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Mémoire de Master : Utilisation des propriétés hôte-invité des calix[6]tris- acide pour la fonctionnalisation sélective, 2011. ,
76 (s, 3H, OCH 3 ), 3.77 (s, 6H, NCH 3 ), 3.81 (s, 3H10 (s, 2H, HAr N 3 ), 6.24 (s, 2H, HAr N 3 ), 6.28 (s, 2H, HAr tria, NCH 3 ), 4.10 (br m, 6H, ArCH ax ), 5.18 (d, J = 14.8 Hz, 2H, ImCH 2 ), 5.28 (d, J = 14.8 Hz, 2H, ImCH 2 ), 5.38 (s, 2H f : > 260°C (décomp.) ES-MS (DCM) m/z : 1511.7 (calc. 1511.6 pour [M C 4 NH 2 +Zn+ClO 4 ] + ). HRMS après démétallation m, pp.344120-344123 ,
ArCH eq ), 3.78 (s, 6H, OCH 3 ), 3.78 (s, 3H, NCH 3 ), 3.91 (s, 3H, NCH 3, Hz, vol.26721, issue.7, pp.5839-5842 ,
79 (s, 3H, OCH 3 ), 3.83 (s, 3H39 (s, 2H, 6H,ArCH ax ), 5.18 (d, J = 14.5 Hz, 2H, ImCH 2 ), 5.29 (d, J = 14.5 Hz 6.34 (s, 2H, HAr tria ), 6.91 (s, 1H, ImH), pp.78-82, 2003. ,
67 (s, 1H, H tria ) 13 C RMN (63 MHz, CD 3 CN, 300 K) ? (ppm) : 31, Hz, 1H HAr click ), 7.35 (d, J = 2.5 Hz, 4H, HAr t?Bu ), 7.4 (m, 4H, ImH + HAr click ), p.9731 ,
54 (d, J = 15.9 Hz, 2H, ArCH ax ), 3.65 (d, J = 15.8 Hz, 4H, ArCH ax ), 3.59 (s, 6H, OCH 3 ), 3.68 (s, 3H, OCH 3 ), 3.80 (s, 6H, NCH 3 ), 3.81 (s, 3H, NCH 3 ), 4.10 (m, 6H, ArCH eq ), 5.33 (sl, 6H, HAr N 3 ), 6.73 (s, 2H, HAr tria ), 6.92 (d, J = 1.6 Hz, pp.48-51 ,
75 (s, 2H, HAr N 3 ), 5.84 (s, 2H, HAr N 3 ), 6.47 (s, 1H, ImH), 6.54 (s, 2H, ImH), 6.58 (s, 2H, 2H, ImCH 2 ), 4.96 (s, 4H, ImCH 2 ), 5.06 (d, J = 13 Hz HAr tria ), 7.03 (s, 1H, ImH), p.8283035 ,
76 (s, 3H, OCH 3 ), 4.08 (sl, 6H, ArCH ax ), 5.05 (s, 4H81 (s, 2H86 (s, 2H, 6.89 (d, J = 1.6 Hz, 1H, ImH), 6.92 (d, J = 1.6 Hz, 2H, ImH), 7.36 (s, 1H, H tria ), 7.38 (s, 2H, HAr t?Bu ), 7.39 (d, J = 2.2 Hz ), 3.65 (s, 3H, NCH 3 ), 3.76 (s, 3H, OCH 3 ), 4.07 (ml, 6H, ArCH eq ), 4.12 (d, J = 6.3 Hz, CH 2 NHBoc pour [M ArCH 2 NHBoc +H] + ). IR (ATR) ? (cm ?1 ) : 873.0, pp.50-53, 1073. ,
65 (s, 12H, OCH 3 + NCH 3 ), 3.66 (s, 3H, NCH 3 ), 3.76 (s, 3H, OCH 3 ), 4.08 (sl, 6H, ArCH ax ), 5.05 (s, 4H, ImCH 2 ), 5.08 (s, 2H, ImCH 2 ), 5.81 (s, 2H86 (s, 2H, HAr N 3 ), 6.33 (s, 2H, HAr tria ), RMN (500 MHz, CD 3 CN, 300 K) ? (ppm) : 1.35 (s, 18H 7.38 (s, 2H, HAr t?Bu ), 7.39 (d, J = 2.2 Hz, 2H,HAr t?Bu ), 7.41 (d, J = 2.2 Hz, 2H,HAr t?Bu ), pp.3839399250-3 ,
·6H 2 O (106 mg, 0.285 mmol, 1.0 eq) est ajouté à une solution de ligand M ArCH 2 NHBoc (422 mg, 0.285 mmol) dans du THF distillé in dry THF (15 mL) La solution est agitée 1 heure à TA puis de l'éther (150 mL) est ajouté, entrainant la précipitation d'un solide blanc. Après filtration et séchage sous vide, p.99 ,
58 (s, 3H, OCH 3 ), 3.67 (s, 3H, OCH 3 ), 3.74 (s, 6H, OCH 3 +NCH 3 ), 3.77 (s, 3H, NCH 3 ), 3.81 (s, 3H09 (s, 1H, HAr N 3 ), 6.18 (s, 1H, HAr N 3 ), 6.19 (s, 1H, HAr tria ), 6.27 (s, 1H, HAr tria ), 6.38 (s, 1H, HAr tria ), 6.82 (s, 1H, HAr tria, RMN (500 MHz, CD 3 CN, 300 K) ? (ppm) : -1.05 NCH 3 ), 4.07 (ml, 6H, ArCH ax ), 4.13 (t, J = 5.2 Hz, 2H, ArCH 2 NHBoc), 5.16 (d, J = 10.4 Hz, ImCH 2 ), 5.19 (d, J = 10.4 Hz, 1H, ImCH 2 ), 5.28 (ml, 2H, ImCH 2 ), 5.38 (sl, 2H, ImCH 2 ), 5.72 (sl, J = 2.5 Hz, 2H, HAr t?Bu ), 7.38 (s, 1H, H tria BnNHBoc ), (d, J = 2.5 Hz, 1H, HAr t?Bu ), 7.40 (d, J = 2.5 Hz, 1H, HAr t?Bu ), 7.40 (d, J = 2.5 Hz,1H, HAr t?Bu ), 7.42 (d, J = 2.5 Hz, 1H, HAr t?Bu ), pp.983234-983235 ,
HRMS après démétallation m ,
ClO 4 ) 2 (52 mg, 32 µmol, 1.0 eq) est mis en suspension dans une solution de 3-éthynylbenzylamine (13 mg ,
ArCH ax ), 3.76 (d, J = 15.2 Hz, 1H, ArCH eq, p.75 ,
49 (s, 1H01 (s, 1H, HAr N 3 ), 6.35 (s, 1H, HAr tria Bn ), 6.49 (s, 1H, HAr tria Bn ), 6.55 (s, 1H, HAr tria C 3, 1H, ImCH 2 ), 5.67 (d, J = 15.1 Hz, 1H, ImCH 2 ),5.87 (t, J = 8.1 Hz, 1H, b), ImH), 7.24 (s, 1H, HAr t?Bu ), 7.24 (s, 1H, HAr tria C 3 ), pp.5-4134 ,
ES-MS (MeOH après démétallation) ,
75 (d, J = 15.2 Hz, 1H, ArCH eq ), 3.77 (s, 3H, NCH 3 ), 3.78 (s, 3H, NCH 3 ), 3.80 (s, 3H, OCH 3 ), 3.93 (s, 3H, NCH 3 ), 4.09 (d, J = 15.2 Hz, 1H, ArCH ax ), 4.21 (d, J = 15 ,
ArCH ax ), 4.41 (d, J = 15.2 Hz, 1H, ArCH ax ), 4.63 (d, J = 8.1 Hz, 4.31 (d, J = 15.2 Hz, 1H, pp.30-35 ,
46 (s, 1H, pp.58-63 ,
99 (s, 1H51 (s, 1H, HAr tria Bn ), 6.56 (s, 1H, HAr tria C 4 OH ), 1H, ImH), 7.02 (s, 1H, ImH), 7.24 (s, 1H, HAr t?Bu ), 7.30 (s, 1H, HAr tria C 4 ), 7.34 (s, 1H, HAr t?Bu ), pp.5-773095, 2000. ,
69 (s, 1H78 (s, 1H, H tria Bn ) 13 C RMN (125 MHz, CD 3 CN, 300 K) ? (ppm) : 25.2, 25, p.pour pour ,
40 (d, J = 2.3 Hz, HAr tria ), 7.24 (s, 1H, H tria ), HAr tBu ). ESI-MS, CH 3 OH m, pp.32-1356 ,
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