions. The conversion rate was sensitive to the substitution patterns of the benzenic ring and subsequent electronic effects.

Visible-Light-Driven Cleavage of C?O Linkage for Lignin Valorization to Functionalized Aromatics

Lignin is the most abundant source of renewable aromatics. Catalytic valorization of lignin into functionalized aromatics is attractive but challenging. Photocatalysis is a promising sustainable approach. The strategies for designing well-performing photocatalysts are desired but remain limited. Herein, a facile energy band engineering strategy for promoting the photocatalytic activity of zinc–indium–sulfide (ZnmIn2Sm+3) for cleavage of the lignol β-O-4 bond under mild conditions was developed. The energy band structure of ZnmIn2Sm+3 could be tuned by controlling the atomic ratio of Zn/In. It was found that Zn4In2S7 performed best for cleavage of the β-O-4 bond under visible-light irradiation, owing to its appropriate energy band structure for offering adequate visible-light absorption and suitable redox capability. Functionalized aromatic monomers with near 18.4 wt % yield could be obtained from organosolv birch lignin. Mechanistic studies revealed that the β-O-4 bond was efficiently cleaved mainly through a one-step redox-neutral pathway via a Cα radical intermediate. The thiol groups on the surface of Zn4In2S7 played a key role in cleavage of the β-O-4 bond.

Mechanistic studies of base-catalysed lignin depolymerisation in dimethyl carbonate

The depleting fossil reservoirs have stimulated global research initiatives on renewable lignin feedstocks as sustainable alternatives to petroleum-derived aromatics. Base-catalysed depolymerisation (BCD) is regarded as an economical and efficient approach for the valorisation of technical lignins. The major limiting factor encountered during this process is the re-condensation of the formed phenolic products, which results in lower monomer yields. To diminish these side reactions, we selected alkali earth metal catalysts in dimethyl carbonate (DMC) to produce methylated phenol derivatives as the final products. Herein, we demonstrate for the first time a base-promoted depolymerisation process affording low-molecular weight oils in high yields (52-67 wt%) wherein the employed bases are used in truly catalytic quantities (with catalyst loadings of around 5 mol%). The general applicability of this methodology was proved on four different lignin samples (1 Kraft, 3 organosolv) using caesium carbonate and lithium tert-butoxide as catalysts. The 2D NMR studies on the post-reaction lignin samples showed a similar degradation of the major lignin linkages for both bases. A difference in the reduction of phenolic moieties was revealed by quantitative 31P NMR analysis. Furthermore, GPC analysis demonstrated a significant shift towards lower mass fragments for the Cs2CO3-catalysed lignin degradation. A detailed GC-MS analysis for these samples identified a range of methoxy capped-monomeric degradation products. The scope of this reaction system was further expanded to lignocellulosic biomass such as milled beechwood chips, which notably showed similar product distributions. Based on the correlation of the experimental observations for extracted lignin samples and model compound studies, a mechanistic pathway for the Cs2CO3-catalysed system was suggested. DFT calculations provided reaction pathways for the observed cleavage products.

Transition Metal-Free α-Csp3-H Methylenation of Ketones to Form C=C Bond Using Dimethyl Sulfoxide as Carbon Source

A direct α-Csp3-H methylenation of arylketones to form C=C bond using dimethyl sulfoxide as one-carbon source is achieved under transition metal-free reaction condition. Various aryl ketone derivatives react readily with DMSO, producing the α,β-unsaturated carbonyl compounds in yields of 42 to 90%. This method features a transition metal-free reaction condition, wide substrate scope and using DMSO as novel one-carbon source to form C=C bond, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.

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.

Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols

The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.

The heck coupling reaction using aryl vinyl ketones: Synthesis of flavonoids

In our previous communication, an α,β-unsaturated aryl ketone was employed as the substrate olefin, which underwent arylation in the Heck coupling reaction. The use of this reagent has allowed us to design a new strategy for the synthesis of flavonoids. In this paper, we illustrate the versatility of the procedure, which was used for the preparation of several chalcones. According to our synthetic scheme, several aryl iodides, selected in order to obtain chalcones differently substituted in ring B, were treated with α,β-unsaturated ketones. All reported syntheses gave high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Substituted furans as inhibitors of the PDE4 enzyme

The synthesis and in vitro activity of a series of substituted furans as a novel structural class of PDE4 inhibitors is described. Comparison of emetic threshold with known PDE4 inhibitors is presented.

Reactions of β-ethylsulfanylpropionyl tetrafluoroborate with electron-rich aromatics: A novel synthesis of aryl vinyl ketones

A new synthesis of aryl vinyl ketones is described. The acylation of active aromatics with the complex of β-ethylsulfanylpropionyl fluoride 1 and boron trifluoride leads to formation of 1-aryl-3-(ethylsulfanyl)propan-1-ones. Subsequent methylation with methyl triflate and elimination with an aqueous solution of KHCO3 results in formation of aryl vinyl ketones in 86-99% yield.