30148-50-6Relevant articles and documents
Phosphinic acid analogues of thiaproline and the related heterocyclic aminophosphinic acids
Hatam,Martens
, p. 2553 - 2559 (1995)
Bis(trimethylsilyl) phosphonite adds in a 1,2 fashion to the C = N bond in 3-thiazolines 3a-d to give after hydrolysis phosphinic acids 5a-d. Starting from 3-oxazines, the corresponding 6a,b phosphinic acids 7a,b were obtained.
Synthesis of Phosphine Analog of Glutamylglcine
Ragulin, V. V.
, p. 1823 - 1824 (2001)
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One-pot synthesis of α-amino phosphinic acids
Ragulin
, p. 142 - 143 (2004)
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Complexes of divalent transition metal ions with bis(aminomethyl)phosphinic acid in aqueous solution and in the solid state
Kubicek, Vojtech,Vojtisek, Pavel,Rudovsky, Jakub,Hermann, Petr,Lukes, Ivan
, p. 3927 - 3938 (2003)
Bis(aminomethyl)phosphinic acid, (NH2CH2)2PO2H (HL), was synthesized using a new procedure. Its coordination ability towards CO(II)/(III), Ni(II), Cu(II) and Zn(II) was studied both in solution and in the solid state. Because of the presence of two nitrogen atoms the ligand exhibits a higher overall basicity than common (aminoalkyl)phosphinic acids. Consequently, the values of the determined stability constants are comparable with those found for (aminoalkyl)phosphonic acids. NMR titrations of Zn(II) point to the interaction of phosphinate with the metal ion in a strong acid solution. The X-ray structures show several coordination modes in the solid state. All-trans-[MCl2(H2L-O)2 (H2O)2]Cl2, where M(II) are Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Ca(II), and Cd(II), crystallized from acid solutions. The central ion is octahedrally coordinated with two phosphinate oxygen atoms, two molecules of water and two chlorides in all-trans arrangement. Amine groups are protonated and non-coordinated. Participation of the donor groups in crystals isolated from neutral solutions depends on the metal ion. All donor atoms are coordinated in monomeric fac-N,N,O-trans-O,O'-[Co(L-N,N,O)2]+. On the other hand, in the zinc(II) complex, two phosphinate oxygen atoms and two amine nitrogen atoms (trans to each other) of two different ligand molecules are coordinated in an equatorial plane and two amino groups of the two other ligand molecules are bound in axial positions. Thus, each molecule of the amino acid forms a five-membered N,O-chelate to one zinc(II) ion and the other amino group is bound to the neighbouring ion creating an infinite chain. Nickel(II) forms a trans-O,O′-[Ni(H2O)2-(L-N,N)2] complex in which the metal ion is chelated by four amine nitrogen atoms forming two six-membered chelates in an equatorial plane and the octahedron is completed with two water molecules at the apical positions. The phosphinate group is not coordinated. The above results point to a relatively low coordination ability of the phosphinate group; however, due to its low pKA, it is able to bind metal ions at lower pH than other coordinating groups do.
Reactions of Unsaturated Ketones with Bis(trimethylsilyl) Hypophosphite
Tatarinov,Kundina,Dobrynin,Mironov
, p. 90 - 95 (2018)
Bis(trimethylsilyl) hypophosphite reacts with unsaturated ketones (methyl vinyl ketone and mesityl oxide) to give, depending on the reaction conditions, 1: 1 or 1: 2 adducts after hydrolysis. It was found that the intramolecular cyclization of the 1: 2 reaction product with mesityl oxide, trimethylsilyl bis(2-methyl-4- oxopentan-2-yl)phosphinate, yields, after hydrolysis, a phosphorinane with exocyclic carbonyl and hydroxyl groups.
Synthesis of a bifunctional monophosphinate DOTA derivative having a free carboxylate group in the phosphorus side chain
Rezanka, Pavel,Kubicek, Vojtech,Hermann, Petr,Lukes, Ivan
, p. 1431 - 1435 (2008)
A new bifunctional cyclen-based ligand, 3-[hydroxy({4,7,10-tris[(tert- butoxycarbonyl)methyl]-1,4,7,10-tetraazacyclododecan-1-yl}methyl)phosphoryl] propanoic acid, was synthesized by alkylation of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate (t-Bu3DO3A) by ethyl 3-{ethoxy[(mesyloxy)methyl]phosphoryl}propanoate [MsOCH2P(O)(OEt) CH2CH2CO2Et]. The ethyl carboxylate group in the side chain was selectively deprotected to obtain the esterified bifunctional ligand. More efficient syntheses of some phosphinopropanoic acid derivatives were devised and the phosphorus alkylation reagent was prepared starting from hypophosphorus acid or its salt. Georg Thieme Verlag Stuttgart.
Nucleoside H-boranophosphonates: A new class of boron-containing nucleotide analogues
Higashida, Renpei,Oka, Natsuhisa,Kawanaka, Toshihide,Wada, Takeshi
, p. 2466 - 2468 (2009)
A study on the synthesis of nucleoside H-boranophosphonates, a new class of nucleotide analogues having a P→BH3 and a P-H group, via condensation of the corresponding nucleosides with H-boranophosphonate derivatives is described. The Royal Soci
Mechanism of Phosphorus-Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids
Dmitriev, Maxim E.,Golovash, Sofia R.,Borodachev, Alexei V.,Ragulin, Valery V.
supporting information, p. 593 - 600 (2021/01/14)
An unusual greater reactivity of phosphonous propionic acids was found in comparison with phosphonous propionic esters in carbamate version of Kabachnik-Fields reaction. Compounds of tricoordinated phosphorus generated in situ during the amidoalkylation o
A Carbodiimide-Mediated P-C Bond-Forming Reaction: Mild Amidoalkylation of P-Nucleophiles by Boc-Aminals
Kokkala, Paraskevi,Rajeshkumar, Thayalan,Mpakali, Anastasia,Stratikos, Efstratios,Vogiatzis, Konstantinos D.,Georgiadis, Dimitris
supporting information, p. 1726 - 1730 (2021/03/08)
The first example of a carbodiimide-mediated P-C bond-forming reaction is described. The reaction involves activation of β-carboxyethylphosphinic acids and subsequent reaction with Boc-aminals using acid-catalysis. Mechanistic experiments using 31P NMR spectroscopy and DFT calculations support the contribution of unusually reactive cyclic phosphinic/carboxylic mixed anhydrides in a reaction pathway involving ion-pair "swapping". The utility of this protocol is highlighted by the direct synthesis of Boc-protected phosphinic dipeptides, as precursors to potent Zn-aminopeptidase inhibitors.
