69404-44-0Relevant academic research and scientific papers
Intensified Continuous Flow Michaelis-Arbuzov Rearrangement toward Alkyl Phosphonates
Monbaliu, Jean-Christophe M.,Toupy, Thomas
supporting information, p. 467 - 478 (2022/02/25)
Herein is described the development of an intensified continuous flow process for the preparation of a library of alkyl phosphonates through a Michaelis-Arbuzov rearrangement. A careful process optimization and thorough analysis of the competitive reactions led to a very attractive protocol with unprecedented productivities (up to 4.97 kg of material per day) and a low environmental footprint with the absence of solvent, additives, catalysts, and waste. In-line low-field 31P NMR monitoring was conveniently implemented for rapid optimization and process monitoring. Two key alkyl phosphonate intermediates were also assessed for the unprecedented diazene dicarboxylate-mediated electrophilic amination under continuous flow conditions toward the α-aminophosphonic acid derivatives of Pphenylalanine and Palanine, bioisosters of the natural amino acids phenylalanine and alanine, respectively.
Nickel-catalyzed coupling of R2P(O)Me (R = aryl or alkoxy) with (hetero)arylmethyl alcohols
Li, Wei-Ze,Wang, Zhong-Xia
, p. 2233 - 2242 (2021/03/24)
α-Alkylation of methyldiarylphosphine oxides with (hetero)arylmethyl alcohols was performed under nickel catalysis. Various arylmethyl and heteroarylmethyl alcohols can be used in this transformation. A series of methyldiarylphosphine oxides were alkylated with 30-90% yields. Functional groups on the aromatic rings of methyldiarylphosphine oxides or arylmethyl alcohols including OMe, NMe2, SMe, CF3, Cl, and F groups can be tolerated. The conditions are also suitable for the α-alkylation reaction of dialkyl methylphosphonates.
Recognition characteristics of an adaptive vesicular assembly of amphiphilic baskets for selective detection and mitigation of toxic nerve agents
Chen, Shigui,Ruan, Yian,Brown, Jason D.,Hadad, Christopher M.,Badji, Jovica D.
supporting information, p. 17337 - 17342 (2015/02/02)
We used isothermal titration calorimetry to investigate the affinity of basket 1 (470 ?3) for trapping variously sized and shaped organophosphonates (OPs) 2-12 (137-244 ?3) in water at 298.0 K. The encapsulation is, in each case, dri
Palladium-catalyzed hydrophosphonylation of alkenes with dialkyl H-phosphonates
Candy, Mathieu,Rousseaux, Sophie A. L.,Sanroman, Alberto Cirugeda,Szymczyk, Monika,Kafarski, Pawel,Leclerc, Eric,Vrancken, Emmanuel,Campagne, Jean-Marc
supporting information, p. 2703 - 2708 (2014/09/29)
The palladium-catalyzed hydrophosphonylation of alkenes with previously unreactive acyclic dialkyl H-phosphonates has been developed. A catalyst system based on palladium/DavePhos or palladium/SPhos enables the transformation of various alkenes to phospho
Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity
McKittrick, Brian A.,Ma, Ke,Huie, Keith,Yumibe, Nathan,Davis Jr., Harry,Clader, John W.,Czarniecki, Michael,McPhail, Andrew T.
, p. 752 - 759 (2007/10/03)
The C3 phenylpropyl side chain N-phenylazetidinones related to SCH 56524 was modified by replacing the hydroxymethylene with various isoelectronic or isosteric groups. Modifications at the 3' position led to less-active compounds; however, modifications a
PHOSPHONATE AND PHOSPHONAMIDE ENDOPEPTIDASE INHIBITORS
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, (2008/06/13)
Compounds of the formula STR1 wherein Y is O or NH and X is STR2 will inhibit the action of neutral endopeptidase. As a result, such compounds produce diuresis, natriuresis, and lower blood pressure as well as being useful in the treatment of congestive heart failure, relieving pain, and diarrhea when administered to a mammalian host.
