1H (600 MHz) and 13C NMR (150 MHz) NMR data for compounds 1–3.
Position | 1a | 2b | 3b | |||
---|---|---|---|---|---|---|
δ H (J in Hz) | δ C | δ H (J in Hz) | δ C | δ H (J in Hz) | δ C | |
1 | 132.3 | |||||
2 | 8.09, s | 156.0 | 8.19, s | 157.2 | 6.98, br s | 112.2 |
3 | 122.9 | 122.0 | 145.6 | |||
4 | 182.5 | 182.8 | 149.4 | |||
4a | 104.8 | 106.0 | ||||
5 | 157.2 | 158.1 | 130.4 | |||
6 | 106.5 | 107.0 | 6.98, br s | 116.6 | ||
7 | 159.7 | 160.1 | 5.59, d (16.2) | 134.3 | ||
8 | 103.2 | 103.8 | 6.19, m | 124.3 | ||
8a | 153.3 | 154.7 | ||||
9 | 2.74, dd (17.4, 10.2) | 21.8 | 2.73, dd (16.8, 10.8) | 22.6 | 4.08, dd (6.0, 1.2) | 74.3 |
2.98, dd (17.4, 5.4) | 2.99, dd (16.8, 4.8) | |||||
8-CH3 | 2.22, s | 7.7 | 2.23, s | 7.6 | ||
3-OCH3 | 3.90, s | 56.8 | ||||
9-OCH3 | 3.39, s | 58.0 | ||||
1′ | 120.4 | 119.8 | 134.3 | |||
2′ | 156.2 | 156.8 | 6.96, d (1.8) | 110.6 | ||
3′ | 7.10, dd (7.8, 1.2) | 119.8 | 6.94, dd (7.8, 1.2) | 117.2 | 149.1 | |
4′ | 7.36, ddd (7.8, 7.8, 1.8) | 130.8 | 7.29, ddd (7.8, 7.8, 1.8) | 132.7 | 147.7 | |
5′ | 7.00, ddd (7.8, 7.8, 1.2) | 121.3 | 6.92, ddd (7.8, 7.8, 1.2) | 120.7 | 6.79, d (7.8) | 116.2 |
6′ | 7.19, dd (7.8, 1.8) | 129.9 | 7.26, dd (7.8, 1.8) | 130.9 | 6.84, dd (7.8, 1.8) | 119.9 |
7′ | 5.50, d (6.6) | 89.7 | ||||
8′ | 3.63, m | 52.7 | ||||
9′ | 3.65, m | 75.7 | ||||
3.72, m | ||||||
3′-OCH3 | 3.84, s | 56.4 | ||||
9′-OCH3 | 3.41, s | 59.3 | ||||
1′′ | 131.1 | 131.4 | ||||
2′′ | 6.92, d (1.8) | 109.1 | 6.73, s | 105.3 | ||
3′′ | 147.0 | 149.4 | ||||
4′′ | 146.1 | 136.7 | ||||
5′′ | 6.95, d (7.8) | 114.6 | 149.4 | |||
6′′ | 6.91, dd (7.8, 1.8) | 120.0 | 6.73, s | 105.3 | ||
7′′ | 5.02, d (9.0) | 81.0 | 5.02, d (8.4) | 82.0 | ||
8′′ | 2.25, m | 39.7 | 2.26, m | 40.8 | ||
9′′ | 3.55, dd (10.8, 4.8) | 63.4 | 3.43, dd (10.8, 4.8) | 63.4 | ||
3.65, dd (10.8, 4.8) | 3.55, dd (10.8, 4.8) | |||||
3′′-OCH3 | 3.92, s | 56.2 | 3.87, s | 56.8 | ||
5′′-OCH3 | 3.87, s | 56.8 | ||||
5-OH | 12.54, s |
Recorded in CDCl3.
Recorded in methanol-d4.