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  • Organic Chemistry  (2)
  • 31P arsenophosphonolipid  (1)
  • Wiley-Blackwell  (3)
  • 1
    Digitale Medien
    Digitale Medien
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 1 (1987), S. 403-412 
    ISSN: 0268-2605
    Schlagwort(e): Trimethyl-2-hydroxyethylarsonium salts ; arsenocholine ; trimethyl-2-haloethylarsonium bromide ; trimethyl-2-acetoxyethylarsonium bromide ; acetylarsenocholine ; trimethyl-2-(dihydrogen phosphato)ethylarsonium bromide ; 1H and 13C NMR spectra ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Trimethyl-2-X-ethylarsonium salts (X=OH, Cl, Br, CH3COO; anion=Br) and trimethyl-2-diethoxyethylarsonium bromide were prepared from trimethylarsine and the appropriate organic bromides in sealed tubes at elevated temperatures or by refluxing the neat reagents. The yields ranged from 33 to 85%. Anion exchange reactions produced the arsonium iodides, nitrates, acetates, tosylates, tetraphenylborates, picrates, hydroxides, and carbonates. Arsenocholine bromide (X=OH) was phosphorylated with concentrated phosphoric acid. The product was isolated as the barium salt. Treatment of the barium salt with sulfuric acid yielded trimethyl-2-(dihydrogen phosphato)ethylarsonium bromide. These substances were synthesized to serve as precursors for arsenic- containing phospholipids and as standards for the chromatographic identification of arsenocholines. The synthesized compounds were characterized by elemental analyses and 1H and 13C NMR spectroscopy. The shifts of the arsenic compounds were compared with those of the corresponding nitrogen compounds and found to be sufficiently different to be used for the identification of these compounds in their mixtures.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    Standort Signatur Erwartet Verfügbarkeit
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  • 2
    ISSN: 0749-1581
    Schlagwort(e): Arsenolipid ; 2D NMR ; 1H and 13C NMR ; 31P arsenophosphonolipid ; Chemistry ; Analytical Chemistry and Spectroscopy
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The 1H (500 MHz), 13C (300 MHz) and 31P (202 MHz) NMR spectra of rac-2,3-bis(palmitoyloxy)propyl(2-trimethylarsonioethyl)phosphonate were recorded in CDCl3 (3 M) solution. Homonuclear 1H-1H and heteronuclear 13C-1H chemical shift correlation experiments (COSY) were performed. All resonances were assigned. The shifts of the arsenic-containing phosphonolipid were compared with the shifts of the N-containing phospholipids. The most significant shift differences were found for the groups directly bonded to arsenic. Spectral evidence was indicative of free rotation about the —CH2 —CH2 —bond in the arsenocholine fragment.
    Zusätzliches Material: 5 Ill.
    Materialart: Digitale Medien
    Standort Signatur Erwartet Verfügbarkeit
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  • 3
    Digitale Medien
    Digitale Medien
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 4 (1990), S. 103-109 
    ISSN: 0268-2605
    Schlagwort(e): Arsenic-containing lipids ; 2-trimethylarsonioethylphosphonic acid bromide ; 1,2-bis(palmitoyloxy)-3-propyl 2-trimethylarsonioethylphosphonate ; arsenic-containing phosphonolipid ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Arsenic analogs of lecithins (i.e. with replacement of nitrogen by arsenic in the choline group) are probably trace constituents of phospholipids in many organisms. Attempts to synthesize 1,2-bis(palmitoyloxy)-3-propyl 2-trimethylarsonioethyl phosphate (arsenolecithin) according to wellestablished procedures for the synthesis of the corresponding nitrogen compound failed. However, 1,2-bis(palmitoyloxy)-3-propyl 2-trimethylarsonioethylphosphonate, an arsenic-containing phosphonolipid, was obtained in 16% yield by reacting 1,2-bis(palmitoyloxy)-3-iodopropane with silver 2-trimethylarsonioethylphosphonate in isopropanol. The precursors to the arsenic-containing phosphonolipid were obtained by quaternization of trimethylarsine with diethyl 2-bromoethylphosphonate, hydrolysis of the resulting product with concentrated hydrochloric acid, and reaction of the phosphonic acid with silver oxide to give silver 2-trimethylarsonioethylphosphonate. Quaternization and hydrolysis proceeded almost quantitatively. The silver phosphonate was not isolated but was used in situ.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    Standort Signatur Erwartet Verfügbarkeit
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