Synthese spinmarkierter Alkylamine als potentielle Enzymeffektoren

Synthesis, physicochemical properties and antimicrobial activity of mono-/dinitroxyl amides

“…-1-oxide (8). Modifying the described procedure, 20 nitroxide 8 was prepared by reaction of 4-amino-TEMPO 1 (171 mg, 1 mmol) and Et 3 N (203 mg, 280 μL, 2 mmol) with (CF 3 CO) 2 O (420 mg, 282 μL, 2 mmol) in anhydrous DCM (4 mL). After the reaction was complete (6 h, TLC control), the mixture was diluted with DCM (15 mL), washed with 1 N HCl (15 mL), saturated aq.…”

Enhancement of the Oxidizing Power of an Oxoammonium Salt by Electronic Modification of a Distal Group

“…The mixture was stirred for an additional 1 h and then filtered through a Büchner funnel. The resulting off-white solid was rinsed with a 200 mL portion of diethyl ether and then dried in a vacuum oven at 120 °C to afford 180.7 g (99% yield) of the title compound as a white powdered solid: mp 256 °C (dec) [lit . mp 220 °C (dec)]; 1 H NMR (400 MHz, CD 3 CN) δ 1.43 (s, 6H), 1.50 (s, 6H), 1.75 (t, J = 13.0 Hz, 2H), 1.96 (dd, J = 3.8 Hz, J = 13.0 Hz, 2H), 4.23–4.33 (m, 1H), 7.74 (d, J = 5.3 Hz, 1H); 13 C NMR (100 MHz, CD 3 CN) δ 25.0, 30.5, 40.7, 42.8, 58.1, 117.0 (q, J C–F = 287.6 Hz), 118.1 (q, J C–F = 294.6 Hz), 157.4 (q, J C–F = 36.7 Hz), 161.2 (q, J C–F = 33.5 Hz); 19 F NMR (376 MHz, CD 3 CN) δ −74.2 (3F), −74.7 (3F); HRMS (DART-TOF) m / z calcd for C 11 H 20 F 3 N 2 O [M – CF 3 COO] + 253.1528, found 253.1522.…”

“…The reaction mixture was stirred vigorously for 12 h at room temperature, an additional 120 mL (1.1 mol) of the hydrogen peroxide solution was then added dropwise over a period of 2 h, and the mixture was then stirred at room temperature for an additional 24 h. The orange reaction mixture was cooled to −10 °C in an ice/salt bath and filtered through a large Büchner funnel to give 107.5 g (83%) of the title compound as an orange solid. An analytical sample, prepared by recrystallization from EtOAc, afforded a glistening, orange-red, crystalline solid that displayed the following properties: mp 149.6–151.8 °C (lit . mp 149–152 °C); HRMS (DART-TOF) m / z calcd for C 11 H 18 F 3 N 2 O 2 [M] + 267.1320, found 267.1335.…”

“…The resulting off-white solid was rinsed with a 200 mL portion of diethyl ether and then dried in a vacuum oven at 120 °C to afford 180.7 g (99% yield) of the title compound as a white powdered solid: mp 256 °C (dec) [lit. 17 3) of substituted benzyl alcohols by 1 and 5; k BA = rate constant for oxidation of benzyl alcohol, and k X = rate constant for oxidation of substituted benzyl alcohol. 4).…”

“…An analytical sample, prepared by recrystallization from EtOAc, afforded a glistening, orange-red, crystalline solid that displayed the following properties: mp 149.6− 151.8 °C (lit. 17 2,2,6,6-Tetramethyl-4-(2,2,2-trifluoroacetamido)-1-oxopiperidinium Tetrafluoroborate (5). To a 250 mL beaker equipped with a magnetic stir bar were added 20.0 g (74.9 mmol) of 2,2,6,6tetramethyl-4-(2,2,2-trifluoroacetamido)piperidine-1-oxyl (4) and 50 mL of deionized water.…”