57277-25-5

Usage

Uses

Used in Organic Synthesis:
Diethyl (2-naphtylmethyl)phosphonate is used as a reagent for the formation of carbon-phosphorus bonds, which are crucial in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
Diethyl (2-naphtylmethyl)phosphonate is utilized as a precursor in the synthesis of medicinal drugs, highlighting its importance in the development of new pharmaceuticals.
Used as an Enzyme Inhibitor:
Diethyl (2-naphtylmethyl)phosphonate has been studied for its potential as an enzyme inhibitor, which could have applications in treating specific diseases by modulating enzyme activity.
Used in Flame Retardants:
Diethyl (2-naphtylmethyl)phosphonate has been investigated for its potential use in flame retardants, indicating its possible role in improving the safety of materials used in various industries.
Used in Pesticides:
Diethyl (2-naphtylmethyl)phosphonate has also been explored for its potential application in pesticides, suggesting it could be a component in developing new pest control agents.

Upstream product

• 939-26-4 2-bromomethylnaphthyl bromide 
• 122-52-1 triethyl phosphite 
• 3167-63-3 diethyl chloromethylphosphonate 
• 580-13-2 2-bromonaphthalene 
• 78-40-0 triethyl phosphate 
• 19350-74-4 2-naphthaldehyde tosylhydrazone 
• 762-04-9 phosphonic acid diethyl ester 
• 66-99-9 β-naphthaldehyde 
• 1592-38-7 2-Naphthalenemethanol 

Downstream Products

• 16672-84-7 2-Naphthylmethylphosphonic acid 
• 126479-93-4 9-benzenesulfonyl-3-(2-naphthylethenyl)carbazole 
• 1372151-85-3 C₂₂H₂₄FO₃P 

Relevant academic research and scientific papers

The development of HEC-866 and its analogues for the treatment of idiopathic pulmonary fibrosis

Idiopathic pulmonary fibrosis (IPF) is a chronic progressive lung disease with a typical survival time between three to five years. Two drugs, pirfenidone and nintedanib have been approved for the treatment of IPF, but they have limited efficacy. Thus, th

Structural variability of pendant groups within the interlayer region of zirconium arene-phosph(on)ates: Chemical and structural characterization of oxy- And methyl-linked 2-naphthyl phosphonates, and mixed oxy-linked derivatives

Several new zirconium phosphonates incorporating the naphthalene ring and having the general formula Zr(O3PR)1(O3PR′)1 [R and R′ = -CH2C10H7, -OC10H7, -CH3, -OC2H5, -OH] have been synthesized. These materials were chemically characterized using thermal gravimetric analysis (percentage of organic content), infrared spectroscopy (presence of the desired organic functional groups), and solid-state 31P NMR (phosphorus environments), while the structural parameters were determined using X-ray powder diffraction (interlayer d spacings). The two new zirconium bis(phosphonates), Zr(O3PC10H7)2 and Zr(O3PCH2C10H7)2, were found to have d spacings of 19.6 and 20.0 ?, respectively. Three of the four zirconium mixed phosphonates examined are found to be single-phase structures with random mixtures of the organic moieties within the interlayer, and possess d spacings (14.3, 15.3, and 16.1 ?) that are between those of the two parent zirconium bis(phosphonates). The fourth is found to be a staged or segregated structure and possesses a d spacing that is approximately a sum of the two parent zirconium bis(phosphonates), with a d spacing of 28.2 ?. Solid-state 31P NMR of Zr(O3PCH2C10H7)2 revealed the presence of two isotropic resonances, which is interpreted in terms of two distinct, "locked-in" conformations of the -CH2C10H7 group. The experimental d spacings of the zirconium bis(phosphonates) correlate well with a simple predictive model based on the effective length and predominant conformation of the organic functional group.

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.

Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes

Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.

Synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds

The invention discloses a synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds. According to the synthetic method, alcohols which are cheap, easy to get, wide in source, stable and low in toxicity serve as alkylating reagents, iodine salt which is cheap and easy to get serves as catalysts, no solvent is needed, and the alkyl group phosphorous acid diester compounds can be selectively directly obtained after a reaction. The reaction method is simple, the condition is mild, no organic solvent is needed and operation is simple. According to the method, the requirements for reaction conditions are low, various types of alcohols such as a benzyl group type, an allyl type and a fat type can be utilized as the alkylate reagents to implement the synthesis of different types of substituted alkyl group phosphorous acid diester, and the method can be further expanded to the synthesis of the alkyl group phosphinic acid ester compounds through the reaction between the substituted phosphonous acid diester and the alcohols.

Benzyl Mono-P-Fluorophosphonate and Benzyl Penta-P-Fluorophosphate Anions Are Physiologically Stable Phosphotyrosine Mimetics and Inhibitors of Protein Tyrosine Phosphatases

α,α-Difluoro-benzyl phosphonates are currently the most popular class of phosphotyrosine mimetics. Structurally derived from the natural substrate phosphotyrosine, they constitute classical bioisosteres and have enabled the development of potent inhibitors of protein tyrosine phosphatases (PTP) and phosphotyrosine recognition sites such as SH2 domains. Being dianions bearing two negative charges, phosphonates, however, do not permeate membranes and thus are often inactive in cells and have not been a successful starting point toward therapeutics, yet. In this work, benzyl phosphonates were modified by replacing phosphorus-bound oxygen atoms with phosphorus-bound fluorine atoms. Surprisingly, mono-P-fluorophosphonates were fully stable under physiological conditions, thus enabling the investigation of their mode of action toward PTP. Three alternative scenarios were tested and mono-P-fluorophosphonates were identified as stable reversible PTP1B inhibitors, despite of the loss of one negative charge and the replacement of one oxygen atom as an H-bond donor by fluorine. In extending this replacement strategy, α,α-difluorobenzyl penta-P-fluorophosphates were synthesized and found to be novel phosphotyrosine mimetics with improved affinity to the phosphotyrosine binding site of PTP1B.

NITROGENOUS HETEROCYCLIC DERIVATIVES AND THEIR APPLICATION IN DRUGS

The present invention relates to the field of medicine, provided herein are novel nitrogenous heterocyclic compounds, their preparation methods and their uses as drugs, especially for treatment and prevention of tissue fibrosis. Also provided herein are pharmaceutically acceptable compositions comprising the nitrogenous heterocyclic compounds and the uses of the compositions in the treatment of human or animal tissue fibrosis, especially for human or animal renal interstitial fibrosis, glomerular sclerosis, liver fibrosis, pulmonary fibrosis, IPF, peritoneal fibrosis, myocardial fibrosis, dermatofibrosis, postsurgical adhesion, benign prostatic hyperplasia, skeletal muscle fibrosis, scleroderma, multiple sclerosis, pancreatic fibrosis, cirrhosis, myosarcoma, neurofibroma, pulmonary interstitial fibrosis, diabetic nephropathy, alzheimer disease or vascular fibrosis.

Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones

A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.

SIMPLE CONVERSION OF ARYL BROMIDES TO ARYLMETHYLPHOSPHONATES

Aryl bromides in tetrahydrofuran when combined with t-butyllithium and then with cuprous iodide and diethyl chloromethylphosphonate give diethyl arylmethylphosphonates.