Table 1.
1H- and 13C-NMR spectroscopic data of compounds 1, 2 and 5 (400 MHz for 1H-NMR and 100 MHz for 13C-NMR, in DMSO-d6, δ in ppm, J in Hz).
| Position | 1 | 2 | 5 | |||
|---|---|---|---|---|---|---|
| δH | δC | δH | δC | δH | δC | |
| 1 | - | 135.0 | - | 137.1 | - | 131.8 |
| 2 | 6.58 (1H, s) | 114.5 | 6.54 (1H, d, J = 1.6 Hz) | 114.3 | 6.82 (1H, d, J = 2 Hz) | 129.2 |
| 3 | - | 149.7 | - | 149.7 | - | 127.1 |
| 4 | - | 143.7 | - | 143.6 | - | 152.9 |
| 5 | - | 134.3 | - | 134.3 | 6.67 (1H, d, J = 8.8 Hz) | 114.7 |
| 6 | 6.43 (1H, d, J = 1.6 Hz) | 119.8 | 6.40 (1H, d, J = 1.6 Hz) | 119.6 | 6.80 (1H, dd, J = 8.8, 2 Hz) | 126.2 |
| 7 | 2.73 (2H, m) | 35.7 | 2.57 (2H, m) | 36.5 | 2.62 (2H, m) | 36.4 |
| 8 | 2.93 (2H, m) | 34.6 | 2.57 (2H, m) | 37.1 | 2.54 (2H, m) | 37.6 |
| 9 | -- | 136.9 | - | 139.6 | - | 139.7 |
| 10 | - | 118.6 | 6.13 (1H, s) | 106.2 | 6.12 (1H, s) | 106.3 |
| 11 | - | 155.4 | - | 155.7 | - | 155.7 |
| 12 | 6.75 (1H, d, J = 0.8 Hz) | 95.4 | - | 111.7 | - | 111.7 |
| 13 | - | 155.4 | - | 155.7 | - | 155.7 |
| 14 | 6.58 (1H, s) | 111.7 | 6.13 (1H, s) | 106.2 | 6.12 (1H, s) | 106.3 |
| 1′ | 3.18 (2H, d, J = 7.2 Hz) | 28.3 | 3.19 (2H, d, J = 7.2 Hz) | 28.3 | 3.16 (2H, d, J = 7.2 Hz) | 28.2 |
| 2′ | 5.16 (1H, t, J = 7.2 Hz) | 123.5 | 5.17 (1H, m) | 123.5 | 5.24 (1H, t, J = 7.2Hz) | 123.1 |
| 3′ | - | 130.9 | - | 131.0 | - | 130.9 |
| 4′ | 1.66 (3H, s) | 17.7 | 1.67 (3H, s) | 17.7 | 1.65 (3H, s) | 17.7 |
| 5′ | 1.66 (3H, s) | 25.5 | 1.67 (3H, s) | 25.5 | 1.67 (3H, s) | 25.5 |
| 1′′ | 6.83 (1H, d, J = 2.0 Hz) | 105.1 | 3.12 (2H, d, J = 6.8 Hz) | 21.9 | 3.12 (2H, d, J = 6.8 Hz) | 21.9 |
| 2′′ | 7.71 (1H, d, J = 2.0 Hz) | 143.4 | 5.17 (1H, m) | 123.9 | 5.15 (1H, t, J = 6.8 Hz) | 123.9 |
| 3′′ | - | - | - | 129.0 | - | 129.0 |
| 4′′ | - | - | 1.59 (3H, s) | 17.7 | 1.59 (3H, s) | 17.7 |
| 5′′ | - | - | 1.68 (3H, s) | 25.5 | 1.68 (3H, s) | 25.5 |
| 4-OCH3 | 3.64 (3H, s) | 59.6 | 3.64 (3H, s) | 59.6 | ||