Substitution von molekularen Klammern an den Naphthalin ...

Experimenteller Teil
O
24
H3CO 23
2
3
1
18
17
21
OH
16
19 20
4 5 6 7
OH
22
8 9 10
1 H-NMR (500 MHz, CD3OD): δ [ppm] = 2.34, 2.36 (dt, 2H, 2 J(19i-H, 19a-H)= 8.2
Hz, 3 J (19i-H, 6-H)= 1.6 Hz, 19i-H, 20i-H), 2.47, 2.48 (dt, 2H, 19a-H, 20a-H), 3.80
(s, 3H, 26-H), 4.52 (t, 2H, 8-H, 15-H), 4.55 (m, 2H, 6-H, 17-H), 6.97 (m, 2H, 11-H,
12-H), 7.05 (d, 1H, 3 J (4-H, 3-H) = 8.5 Hz, 4-H), 7.11 (s, 1H, 5-H), 7.25 (s, 1H, 18-
H), 7.27 (m, 2H, 10-H, 13-H), 7.38 (s, 2H, 9-H, 14-H), 7.48 (dd, 1H, 3 J (4-H, 3-H) =
8.5 Hz, 4 J (3-H, 1-H) = 1.7, 3-H), 8.32, 8.33 (s, 1H, 1-H).
13 C-NMR (126 MHz, CD3OD): δ [ppm] = 48.14 (d, C-6), 48.28 (d, C-8, C-15), 48.38
(d, C-17), 52.00 (q, C-24), 64.96, 64.02 (t, C-19, C-20), 120.26 (d, C-5), 120.39,
120.40 (d, C-9, C-14), 121.37 (d, C-18), 125.04 (d, C-11, C-12), 125.79 (d, C-3),
127.09 (s, C-2), 128.39 (d, C-10, C-13), 128.67 (d, C-1), 131.25 (d, C-4), 132.31 (s,
C-4a), 133.47/ 133.48 (s, C-9a, C-13a), 135.82 (s, C-18a), 135.92 (s, C-5a),
136.07 (s, C-6a, C-7a, C-15a, C-16a), 136.49/ 136.56 (s, C-7, C-16), 140.82 (s, C-
17a), 148.67/ 148.68 (s, C-8a, C-14a), 149.60 (s, C-18), 151.60 (C-17a), 169.2 (s,
C=O).
Die Klammer 71d bildet in CD3OD Dimere. Die im 1 H-NMR-Spektrum
beobachteten δ-werte sind Konzentrationsabhängig und können in einem anderen
Konzentrationsbereich andere Werte aufweisen.
IR (KBr): ν ~ (cm -1 ): 3181 (C-OH), 2978 (C-H), 1689 (C=O), 1610 (C=C), 1275 (C-
O), 1176 (C-O).
MS-ESI (376 eV): Molmasse: 496.167 ber. C34H24O4
-MS: 495.158 gef. C33H23O4
15
14
13
12
11
280