Substitution von molekularen Klammern an den Naphthalin ...

Substitution von molekularen Klammern an den Naphthalin ... Substitution von molekularen Klammern an den Naphthalin ...

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08.12.2012 Aufrufe

Experimenteller Teil 8.2 8.80 8.1 8.64 8.60 8.25 24 H2N 8.0 7.70 O 7.9 23 2 3 7.76 7.15 1 7.72 6.60 18 7.68 7.64 6.05 17 7.60 5.50 21 OH 7.56 4.95 7.32 7.26 7.20 4.58 4.56 4.54 4.40 3.85 4 5 6 7 OH 22 8 9 10 16 19 20 15 14 13 3.30 25 12 11 O 2.75 NH2 26 meso-63d: 1 H-NMR (500 MHz, DMSO-d6): δ [ppm] =2.26 (d, 2H, 2 J(19i-H, 19a-H)= 7.9 Hz, 19i-H, 20i-H), 2.36 (d, 2H, 19a-H, 20a-H), 4.56/4.57 (s, 4H, 6-H, 8-H, 15-H, 17-H), 7.27 (s, 2H, NH), 7.59, 7.60 (s, 4H, 5-H, 9-H, 14-H, 18-H), 7.64 (d, 2H, 3 J(4- H, 3-H)= 8.6 Hz, 4-H, 13-H), 7.72 (dd, 2H, 3-H, 12-H), 7.90 (s, 2H, NH), 8.17 (s, 2 H, 1-H, 10-H), 8.60, 8.61 (s, 2H, OH). 13 C-NMR (126 MHz, DMSO-d6): δ [ppm] = 46.26, 46.38 (d, C-6, C-8, C-15, C-17), 63.86 (t, C-19, C-20), 118.84 (d, C-5, C-9), 119.80 (d, C-14, C-18), 123.55 (d, C-3, C-11), 127.43 (d, C-4, C-10), 127.43 (d, C-1, C-13), 130.60, 130.64 (s, C-4a, C-9a, C-13a, C-18a), 132.95 (s, C-2, C-12), 133.75, 133.90 (s, C-6a, C-7a, C-15a, C- 16a), 139.12, 139.16 (s, C-7, C-16), 148.35 (s, C-5a, C-8a), 149.56 (s, C-13a, C- 17a), 168.03 (s, C-23, C-25). 2.20 232

Experimenteller Teil IR (KBr): ν ~ (cm -1 ) = 3462-3212 (NH), 2993-2862 (CH), 1655 (C=O), 1640 (C=O), 1616 (C=C), 1284 (C-O). MS (70 eV), m/z (%): 524 (15) [M + ], 488 (100) [M + - 2 NH2]. MS-ESI (485 eV) m/z Molmasse: 524.174 ber. C34H24N2O4 547.152 gef. C34H24NaN2O4 233

Experimenteller Teil<br />

8.2<br />

8.80<br />

8.1<br />

8.64 8.60<br />

8.25<br />

24<br />

H2N 8.0<br />

7.70<br />

O<br />

7.9<br />

23<br />

2<br />

3<br />

7.76<br />

7.15<br />

1<br />

7.72<br />

6.60<br />

18<br />

7.68<br />

7.64<br />

6.05<br />

17<br />

7.60<br />

5.50<br />

21<br />

OH<br />

7.56<br />

4.95<br />

7.32 7.26 7.20<br />

4.58 4.56 4.54<br />

4.40<br />

3.85<br />

4 5 6 7<br />

OH<br />

22<br />

8 9 10<br />

16<br />

19 20<br />

15<br />

14<br />

13<br />

3.30<br />

25<br />

12<br />

11<br />

O<br />

2.75<br />

NH2 26<br />

meso-63d: 1 H-NMR (500 MHz, DMSO-d6): δ [ppm] =2.26 (d, 2H, 2 J(19i-H, 19a-H)=<br />

7.9 Hz, 19i-H, 20i-H), 2.36 (d, 2H, 19a-H, 20a-H), 4.56/4.57 (s, 4H, 6-H, 8-H, 15-H,<br />

17-H), 7.27 (s, 2H, NH), 7.59, 7.60 (s, 4H, 5-H, 9-H, 14-H, 18-H), 7.64 (d, 2H, 3 J(4-<br />

H, 3-H)= 8.6 Hz, 4-H, 13-H), 7.72 (dd, 2H, 3-H, 12-H), 7.90 (s, 2H, NH), 8.17 (s, 2<br />

H, 1-H, 10-H), 8.60, 8.61 (s, 2H, OH).<br />

13 C-NMR (126 MHz, DMSO-d6): δ [ppm] = 46.26, 46.38 (d, C-6, C-8, C-15, C-17),<br />

63.86 (t, C-19, C-20), 118.84 (d, C-5, C-9), 119.80 (d, C-14, C-18), 123.55 (d, C-3,<br />

C-11), 127.43 (d, C-4, C-10), 127.43 (d, C-1, C-13), 130.60, 130.64 (s, C-4a, C-9a,<br />

C-13a, C-18a), 132.95 (s, C-2, C-12), 133.75, 133.90 (s, C-6a, C-7a, C-15a, C-<br />

16a), 139.12, 139.16 (s, C-7, C-16), 148.35 (s, C-5a, C-8a), 149.56 (s, C-13a, C-<br />

17a), 168.03 (s, C-23, C-25).<br />

2.20<br />

232

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