- 1-hydroxy-1,1-bis(H-phosphinates): Synthesis, stability, and sorption properties
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A synthesis of 1-hydroxy-1,1-bis(H-phosphinates) from acylchlorides is described. Solid-state structures of two bis(phosphinates) determined by X-ray diffraction showed variations in the Pi-C distances. The compounds show negligible sorption on hydroxyapatite and an intermediate chemical stability in aqueous solution. The hydrolysis occurs in acidic as well as alkaline media. Hydrolysis rates of four derivatives show the lowest stability for aromatic derivatives as a result of the electron-withdrawing effect. Main products of hydrolysis are 1-hydroxy-(H-phosphinates) and phosphorous acid.
- David, Tomas,Kreckova, Pavlina,Kotek, Jan,Kubicek, Vojtech,Lukes, Ivan
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experimental part
p. 195 - 201
(2012/07/03)
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- Novel method for the synthesis of α-amino-α- hydroxyalkylphosphinic acids and bis(α-aminoalkyl)phosphinic acids: Nuclephilic addition of α-hydroxy-H-phosphinic acids to diimines
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We report here a novel and simple method for the synthesis of α-amino-α-hydroxyalkylphosphinic acids in good yields in two simple steps without any protection-deprotection steps. We have developed an efficient method for the synthesis of α-amino-α-hydroxyalkylphosphinic acids via the reaction of easily available α-hydroxyalkylphosphinic acids with diimines. Treatment of α-hydroxyalkylphosphinic acids with diimines in the presence of trimethylsilyl chloride (TMSCl) gives α-amino-α- hydroxyalkylphosphinic acids in good yields. The reaction gave a mixture of two diastereomeric forms of α-amino-α-hydroxyalkylphosphinic acids. The difference in solubility in organic solvents allowed us to readily separate the diastereoisomers. Georg Thieme Verlag Stuttgart · New York.
- Kaboudin, Babak,Haghighat, Hamideh,Alaie, Saied,Yokomatsu, Tsutomu
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supporting information; experimental part
p. 1965 - 1969
(2012/09/22)
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- Three component Kabachnik-Fields condensation leading to substituted aminomethane-P-hydroxymethylphosphonic acids as atool for screening of bacterial urease inhibitors
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Condensation of hydroxyalkane-H-phosphinic acids, formaldehyde and secondary amines has given entry to the synthesis of variously substituted aminomethane-P-hydroxymethylphosphinic acids. The proposed strategy allowed to perform a feasible synthesis of several molecules with designed biological activity towards bacterial urease - an enzyme which is a medicinally relevant molecular target. The inhibitory potency of compounds was validated using enzyme purified from Bacillus pasteurii. ARKAT-USA, Inc.
- Vassiliou, Stamatia,Grabowiecka, Agnieszka,Kosikowska, Paulina,Berlicki, Lukasz
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experimental part
p. 33 - 43
(2012/03/08)
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- Resolution of enantiomers of [α-hydroxy-(o-chlorophenyl)methyl] phosphinic acid via diastereomeric salt formation with enantiopure 1-phenylethylamines
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The resolution of racemic α-hydroxy-H-phosphinic acid with enantiopure 1-phenylethylamines via diastereomeric salt formation was investigated. X-Ray crystallographic analysis of the salt revealed that (R)-1-phenylethylamine to be efficient resolving agent for obtaining a single enantiomer of [α-hydroxy-(o-chlorophenyl)methyl]phosphinic acid. Resolving racemic α-hydroxy-H-phosphinic acid with (S)-2-phenylethylamine also gave access to (S)-α-hydroxyalkylphosphinic acid in good yield.
- Kaboudin, Babak,Alaie, Saied,Yokomatsu, Tsutomu
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experimental part
p. 1813 - 1816
(2012/01/05)
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- Asymmetrically substituted phosphinic acids
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The invention relates to asymmetrically substituted phosphinic acids of the formula (I) [in-line-formulae]R1R2C(OH)—P(═O)(OX)—C(OH)R3R4 ??(I)[/in-line-formulae] in which X is hydrogenR1, R2, R3, and R4 are identical or different and are hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl and/or alkaryl,with the proviso that the respective R1R2C(OH)— and —C(OH)R3R4 groups are always different, to a process for their preparation, and to their use.
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Page/Page column 21
(2008/12/08)
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- Phosphorylating power of red phosphorus towards aldehydes in basic and in acidic media
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The reactivity of red phosphorus towards aldehydes was investigated under basic and acidic media. It was demonstrated that the real phosphorylating agent involved in the reaction was phosphane (PH3) in basic media, and hypophosphorous acid (H3PO2) in acidic media. A convenient one- pot synthesis of (α-hydroxyalkyl)phosphinic acids from red phosphorus and aldehydes in basic media was realized under sonication. The same reaction under acidic media in the presence of hydriodic acid led to the corresponding phosphonic acids. The (α-hydroxyalkyl) phosphinic acids were readily prepared under sonication from hypophosphorous acid and aldehydes in the presence of catalytic amounts of hydrochloric acid. The mechanism of the addition reaction of PH3 to benzaldehyde was elucidated and shows the complexity of the reaction as a function of the experimental conditions.
- Albouy, Dominique,Etemad-Moghadam, Guita,Koenig, Max
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p. 861 - 868
(2007/10/03)
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