Table 1. 1H NMR (500 MHz) and 13C NMR (125 MHz) Data of Compounds 1–4 in CD3ODa.
1 |
2 |
3 |
4 |
|||||
---|---|---|---|---|---|---|---|---|
no. | δC | δH mult. (J in Hz) | δC | δH mult. (J in Hz) | δC | δH mult. (J in Hz) | δC | δH mult. (J in Hz) |
1 | 131.9 | 131.8 | 132.4 | 131.6 | ||||
2 | 112.5 | 6.91 d (2.0) | 112.3 | 6.97 d (1.9) | 112.3 | 6.90 d (1.8) | 112.2 | 6.89 d (1.8) |
3 | 148.9 | 149.1 | 148.9 | 148.9 | ||||
4 | 147.4 | 147.5 | 115.7 | 6.76 d (1.8) | 115.7 | 6.76 d (1.8) | ||
5 | 119.5 | 6.70 d (8.2) | 119.4 | 6.92 d (8.0) | 147.2 | 147.2 | ||
6 | 121.8 | 6.61 dd (8.2, 2.0) | 121.5 | 6.82 dd (8.0, 1.9) | 121.7 | 6.76 d (1.8) | 121.8 | 6.76 d (1.8) |
7 | 81.9 | 4.46 d (6.4) | 82.6 | 4.53 d (5.9) | 82.0 | 4.60 d (5.9) | 83.9 | 4.49 d (5.8) |
8 | 85.9 | 4.27 m | 86.5 | 4.26 td (5.9, 5.9, 4.0) | 86.8 | 4.15 m | 86.8 | 4.15 m |
9 | 62.3 | 3.82 m | 62.4 | 3.63 dd (11.7, 4.0) | 62.2 | 3.90 dd (12.1, 4.7) | 62.2 | 3.88 m |
3.84 m | 3.42 m | 3.65 m | 3.63 m | |||||
1’ | 137.9 | 137.8 | 139.7 | 139.8 | ||||
2’ | 114.2 | 6.75 d (2.0) | 114.2 | 6.83 d (2.0) | 107.1 | 6.50 brs | 107.0 | 6.50 brs |
3’ | 151.8 | 151.8 | 154.3 | 154.3 | ||||
4’ | 147.3 | 148.2 | 135.0 | 135.1 | ||||
5’ | 115.7 | 6.73 d (8.0) | 116.0 | 6.77 d (8.1) | 154.3 | 154.3 | ||
6’ | 122.1 | 6.79 dd (8.0, 2.0) | 121.9 | 6.69 dd (8.1, 2.0) | 107.1 | 6.50 brs | 107.0 | 6.50 brs |
7’ | 32.6 | 2.58 m | 32.7 | 2.62 m | 33.4 | 2.62 m | 33.4 | 2.62 m |
8’ | 35.5 | 1.78 m | 35.5 | 1.81 m | 35.4 | 1.82 m | 35.4 | 1.82 m |
9’ | 62.2 | 3.53 t (6.5) | 62.3 | 3.56 t (6.5) | 61.4 | 3.56 t (6.5) | 61.3 | 3.56 t (6.5) |
1” | 65.4 | 3.41 m | 65.7 | 3.42 m | 65.6 | 3.43 m | ||
2” | 15.6 | 1.16 t (7.0) | 15.6 | 1.13 t (7.0) | 15.6 | 1.18 t (7.0) | ||
3-OCH3 | 56.4 | 3.78 s | 56.5 | 3.82 s | 56.5 | 3.83 s | 56.4 | 3.83 s |
7-OCH3 | 57.3 | 3.26 s | ||||||
3’-OCH3 | 56.5 | 3.75 s | 56.6 | 3.83, s | 56.6 | 3.75 s | 56.6 | 3.76 s |
5’-OCH3 | 56.6 | 3.75 s | 56.6 | 3.76 s |
Assignments aided by HSQC, 1H-1H COSY, and HMBC experiments.