67696-25-7Relevant academic research and scientific papers
Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes
Tang, Xiaoping,Chapman, Charlotte,Whiting, Matthew,Denton, Ross
supporting information, p. 7340 - 7343 (2014/07/07)
The development of the first redox-free protocol for the Mitsunobu reaction is described. This has been achieved by exploiting triphenylphosphine oxide-the unwanted by-product in the conventional Mitsunobu reaction-as the precursor to the active P(v) coupling reagent. Multinuclear NMR studies are consistent with hydroxyl activation via an alkoxyphosphonium salt.
The structure?activity relationship of the 3-Oxy site in the anticonvulsant (R)- N -benzyl 2-acetamido-3-methoxypropionamide
Morieux, Pierre,Salomé, Christophe,Park, Ki Duk,Stables, James P.,Kohn, Harold
supporting information; experimental part, p. 5716 - 5726 (2010/10/03)
Lacosamide ((R)-N-benzyl 2-acetamido-3-methoxypropionamide, (R)-1) is a low molecular weight anticonvulsant recently introduced in the United States and Europe for adjuvant treatment of partial-onset seizures in adults. In this study, we define the structure?activity relationship (SAR) for the compound's 3-oxy site. Placement of small nonpolar, nonbulky substituents at the 3-oxy site provided compounds with pronounced seizure protection in the maximal electroshock (MES) seizure test with activities similar to (R)-1. The anticonvulsant activity loss that accompanied introduction of larger moieties at the 3-oxy site in (R)-1 was offset, in part, by including unsaturated groups at this position. Our findings were similar to a recently reported SAR study of the 4?-benzylamide site in (R)-1 (J. Med. Chem. 2010, 53, 1288 ?1305). Together, these results indicate that both the 3-oxy and 4?-benzylamide positions in (R)-1 can accommodate nonbulky, hydrophobic groups and still retain pronounced anticonvulsant activities in rodents in the MES seizure model.
THE THERMOLYTIC DECOMPOSITION OF ACYCLIC PHOSPHORANES
Lowther, Nicholas,Crook, Polly,Hall, C. Dennis
, p. 195 - 204 (2007/10/02)
The thermolytic decomposition of acyclic phosphoranes, ArnP(OCH2CF3)5-n in aprotic media has been shown by kinetic studies to proceed via rate-limiting ionization of the phosphoranes.Activation parameters, deuterium isotope effects, solvent effects and ρ-values (for n = 3 and n = 1) support this concept which is consistent with the observed rate-sequence of n = 3> n = 2 > n = 1 > n = 0.Key words: Phosphoranes, thermolysis, kinetics, mechanism.
CONCERNING THE FORMATION, HYDROLYSIS AND THERMOLYSIS OF ACYCLIC PHOSPHORANES
Lowther, Nicholas,Crook, Polly,Hall, Dennis
, p. 405 - 408 (2007/10/02)
Kinetic data on the formation, hydrolysis and thermolysis of acyclic phosphoranes is reported and the mechanism of each reaction is discussed.
The Mechanism of the Mitsunobu Reaction. II. Dialkoxytriphenylphosphoranes
Itzstein, Mark von,Jenkins, Ian D.
, p. 557 - 563 (2007/10/02)
31P n.m.r. studies indicate that, in the Mitsunobu reaction, alcohols (ROH) react with triphenylphosphine (Ph3P) and dialkyl azodicarboxylates to produce phosphoranes of the type Ph3P(OR)2.Mixtures of alcohols produce, in addition, mixed phosphoranes, Ph3
Novel Synthetic Reactions Using Bis(2,2,2-trifluoroethoxy)triphenylphosphorane
Kubota, Toshio,Miyashita, Satoshi,Kitazume, Tomoya,Ishikawa, Nobuo
, p. 5052 - 5057 (2007/10/02)
Alkoxy-or (acyloxy)(2,2,2-trifluoroethoxy)triphenylphosphoranes which were prepared in situ by the ligand exchange of bis(2,2,2-trifluoroethoxy)triphenylphosphorane with alcohols or carboxylic acids were found to behave as potential alkylating or acylating reagents for the preparation of a variety of esters, amides, sulfides, and ketones.
