Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10.3 Cyclisierungsedukte 245
1 H-NMR δ [ppm]:
(300 MHz) Aceton-d6
3.67 (s, 3H, CH3, N-CH3); 3.71 (s, 3H, CH3, 1'''-H); 6.46 (d,
3 J=15.82, 1H, CH, 2''-H ((E)-Isomer)); 7.32 (ddd, 3 J=7.91,
3 J=8.29, 4 J=1.13, 1H, CH, 6-H); 7.40 (ddd, 3 J=7.16,
3 J=8.29, 4 J=1.13, 1H, CH, 5-H); 7.56 (d, 3 J=16.20, 1H, CH,
3''-H ((E)-Isomer)); 7.64 (d, 3 J=7.91, 1H, CH, 7-H); 7.78 (d,
3 J=8.67, 2H, 2xCH, 3'-H, 5'-H); 8.02 (d, 3 J=7.54, 1H, CH, 4-
H); 8.09 (d, 3 J=8.29, 2H, 2xCH, 2'-H, 6'-H)
13
C-NMR δ [ppm]: 31.0 (CH3, N-CH3); 50.6 (CH3, C-1'''); 110.0 (Cq, C-3);
(75 MHz)
110.9 (CH, C-2''); 112.5 (Cq, C-4'); 112.7 (CH, C-7); 118.2
Aceton-d6 / DMSO-d6 (Cq, C-1 lV ); 120.4 (CH, C-4); 121.9 (CH, C-5); 123.4 (CH,
C-6); 125.0 (Cq, C-3a); 131.9 (2xCH, C-2' und C-6'); 132.5
(2xCH, C-3' und C-5'); 134.6 (Cq, C-1'); 137.5 (CH, C-3'');
138.2 (Cq, C-7a); 143.1 (Cq, C-2); 167.5 (Cq, C-1'')
EI-MS (70 eV); m/z (%) 316.2 (_, 100.00), 285.1 (49.27), 255.9 (88.41), 241.9
(50.73), 214.0 (5.80), 127.8 (17.90)
Elementaranalyse (%): Ber.: C: 75.93 H: 5.10 N: 8.85
Gef.: C: 75.78 H: 5.16 N: 8.76
UV/VIS [nm]: lgε
CH3OH
λmax: 301.5 (4.4353), λ1: 350.0 (4.3304), λ2: 262.5 (4.2588)
IR (KBr); ö [cm -1 ] 3046 (w) 2944 (w) 2912 (w) 2885 (w) 2836 (w)
2232 (m) 1687 (s) 1605 (s) 1573 (m) 1521 (m)
1489 (m) 1460 (s) 1432 (s) 1404 (m) 1365 (s)
1342 (m) 1308 (s) 1290 (s) 1268 (s) 1215 (s)
1192 (s) 1176 (s) 1137 (s) 1114 (m) 1067 (s)
1036 (m) 1014 (m) 965 (m) 932 (w) 862 (s)
843 (s) 829 (m) 816 (m) 763 (w) 752 (m)
741 (m) 730 (s) 664 (w)
10.3.2.32 (E)-3-[2-(4-Methoxy-2-methylphenyl)-1-methyl-1H-indol-3-yl]-acrylsäure-
methylester (93)
6
5
7
4
7a
Summenformel: C21H21NO3
3a
1
N
3
2
CH 3
3''
1'
6'
CH 3
1 V
1''
CO 2CH 3
2''
2'
5'
3'
1'''
4'
1 IV
OCH 3