108957-75-1

Basic information

• Product Name: Diethyl 3,5-Dimethoxybenzylphosphonate
• Synonyms: Diethyl 3,5-Dimethoxybenzylphosphonate;P-[(3,5-Dimethoxyphenyl)methyl]phosphonic Acid Diethyl Ester
• CAS NO: 108957-75-1
• Molecular Formula: C₁₃H₂₁O₅P
• Molecular Weight: 288.28
• Product Categories: Aromatics;Wittig Reagents
• Mol File: 108957-75-1.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 404.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.123±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Diethyl 3,5-Dimethoxybenzylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 3,5-Dimethoxybenzylphosphonate(108957-75-1)
• EPA Substance Registry System: Diethyl 3,5-Dimethoxybenzylphosphonate(108957-75-1)

Safety Data

• Hazardous Substances Data: 108957-75-1(Hazardous Substances Data)

Usage

Description

Diethyl 3,5-Dimethoxybenzylphosphonate, with the CAS number 108957-75-1, is a compound that is utilized in the field of organic synthesis. It is characterized by its transparent oil appearance, which indicates its potential for use in various chemical reactions and processes.

Uses

Used in Organic Synthesis:
Diethyl 3,5-Dimethoxybenzylphosphonate is used as a synthetic building block for the creation of various organic compounds. Its unique chemical structure allows it to be a valuable component in the synthesis of complex molecules, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Diethyl 3,5-Dimethoxybenzylphosphonate is used as an intermediate in the synthesis of drugs. Its versatile chemical properties enable it to be a key component in the development of new medications, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
Diethyl 3,5-Dimethoxybenzylphosphonate is also utilized in the agrochemical industry as a precursor for the development of new pesticides and other agricultural chemicals. Its role in organic synthesis allows for the creation of innovative products that can improve crop protection and yield.
Used in Specialty Chemicals:
In the specialty chemicals sector, Diethyl 3,5-Dimethoxybenzylphosphonate is employed as a key ingredient in the production of various high-value chemicals. Its unique properties make it suitable for use in the development of advanced materials, coatings, and other specialized applications.

Upstream product

• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 78-40-0 triethyl phosphate 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 122-52-1 triethyl phosphite 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 7311-34-4 3,5-dimethoxybenzaldehdye 

Downstream Products

• 80715-09-9 (E)-3,3',5,5'-tetramethoxystilbene 
• 848487-76-3 (E)-1-(4'-(methoxymethoxy)styryl)-3,5-dimethoxybenzene 
• 1260096-41-0 C₂₄H₃₀O₄ 
• 20578-92-1 (E)-3,5,2',4'-tetramethoxystilbene 
• 20578-92-1 (Z)-2,3',4,5'-tetramethoxystilbene 
• 4721-07-7 oxyresveratrol 
• 1224713-90-9 5-[(1E)-2-(4-bromophenyl)ethenyl]-1,3-benzenediol 
• 1415605-00-3 5-(4-((dimethylamino)phenyl)ethyl)benzene-1,3-diol 
• 1415605-04-7 (E)-4-(3,5-dimethoxystyryl)-N,N-dipropylaniline 
• 1415604-93-1 C₂₀H₂₅NO₂ 
• 1258410-98-8 (E)-1-(4-tert-butylstyryl)-3,5-dimethoxybenzene 
• 1415605-01-4 (E)-2-(3,5-dimethoxystyryl)-N,N-dimethylaniline 
• 1415605-02-5 (E)-3-(3,5-dimethoxystyryl)-N,N-dimethylaniline 
• 1415605-05-8 (E)-4-(3,5-dimethoxystyryl)-N-ethylaniline 

Relevant articles and documents

Near infrared dyes by combination of squaraine and ferrocene chromophores

Squaraines represent a class of compounds which attracts a lot of attention in materials science. A synthetic sequence for the preparation of the symmetrical squaraines 12a,b, which contain ferrocene units as electron donors, is described. The compounds exhibit, in dichloromethane or chloroform, two intense absorption bands. One of them is located at 641/650 nm - a normal region for squaraines; however, the other band is strongly shifted to long wavelengths and has its maximum at 921/961 nm. Alkyl sidechains enhance the solubility of 12a,b, which represent a new type of NIR dyes. (C) 2000 Elsevier Science Ltd.

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.

Dimerization of resveratrol trimethyl ether by phosphotungstic acid, structure confirmation of resformicol A and B

Dimerization of the trimethyl ether of resveratrol catalyzed by phosphotungstic acid gave two tetralins and a naphthalene derivative. The structure of the tetralins was obtained by X-ray crystallography and confirms the reported stereochemical configuration of resformicol A and B.

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.

Resveratrol-Related Polymethoxystilbene Glycosides: Synthesis, Antiproliferative Activity, and Glycosidase Inhibition

A small library of polymethoxystilbene glycosides (20-25) related to the natural polyphenol resveratrol have been synthesized and subjected, together with their aglycones 17-19, to an antiproliferative activity bioassay toward Caco-2 and SH-SY5Y cancer cells. Six of the compounds exhibit antiproliferative activity against at least one cell line. In particular, compounds 17 and 18 proved highly active on at least one of the two cell cultures. Compound 18 showed a GI50 value of 3 ΜM against Caco-2 cells, a value comparable to that of the anticancer drug 5-fluorouracil. The closely related compound 19 proved inactive, and its conjugates 22 and 25 showed weak cell growth inhibition. The results indicate that minimal differences in the structure of both polymethoxystilbenes and their glycosides can substantially affect the antiproliferative activity. The possible hydrolytic release of the aglycones 17-19 by β-glucosidase or β-galactosidase was also evaluated. Compounds 20-25 were also tested as potential β-glucosidase, β-galactosidase, and α-glucosidase inhibitors. A promising inhibitory activity toward α-glucosidase was observed for 21 (IC50 = 78 ΜM) and 25 (IC50 = 70 ΜM), which might be indicative of their potential as lead compounds for development of antidiabetic or antiobesity agents.

Vinyl-Stilbene Compounds and Uses Thereof

The present invention relates to a biphenyl - stilbene (Vinyl-stilbene) - based compound and a pharmaceutical composition for preventing or treating norovirus infection comprising the same as an active ingredient. The present invention can be usefully used as a pharmaceutical composition for treating norovirus infection by showing superior norovirus inhibitory activity and lower cell toxicity as compared to previously known compounds.

Preparation method of resveratrol

The invention belongs to the technical field of preparation of medicine key intermediates, and particularly relates to a preparation method of resveratrol. The synthesis and preparation method of theresveratrol comprises the following steps: a, taking 3, 5-dimethoxybenzyl alcohol and phosphorus tribromide as raw materials, and synthesizing 3, 5-dimethoxybenzyl bromide (a compound A); b, taking the compound A, triethyl phosphite and tetrabutylammonium bromide as raw materials, and synthesizing to obtain 3, 5-dimethoxy benzyl diethyl phosphate (a compound B); c, taking the compound B, dimethyldiamide, sodium hydride and anisaldehyde as raw materials, and carrying out a reaction to synthesize to obtain (E) 3, 4 ', 5-trimethoxystilbene (compound C); and d, using the compound C and pyridine hydrochloride as raw materials, carrying out a reaction to synthesize 3, 4, 5-trihydroxy-1, 2-stilbene, namely the resveratrol. The method has the characteristics of cheap and easily available raw materials, mild reaction conditions, simple operation, high yield and low cost, and is beneficial to industrial production.