Arbeit komplett 12.07.2003 komplett Annahmeste - ArchiMeD

10 Experimenteller, chemisch-präparativer Teil 224
1 H-NMR δ [ppm]:
(300 MHz) Aceton-d6
13 C-NMR δ [ppm]:
(75 MHz) Aceton-d6
3.67-3.68 (s, s, 6H, 2xCH3, 1'''-H und N-CH3); 6.42 (d,
3 J=15.97, 1H, CH, 2''-H ((E)-Isomer)); 7.28-7.37 (m, 2H,
2xCH, 5-H, 6-H); 7.43 (dd, 3 J=8.82, 3 J(H, F)=8.82, 2H,
2xCH, 3'-H, 5'-H); 7.55-7.61 (m, 3H, 3xCH, 2'-H, 6'-H, 7-H);
7.63, d, 3 J=15.97, 1H, CH, 3''-H ((E)-Isomer)); 8.00 (dd,
3 J=6.91, 4 J=1.19, 1H, CH, 4-H)
32.4 (CH3, N-CH3); 52.2 (CH3, C-1'''); 111.8 (Cq, C-3);
112.4 (CH, C-7); 113.9 (CH, C-2''); 117.6 (2xCH, 2 J(C,
F)=21.48, C-3' und C-5'); 122.1 (CH, C-4); 123.5 (CH, C-5);
124.9 (CH, C-6); 127.2 (Cq, C-3a); 128.3 (Cq, 4 J(C,
F)=3.39, C-1'); 135.0 (2xCH, 3 J(C, F)=7.91, C-2' und C-6');
140.0 (Cq, C-7a); 140.0 (CH, C-3''); 146.2 (Cq, C-2); 164.2
(Cq, 1 J(C, F)=247.53, C-4'); 169.5 (Cq, C-1'')
EI-MS (70 eV); m/z (%) 309.3 (100.00), 278.3 (45.73), 249.0 (94.62), 235.2 (72.18),
149.3 (37.74), 106.3 (99.65), 77.3 (38.39), 56.5 (30.52),
43.9 (65.04)
Elementaranalyse (%): Ber.: C: 74.29 H: 5.61 N: 4.33
Gef.: C: 74.11 H: 5.60 N: 4.24
UV/VIS [nm]: lgε
CH2Cl2
λmax: 235.0 (5.33); λ1: 342.6 (5.30); λ2: 283.6 (5.25)
IR (KBr); ö [cm -1 ] 3070 (w) 3023 (w) 2949 (w) 2898 (w) 1700 (s)
1621 (s) 1606 (s) 1574 (m) 1537 (m) 1494 (s)
1470 (s) 1436 (s) 1417 (s) 1370 (m) 1358 (m)
1343 (m) 1304 (s) 1293 (s) 1267 (s) 1262 (s)
1233 (s) 1213 (s) 1175 (s) 1135 (s) 1103 (w)
1073 (m) 1041 (m) 989 (w) 976 (m) 931 (w)
865 (m) 859 (m) 844 (m) 816 (w) 801 (m)
766 (w) 755 (m) 740 (m) 731 (m) 671 (w)
10.3.2.17 (E)-3-[2-(4-Fluorophenyl)-1H-indol-3-yl]-acrylsäureethylester (78)
Summenformel: C19H16FNO2
6
5
7
4
7a
3a
1
N
H
3
3''
2
1'
6'
1''
2''
2'
CO2C2H5
5'
3'
4'
1''', 2'''
F