64050-53-9

Usage

InChI:InChI=1/C15H19O4P/c1-3-17-20(16,18-4-2)19-12-14-10-7-9-13-8-5-6-11-15(13)14/h5-11H,3-4,12H2,1-2H3

Upstream product

• 4780-79-4 1-naphthalene methanol 
• 814-49-3 diethyl chlorophosphate 
• 66-77-3 1-naphthaldehyde 
• 762-04-9 phosphonic acid diethyl ester 
• 1090-21-7 diethyl hydroxy(naphth-1-yl)methylphosphonate 

Downstream Products

• 5903-23-1 1-(methoxymethyl)naphthalene 
• 90-12-0 1-Methylnaphthalene 
• 19351-91-8 N-(naphthalene-1-ylmethyl)acetamide 
• 611-45-0 1-Benzyl-naphthalene 
• 607-50-1 1,1'-dinaphthylmethane 

Relevant academic research and scientific papers

Formation of new phosphates from aldehydes by a DBU-catalysed phospha-brook rearrangement in a polar solvent

Addition of dialkylphosphites to aromatic aldehydes (Pudovik reaction) by treatment with a base results in two different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate. Georg Thieme Verlag Stuttgart.

BuLi-triggered phospha-Brook rearrangement: Efficient synthesis of organophosphates from ketones and aldehydes

A variety of organophosphates are synthesized from n-BuLi-triggered, (additional) solvent-free reactions of diethyl phosphite with both activated/unactivated ketones and aldehydes preferably at room temperature via phospha-Brook rearrangement. We could successfully synthesize the naphthylic/allylic phosphates using this approach.

Synthesis of diarylmethanes through palladium-catalyzed coupling of benzylic phosphates with arylsilanes

An efficient approach to the benzylation of arenes has been developed. The reactions described provide straightforward access to diarylmethanes through Pd-catalyzed coupling of benzylic phosphates with arylsilanes in good to excellent yields. The reaction tolerates a wide range of functionalities such as halide, alkoxyl, and nitro groups.

Inhibition of purple acid phosphatase with α-alkoxynaphthylmethylphosphonic acids

Purple acid phosphatases (PAPs) are binuclear hydrolases that catalyse the hydrolysis of a range of phosphorylated substrates. Human PAP is a major histochemical marker for the diagnosis of osteoporosis. In patients suffering from this disorder, PAP activity contributes to increased bone resorption and, therefore, human PAP is a key target for the development of anti-osteoporotic drugs. This manuscript describes the design and synthesis of derivatives of 1-naphthylmethylphosphonic acids as inhibitors of PAP. The Ki values of these compounds are as low as 4 μM, the lowest reported to date for a PAP inhibitor.

Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids

(Chemical Equation Presented) Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids was investigated. Optimum conditions employed the simple catalytic system of palladium(II) acetate (1 mol %) and triphenylphosphine (4 mol %) with either potassium phosphate or potassium carbonate as the base and toluene as the solvent at 90°C. Using the developed conditions, a series of structurally diverse diarylmethanes were prepared.

A simple, general and improved procedure for phosphorylation of alcohols catalyzed by indium(III) chloride

A general and efficient procedure has been developed for the preparation of dialkyl phosphate esters by indium(III) chloride catalyzed phosphoryl transfer from diethyl and diphenyl chlorophosphate to a variety of alcohols and phenols in THF in presence of triethylamine.