24630-67-9Relevant articles and documents
Methyl 4-toluenesulfonyloxymethylphosphonate, a new and versatile reagent for the convenient synthesis of phosphonate-containing compounds
Kó?iová, Ivana,To?ík, Zdeněk,Budě?ínsky, Milo?,?imák, Ond?ej,Liboska, Radek,Rejman, Dominik,Pa?es, Ond?ej,Rosenberg, Ivan
, p. 6745 - 6747 (2009)
A straightforward procedure leading to the new phosphonylating reagent, methyl 4-toluenesulfonyloxymethylphosphonate, requiring no chromatographic purification is described. This stable reagent works with the same efficiency as dimethyl and other dialkyl esters for the introduction of an O-phosphonomethyl moiety while, in contrast to dimethyl ester, it does not cause any unwanted methylation of sensitive functionalities. Its utility for the alkylation of protected nucleosides in high yield is exemplified.
Synthesis of dialkyl-hydroxymethylphosphonates in heterogeneous conditions
Jeanmaire, Thomas,Hervaud, Yves,Boutevin, Bernard
, p. 1137 - 1145 (2002)
This article describes the synthesis of a series of dialkyl-hydroxymethylphosphonates bearing various alkyl ester groups by the Pudovik reaction. The employed method uses anhydrous potassium carbonate as a catalyst in heterogeneous (solid/liquid) or mixed (solid/liquid and homogenous) conditions. All these syntheses are performed without any phase transfer agent and involve an anionic intermediate in a low polar or apolar solvent. These different products, obtained with high yields, have been characterised by 1H and 31P NMR and also by mass spectrometry. A study of fragmentation in the FAB ionisation process is given.
An efficient and simple strategy toward the synthesis of highly functionalized compounds
Jmai, Momtez,Efrit, Mohamed Lotfi,Dubreuil, Didier,Blot, Virginie,Lebreton, Jacques,M'rabet, Hédi
, p. 978 - 995 (2021/08/06)
The expedient syntheses of small libraries of ((β-ethoxycarbonyl, -cyano and -acetyl)propyloxy) methylphosphonate scaffolds bearing olefin, sulfanyl, or amine functions are described. All these new derivatives are readily produced from easily available starting reagents (aldehydes, electron-poor olefins, and dialkylphosphites) following a three steps reaction sequence of condensations, SN2′-type reaction and a conjugated thia- or aza-Michael 1,4-addition with aromatic and aliphatic thiol or amine nucleophiles.
Synthesis of a novel cyclopropyl phosphonate nucleotide as a phosphate mimic
Altenhofer, Erich F.,Fowler-Watters, Matthew,Joyce, Leo A.,Kumar, Pankaj,Lawler, Michael J.,Li, Zhen,Pei, Tao
supporting information, p. 6808 - 6811 (2021/07/13)
The inherentin vivoinstability of oligonucleotides presents one of many challenges in the development of RNAi-based therapeutics. Chemical modification to the 5′-terminus serves as an existing paradigm which can make phosphorylated antisense strands less prone to degradation by endogenous enzymes. It has been recently shown that installation of 5′-cyclopropyl phosphonate on the terminus of an oligonucleotide results in greater knockdown of a targeted protein when compared to its unmodified phosphate derivative. In this paper we report the synthesis of a 5′-modified uridine.
Melamine alkyl phosphate as well as preparation method and application thereof
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Paragraph 0028-0030, (2021/03/24)
The invention relates to melamine alkyl phosphate as well as a preparation method and application thereof, which mainly solves the problems that a common flame retardant generally cannot contain phosphorus and nitrogen elements at the same time and a preparation process of the flame retardant containing the phosphorus and nitrogen elements at the same time is complex in the prior art. Through providingmelamine alkyl phosphate, the preparation method comprises the following steps of adding methanol and 96% by mass of paraformaldehyde into a reaction vessel according to a molar ratio of (3-10):(1.5-5.0), adjusting the pH value to 9.5-11.5, depolymerizing paraformaldehyde, and adding dimethyl phosphite to react, thereby obtaining hydroxymethyl dimethyl phosphite, and reacting the partially etherified melamine resin with hydroxymethyl dimethyl phosphite according to the molar ratio of 1: (1-3) at the temperature of 80-100 DEG C, regulating the pH value to 8.5-9.5, and removing the solventto obtain the melamine alkyl phosphate and the application thereof, so that the problems are better solved, and the method can be applied to industrial application of polyurethane foam products.
Design, synthesis, and functional evaluation of a novel series of phosphonate-functionalized 1,2,3-triazoles as positive allosteric modulators of α7 nicotinic acetylcholine receptors
Nielsen, Beatriz Elizabeth,Stabile, Santiago,Vitale, Cristian,Bouzat, Cecilia
, p. 2688 - 2704 (2020/10/13)
The α7 nicotinic acetylcholine receptor is a pentameric ligand-gated ion channel widely distributed in the central nervous system, mainly in the hippocampus and cortex. The enhancement of its activity by positive allosteric modulators (PAMs) is a promising therapeutic strategy for cognitive deficits and neurodegenerative disorders. With the aim of developing novel scaffolds with PAM activity, we designed and synthesized a series of phosphonate-functionalized 1,4-disubstituted 1,2,3-triazoles using supported copper nanoparticles as the cycloaddition reaction catalyst and evaluated their activity on α7 receptors by single-channel and whole-cell recordings. We identified several triazole derivatives that displayed PAM activity, with the compound functionalized with the methyl phosphonate group being the most efficacious one. At the macroscopic level, α7 potentiation was evidenced as an increase of the maximal currents elicited by acetylcholine with minimal effects on desensitization, recapitulating the actions of type I PAMs. At the single-channel level, the active compounds did not affect channel amplitude but significantly increased the duration of channel openings and activation episodes. By using chimeric and mutant α7 receptors, we demonstrated that the new α7 PAMs share transmembrane structural determinants of potentiation with other chemically nonrelated PAMs. To gain further insight into the chemical basis of potentiation, we applied structure-activity relationship strategies involving modification of the chain length, inversion of substituent positions in the triazole ring, and changes in the aromatic nucleus. Our findings revealed that the phosphonate-functionalized 1,4-disubstituted 1,2,3-triazole is a novel pharmacophore for the development of therapeutic agents for neurological and neurodegenerative disorders associated with cholinergic dysfunction.
HERBICIDAL COMPOUNDS
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Page/Page column 77, (2020/08/22)
Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as herbicides.
Phosphonate-containing flame retardant and preparation method thereof
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Paragraph 0032; 0033, (2019/10/04)
The invention discloses a phosphonate-containing flame retardant and a preparation method thereof. The preparation method includes putting a reactor filled with methylol phosphinate diester, alkali and solvents into an ice water bath, adding an active-chlorine-containing compound, stirring reaction liquid for 1-24 hours of reaction at the temperature of 0-100 DEG C, and post-treating the reaction liquid to obtain a target product. The phosphonate-containing flame retardant has large molecular weight, is not liable to migrate, and can maintain flame retardant performance for a long time; the phosphonate-containing flame retardant has high molecular phosphorus content, contains multiple flame retardant structural units, and has high flame retardant efficiency and good flame retardant effect. The phosphonate-containing flame retardant can be applied to flame-retardant additives for polyurethane soft foam and other polymer materials, can serve as a flame retardant that is individually added to the polyurethane soft foam, and can be also used in combination with other flame retardants.
A synthetic paratoluene sulfonyl oxygen methyl phosphine acid ethyl ester
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Paragraph 0033-0034; 0047-0048; 0050-0051; 0053-0054; 0056, (2019/01/08)
The invention discloses a method for synthesizing paratoluene sulfonyl oxygen methyl phosphine acid ethyl ester method, 37% formaldehyde aqueous solution and the catalyst mixing, the dropping of the diethyl phosphite, the completion of the dropping, thermal insulation reaction 2 hours, to the reaction solution, the reaction solution into the solvent, to the toluene sulfonyl chloride, low temperature instillment base, the dropwise insulation 2 hours, extraction, washing, distillation, the surplus materials is high-purity paratoluene sulfonyl oxygen methyl phosphine acid diethyl ester. The method of the invention solve the existing craft in the low purity, yield is not high, the process is complicated, trouble in processing after, environmental pressure, is not suitable for industrial and the like.
The triazine ring-containing phosphorus-nitrogen-silicon composition and method of making the same
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Paragraph 0044-0046, (2017/03/22)
The invention relates to a reactive flame retardant and particularly relates to a triazine ring-containing phosphorus-nitrogen-silicon compound and a preparation method thereof. The preparation method comprises the following steps: S1, dissolving paraformaldehyde in methanol; adding a potassium carbonate solid; cooling the solution to 0 DEG C; stirring and adding dimethyl phosphate drop by drop; and S2, rising to room temperature, filtering out potassium carbonate after 1 hour, and decompressing and removing methanol from the filtrate to obtain colorless grease, namely an intermediate I. Compared with the prior art, the triazine ring-containing phosphorus-nitrogen-silicon compound provided by the invention has the beneficial effects that 1, three flame retardant elements phosphorus-nitrogen-silicon are integrated in one molecule, so that the heat stability, the charcoal forming property and the flame retardant synergic effect are improved; 2, the synthetic technological conditions are stable, the reaction process is easy to control and the production cost is low, and the compound has a good flame retardant effect under the condition of a small addition amount and can be used for flame retardant treatment of various fabrics.
