1145-93-3

Usage

Uses

Used in Pharmaceutical Synthesis:
DIETHYL 4-METHOXYBENZYLPHOSPHONATE is used as a reactant for the synthesis of C-aryl glycosides, which are important in the development of pharmaceutical compounds due to their potential biological activities.
Used in the Synthesis of Goniothalamin Analogs:
In the field of natural product chemistry, DIETHYL 4-METHOXYBENZYLPHOSPHONATE is used as a reactant for the synthesis of γ-Monofluorinated goniothalamin analogs. These analogs are synthesized via ring-opening hydrofluorination and may exhibit unique biological properties.
Used in the Synthesis of Stilbenoid Derivatives:
DIETHYL 4-METHOXYBENZYLPHOSPHONATE is utilized in the synthesis of stilbenoid derivatives, which possess neuroprotective activity. These compounds have potential applications in the treatment of neurological disorders and conditions.
Used in the Synthesis of Resveratrol-chroman Hybrids:
DIETHYL 4-METHOXYBENZYLPHOSPHONATE is also used as a reactant in the synthesis of resveratrol-chroman hybrids, which exhibit antioxidant activity. These hybrids may have applications in the development of antioxidants for various industries, including pharmaceuticals and cosmetics.
Used in the Synthesis of Oligostilbenoids:
DIETHYL 4-METHOXYBENZYLPHOSPHONATE is employed in the synthesis of oligostilbenoids through regioselective cyclodehydration and arylation. Oligostilbenoids are a class of compounds with potential applications in various fields, including pharmaceuticals, due to their diverse biological activities.

InChI:InChI=1/C12H19O4P/c1-4-15-17(13,16-5-2)10-11-6-8-12(14-3)9-7-11/h6-9H,4-5,10H2,1-3H3

Upstream product

• 78-40-0 triethyl phosphate 
• 824-94-2 p-methoxybenzyl chloride 
• 76950-80-6 1-(4-Methoxy-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 
• 122-52-1 triethyl phosphite 
• 3173-38-4 diethyl 4-(hydroxy)benzylphosphonate 
• 74-88-4 methyl iodide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 2746-25-0 p-Methoxybenzyl bromide 
• 762-04-9 phosphonic acid diethyl ester 
• 104-93-8 p-methylanizole 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 696-62-8 para-iodoanisole 
• 145028-33-7 diethyl 1-(4-methoxyphenyl)-2-oxopropylphosphonate 

Downstream Products

• 7577-08-4 1-(cyclohexylidenemethyl)-4-methoxy-benzene 
• 110993-22-1 (E)-1-hydroxy-3-(4-methoxy)styrylbenzene 
• 2131-84-2 1-methoxy-4-(4-styrylstyryl)benzene 
• 40299-61-4 (4-methoxybenzyl)phosphonic acid 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 22145-08-0 (E,E)-1-(4-methoxyphenyl)-4-phenyl-1,3-butadiene 
• 19036-99-8 2-(4-Methoxy-styryl)-pyridin 
• 5863-78-5 (E)-3-(4-methoxystyryl)pyridine 
• 223377-41-1 (E)-2-[2-(4-methoxylphenyl)ethenyl]thiophene 
• 129047-44-5 (E)-2,4,4',5-tetramethoxystilbene 
• 917471-59-1 2-(p-methoxystyryl)-α,α,α-trifluorotoluene 
• 150258-83-6 4-methoxyl-3′,4′-dihydroxy-trans-stilbene 
• 39769-24-9 (E)-4-fluoro-4'-methoxystilbene 
• 22920-31-6 (E)-1-(4-methoxyphenyl)-2-(1-naphthyl)ethene 

Relevant academic research and scientific papers

Synthesis of ethylene bis [(2-hydroxy-5,1,3-phenylene) bis methylene] tetraphosphonic acid and their anticorrosive effect on carbon steel in 3%NaCl solution

The inhibition performance of the newly synthesized Ethylene bis [(2-hydroxy-5,1,3-phenylene) bis methylene] tetraphosphonic acid (ETPA) toward carbon steel in 3% NaCl was investigated at different concentrations using potentiodynamic polarization (PDP) and impedance spectroscopy (EIS) methods. It was found that the inhibition capability was increased with increasing inhibitor dose and reach 92% at 10?3 mol/L. Also, Polarization curves showed that ETPA acts as a mixed type inhibitor with predominantly control of anodic reaction. The new inhibitor was investigated by different spectroscopic methods such as 1H, 13C and 31PNMR. The quantum parameters such as absolute electronegativity (χ), energy gap ΔE (EHOMO-ELUMO), global softness (σ), global hardness (η), electrophilicity index (ω) and the number of transfer electrons (ΔN) are calculated by density functional theory (DFT). The experimental also correlated with density functional theory results. The calculations show that ETPA has high density of negative charge located on the oxygen atoms of the phosphonate group facilitating the adsorption of ETPA on the surface of carbon steel. The inhibition efficiency of ETPA was discussed in terms of blocking of electrode surface by adsorption of ETPA molecules through active centers. The adsorption of ETPA on the surface of carbon steel obeyed the Langmuir isotherm paradigm.

Synthesis of Indole-, Benzo[ b]thiophene-, and Benzo[ b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B

A convenient synthetic strategy to obtain viniferifuran and (±)-dehydroampelopsin B analogues based on the heterocyclic cores of indole, benzo[b]thiophene, and benzo[b]selenophene is presented. The key transformations utilized in the described syntheses include Sonogashira couplings, Cacchi and alkyne electrophilic cyclizations, Horner-Wadsworth-Emmons (HWE) reaction, chemoselective Suzuki-Miyaura couplings, and acid-promoted intramolecular cyclization to form the seven-membered ring of (±)-dehydroampelopsin B.

Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues

The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4′- acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4′-triacetylresveratrol (3), 3,5,4′-tributanoylresveratrol (6), and 3, 4, 5′-trioctanoylresveratrol (9) afforded derivatives 4, 5, 7, 8, 10, and 11. Further resveratrol analogues (12-18) were obtained through methylation and hydrogenation reactions, whereas the 3,4,4′- trimethoxystilbene (19) was obtained by complete synthesis. Resveratrol and its lipophylic analogues were subjected to cell-growth inhibition bioassays towards DU-145 human prostate cancer cells. Compounds 2-19 showed cell-growth inhibition activity comparable to or higher than resveratrol (GI50 = 24.09 μM), displaying low or very low toxicity against non-tumorigenic human fibroblast cells. Comparison of the trimethoxy stilbenes 12 (GI50 = 2.92 μM) and 19 (GI50 = 25.39 μM) indicates that the position of the substituents is important for the activity. The marked activity of methyl ethers 12, 13, and 18 in comparison with that of the corresponding esters suggests that the different chemical reactivity, rather than steric factors, strongly influences the activity.

Remote meta-C–H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary

An easily removable pyrimidine-based auxiliary has been employed for the remote meta-C?H cyanation of arenes. The scope of this Pd-catalyzed cyanation reaction using copper(I) cyanide as the cyanating agent was demonstrated with benzylsilanes, benzylsulfonates, benzylphophonates, phenethylsulfonates, and phenethyl ether derivatives. The method was utilized for the synthesis of pharmaceutically valuable precursors.

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids

An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.

Determination and application of the excited-state substituent constants of pyridyl and substituted phenyl groups

Thirty six 1-pyridyl-2-arylethenes XCH=CHArY (abbreviated XAEY) were synthesized, in which, X is 2-pyridyl, 3-pyridyl and 4-pyridyl and Y is OMe, Me, H, Br, Cl, F, CF3, and CN. Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelengths of absorption maximum λmax were recorded. Also, the 234 λmax values of 1-substituted phenyl-2-arylethylene compounds (XAEY, where X is substituted phenyl) were collected. The excited-state substituent constants (Formula presented.) of three pyridyl groups and 23 substituted phenyl groups (total of 26) were obtained by means of curve-fitting method. Taking the λmax values of 358 samples of bi-arylethene derivatives as a data set and 126 samples of bi-aryl Schiff bases (including nine compounds synthesized by this work) as another data set, quantitative correlation analyses were performed by employing the obtained (Formula presented.) as a parameter, and good results were obtained for the two data sets. The reliability of the obtained (Formula presented.) values was verified. The results of this paper can provide excited-state substituent constants for the study and application of optical properties of conjugated organic compounds containing aryl groups.

Series of Compounds for Treatment of Skin Diseases and Other Conditions

Compounds and methods related to the prevention and treatment of diseases and conditions, some of which are facilitated by melanogenesis are disclosed. Specifically, the present subject matter includes a series of compounds and compositions and their use for anti-melanogenic and antioxidant activity. This subject matter also includes the treatment of skin disorder due to acne vulgaris and related inflammatory and post inflammatory hyperpigmentation. Methods for synthesizing contemplated compounds are also disclosed.

Resveratrol A-cyclo-N(CH3)2-yl derivative as well as preparation method and application thereof

The invention provides a resveratrol A-cyclo-N(CH3)2-yl derivative as well as a preparation method and application thereof, and belongs to the technical field of medicines. The invention provides theresveratrol A-cyclo-N(CH3)2-yl derivative with a structure shown in a formula I, which acts on an NHE-1 receptor as a sodium hydrogen exchange protein 1 (NHE-1) receptor antagonist in a targeting manner and simultaneously inhibits two signal transduction pathways, namely a phosphatidylinositol 3kinase/protein serine threonine kinase (PI3K/AKT) signal pathway and a Janus kinase/signal transductionand transcription activator (JAK/STAT); therefore, the effect of treating the alcoholic fatty liver is achieved.

Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation

The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.