6652-32-0

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dimethoxybenzyl chloride is used as a synthetic intermediate for the preparation of benzyl 7-(3,5-dimethoxyphenylacetoxy)octanoate, which is a precursor of curvularin. Curvularin is a natural product with potential biological activities, including anti-inflammatory and anticancer properties.
Used in Organic Synthesis:
3,5-Dimethoxybenzyl chloride is used as a reagent in the preparation of diethyl (3,5-dimethoxybenzyl) phosphonate through the Wittig-Horner reaction. This reaction is a widely used method for the synthesis of alkenes, which are important building blocks in the preparation of various organic compounds, including pharmaceuticals, agrochemicals, and materials. The introduction of the 3,5-dimethoxybenzyl moiety via this reaction can provide access to a range of novel compounds with potential applications in various fields.

Upstream product

• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 1132-21-4 3,5-dimethoxybenzoic acid 

Downstream Products

• 13388-75-5 3,5-dimethoxyphenylacetonitrile 
• 22976-41-6 3,5,3',5'-tetramethoxy-bibenzyl 
• 717-94-2 3-(3,5-dimethoxyphenyl)propionic acid 
• 55142-97-7 5-(3,5-dimethoxy-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 26050-72-6 (3,5-dimethoxybenzyl)trimethylammonium chloride 
• 157065-45-7 (3,5-dimethoxybenzyl)trimethylsilane 
• 128503-54-8 Methyl 2-O-(3,5-dimethoxybenzyl)-3,5-di-O-methyl-β-D-xylofuranoside 
• 128503-53-7 Methyl 2-O-(3,5-dimethoxybenzyl)-3,5-di-O-methyl-α-D-xylofuranoside 
• 82112-37-6 (3,5-dimethoxyphenyl)-(p-toluenesulfonyl)methane 
• 157065-46-8 <2-(3,5-dimethoxyphenyl)ethyl>trimethylsilane 
• 5859-68-7 [(3,5-dimethoxyphenyl)methyl]propanedioic acid diethyl ester 
• 66769-61-7 1-(iodomethyl)-3,5-dimethoxybenzene 
• 174754-65-5 dimethyl 2-(3,5-dimethoxybenzyl)malonate 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 

Relevant academic research and scientific papers

Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction

The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.

Parallel in vitro and in silico investigations into anti-inflammatory effects of non-prenylated stilbenoids

Stilbenoids represent a large group of bioactive compounds, which occur in food and medicinal plants. Twenty-five stilbenoids were screened in vitro for their ability to inhibit COX-1, COX-2 and 5-LOX. Piceatannol and pinostilbene showed activity comparable to the zileuton and ibuprofen, respectively. The anti-inflammatory potential of stilbenoids was further evaluated using THP-1 human monocytic leukemia cell line. Tests of the cytotoxicity on the THP-1 and HCT116 cell lines showed very low toxic effects. The tested stilbenoids were evaluated for their ability to attenuate the LPS-stimulated activation of NF-κB/AP-1. Most of the tested substances reduced the activity of NF-κB/AP-1 and later attenuated the expression of TNF-α. The effects of selected stilbenoids were further investigated on inflammatory signaling pathways. Non-prenylated stilbenoids regulated attenuation of NF-?B/AP-1 activity upstream by inhibiting the phosphorylation of MAPKs. A docking study used to in silico analyze the tested compounds confirmed their interaction with NF-?B, COX-2 and 5-LOX.

Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase

Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-κB (NF-κB) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-κB/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) was further evaluated using LPS-stimulated THP-1 macrophages.

Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents

A series of both novel and reported combretastatin analogues, including diarylpyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles, were synthesized via improved protocols to evaluate their antimitotic antitubulin activity using in vivo sea urchin embryo assay and a panel of human cancer cells. A systematic comparative structure-activity relationship studies of these compounds were conducted. Pyrazoles 1i and 1p, isoxazole 3a, and triazole 7b were found to be the most potent antimitotics across all tested compounds causing cleavage alteration of the sea urchin embryo at 1, 0.25, 1, and 0.5 nM, respectively. These agents exhibited comparable cytotoxicity against human cancer cells. Structure-activity relationship studies revealed that compounds substituted with 3,4,5-trimethoxyphenyl ring A and 4-methoxyphenyl ring B displayed the highest activity. 3-Hydroxy group in the ring B was essential for the antiproliferative activity in the diarylisoxazole series, whereas it was not required for potency of diarylpyrazoles. Isoxazoles 3 with 3,4,5-trimethoxy-substituted ring A and 3-hydroxy-4-methoxy-substituted ring B were more active than the respective pyrazoles 1. Of the azoles substituted with the same set of other aryl pharmacophores, diarylpyrazoles 1, 4,5-diarylisoxazoles 3, and 4,5-diaryl-1,2,3-triazoles 7 displayed similar strongest antimitotic antitubulin effect followed by 3,4-diarylisoxazoles 5, 1,5-diaryl-1,2,3-triazoles 8, and pyrroles 10 that showed the lowest activity. Introduction of the amino group into the heterocyclic core decreased the antimitotic antitubulin effect of pyrazoles, triazoles, and to a lesser degree of 4,5-diarylisoxazoles, whereas potency of the respective 3,4-diarylisoxazoles was increased.

Preparation method of resveratrol

The invention discloses a preparation method of resveratrol. The preparation method comprises that (1), 3, 5-dimethoxybenzhydrol is chloroformed under the action of triphosgene to form 3, 5-dimethoxybenzyl chloride, (2), 3, 5-dimethoxybenzyl chloride reacts with triphenylphosphine to produce phosphorus ylide, (3), phosphorus ylide and p-methoxybenzaldehyde form a cis-trans-isomer mixture of 3, 4',5-trimethoxydistyrene under the action of lithium hydroxide, (4), 3, 4', 5-trimethoxystilbene, aluminum and iodine are added to acetonitrile, the mixture is cooled to the room temperature so that yellow solids are separated, the yellow solids are filtered, the filtrate acetonitrile is directly recovered and recycled, 6N hydrochloric acid and ethyl acetate are added into the filter cake, the mixture is stood for layering, wherein the water layer contains ethyl acetate extract, the organic phases are mixed, the organic phases are washed through a saturated salt solution, anhydrous sodium sulfate is dried and filtered, the solvent is removed in vacuum through a water pump, and the organic phase is recrystallized through ethanol and water so that resveratrol is obtained. The preparation method utilizes easily available raw materials, is easy to operate and control, is environmentally friendly, produces easily purified products, has a high yield and is suitable for industrial production.

Preparation method for health product pterostilbene

The invention provides a preparation method for a health product pterostilbene. According to the invention, 1, a deprotection method used in the invention is green, environment-friendly and pollution-free, the preparation method is almost free of production of waste gas, waste water and industrial residues, and the product 1,4-pentadiene has economic value; 2, a catalyst used in the invention has good cycle repeatability and can be cyclically used 50 times or more; 3, the preparation method is simple in operation requirements, mild in reaction conditions, good in specificity, simple in post-treatment and purification of the product, and suitable for industrial production; and 4, the pterostilbene prepared by using the method is free of impurities like 3-methoxy-4',5-dihydroxystilbene and resveratrol and has high purity.

Synthesis method of piceatannol

The present invention provides a synthesis method of piceatannol. The method comprises the following steps: reacting 3,5-dimethoxybenzyl alcohol with phosphorus oxychloride to obtain 3,5-dimethoxybenzyl chloride; adding the obtained 3,5-dimethoxybenzyl ch

Oxyresveratrol synthesis method

The invention provides an oxyresveratrol synthesis method which comprises the following steps: firstly performing a reflux reaction between raw materials 3,5-dimethoxybenzyl alcohol and phosphorus oxychloride; after the reaction is complete, pressurizing and recycling the solvent; filtering, washing to neutrality and drying to obtain 3,5-dimethoxybenzyl chloride; performing a reflux reaction between the obtained 3,5-dimethoxybenzyl chloride and trimethyl phosphite in a solvent DMF (dimethyl formamide); after the reaction is complete, adding a catalyst sodium methylate solution, and adding a mixed solution of 2,4-dimethoxy benzaldehyde and DMF to obtain tetramethoxy diphenyl ethylene; and finally, performing a reflux reaction between the obtained tetramethoxy diphenyl ethylene and aluminum trichloride and xylene, wherein oxyresveratrol is obtained after the reaction is complete. According to the method provided by the invention, a Witting-Homer reaction is adopted, the raw materials are easily available, the yield is high, the cost is low, and the method is suitable for industrial production.

Phosphine functionalized polyphosphazenes: soluble and re-usable polymeric reagents for highly efficient halogenations under Appel conditions

In this paper we present the preparation and application of a novel soluble phosphine functionalized polyphosphazene (poly[3-(diphenylphosphino)propylamino]phosphazene) and investigate its application as a polymeric reagent. Upon chlorination of the pendant phosphine groups, the polymer was found to facilitate the rapid and efficient transformation of alcohols to the corresponding chlorides and bromides under Appel-type conditions. Reaction times followed by 31P NMR spectroscopy are shown to be rapid (several minutes) and the yields for the transformation of alcohols to the corresponding halides are in the range 80–99?%. The facile recovery of the oxidized polymeric agent by precipitation is also described, offering a significant advantage over notoriously difficult to remove small molecule phosphine oxide by-products. Furthermore the regeneration of the reactive phosphine chloride pendant groups is demonstrated, which could be efficiently re-used in a further chlorination reaction. Graphical abstract: [Figure not available: see fulltext.]

Method for preparing resvertrol (by machine translation)

The invention discloses method for preparing resvertrol, in order to 3,5-dimethoxy-methanol as the raw material, through chloropivaloyl, to obtain 3,5-dimethoxy oxygen radical chlorine animal pen, through the 3,5-dimethylbenzaldehyde by oxygen radical chlorine animal pen 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works. This invention, through the triphosgene 3,5-dimethoxy-methanol chloropivaloyl, instead of ethanol using sodium hydride and sodium, synthetic 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works, preparation method has high yield, low cost. (by machine translation)