Table 1.
J7,8 Values, specific optical rotations and ECD data of 8,4′-oxyneolignians.
| No. | C-7 & C-8 Configurations |
J7,8 Values | Specific Optical Rotations | ECD Data | ||||
|---|---|---|---|---|---|---|---|---|
| J7,8 (Hz) | Solvent | [α]D | Solvent | T (°C) | Δε | λ (nm) | ||
| 1a | (7R,8S)-erythro | 3.5 | CD3OD | +3.3 | MeOH | 25 | +2.25 | 239 |
| 1b | (7S,8R)-erythro | 3.5 | CD3OD | −4.7 | MeOH | 25 | −2.75 | 239 |
| 2a | (7R,8R)-threo | 6.8 | CD3OD | −21.7 | MeOH | 25 | −3.45 | 231 |
| 2b | (7S,8S)-threo | 6.8 | CD3OD | +16.0 | MeOH | 25 | +2.83 | 232 |
| 3a | (7S,8S)-threo | 8.8 | CDCl3 | +18.0 | MeOH | 20 | −1.12 | 239 |
| 3b | (7R,8R)-threo | 8.8 | CDCl3 | −20.0 | MeOH | 20 | +1.40 | 237 |
| 4a | (7R,8S)-erythro | 2.6 | CDCl3 | +20.5 | MeOH | 20 | +2.38 | 245 |
| 4b | (7S,8R)-erythro | 2.6 | CDCl3 | −22.0 | MeOH | 20 | −1.89 | 243 |
| 5a | (7R,8S)-erythro | 3.3 | CDCl3 | +32.0 | MeOH | 20 | +0.25 | 238 |
| 5b | (7S,8R)-erythro | 3.3 | CDCl3 | −28.2 | MeOH | 20 | −0.01 | 238 |
| 6a | (7S,8S)-threo | 6.9 | CDCl3 | +36.7 | MeOH | 20 | +8.92 | 239 |
| 6b | (7R,8R)-threo | 6.9 | CDCl3 | −33.5 | MeOH | 20 | −6.50 | 240 |
| 7a | (7R,8R)-threo | 8.0 | CDCl3 | −28.5 | MeOH | 20 | +9.64 | 230 |
| 7b | (7S,8S)-threo | 8.0 | CDCl3 | +26.9 | MeOH | 20 | −8.74 | 230 |
| 8a | (7R,8S)-erythro | 7.2 | CDCl3 | −31.0 | MeOH | 20 | −3.55 | 240 |
| 8b | (7S,8R)-erythro | 7.2 | CDCl3 | +29.0 | MeOH | 20 | +2.80 | 240 |
| 9a | (7S,8S)-threo | 7.4 | CDCl3 | +34.0 | MeOH | 20 | +3.70 | 244 |
| 9b | (7R,8R)-threo | 7.4 | CDCl3 | −34.0 | MeOH | 20 | −2.81 | 243 |
| 10a | (7R,8R)-threo | 6.5 | CDCl3 | −28.0 | MeOH | 20 | +16.90 | 240 |
| 10b | (7S,8S)-threo | 6.5 | CDCl3 | +32.0 | MeOH | 20 | −17.65 | 238 |
| 11a | (7R,8R)-threo | 7.6 | CDCl3 | −20.0 | MeOH | 20 | −6.57 | 238 |
| 11b | (7S,8S)-threo | 7.6 | CDCl3 | +21.0 | MeOH | 20 | +8.87 | 242 |
| 12a | (7R,8S)-erythro | 4.7 | CDCl3 | −31.0 | MeOH | 20 | −3.55 | 240 |
| 12b | (7S,8R)-erythro | 4.7 | CDCl3 | +29.0 | MeOH | 20 | +2.80 | 240 |
| 13a | (7S,8R)-erythro | 3.0 | CDCl3 | +17.1 | CHCl3 | 20 | −1.03 | 232 |
| 13b | (7R,8S)-erythro | 3.0 | CDCl3 | −16.2 | CHCl3 | 20 | +1.03 | 232 |
| 14a | (7S,8S)-threo | 6.3 | CDCl3 | −35.1 | CHCl3 | 20 | −1.14 | 240 |
| 14b | (7R,8R)-threo | 6.3 | CDCl3 | +32.6 | CHCl3 | 20 | +1.17 | 240 |
| 15a | (7R,8R)-threo | 8.1 | CDCl3 | +30.4 | CHCl3 | 20 | +1.58 | 240 |
| 15b | (7S,8S)-threo | 8.1 | CDCl3 | −29.8 | CHCl3 | 20 | −1.54 | 240 |
| 16a | (7S,8R)-erythro | 3.3 | CDCl3 | +16.6 | CHCl3 | 20 | +3.18 | 234 |
| 16b | (7R,8S)-erythro | 3.3 | CDCl3 | −16.4 | CHCl3 | 20 | −3.20 | 234 |
| 17a | (7R,8R)-threo | 8.0 | CDCl3 | +7.0 | MeOH | 20 | - | - |
| 17b | (7S,8S)-threo | 8.0 | CDCl3 | −7.0 | MeOH | 20 | - | - |
| 18a | (7S,8R)-erythro | 4.7 | CDCl3 | +20.0 | MeOH | 20 | +11.17 | 230 |
| 18b | (7R,8S)-erythro | 4.7 | CDCl3 | −18.0 | MeOH | 20 | −4.00 | 235 |
| 19a | (7S,8S)-threo | 6.1 | CD3OD | +18.0 | MeOH | 20 | +1.70 | 230 |
| 19b | (7R,8R)-threo | 6.1 | CD3OD | −18.0 | MeOH | 20 | −1.20 | 230 |
| 20a | (7R,8S)-erythro | 4.8 | CD3OD | −10.0 | MeOH | 20 | +2.70 | 232 |
| 20b | (7S,8R)-erythro | 4.8 | CD3OD | +8.0 | MeOH | 20 | −2.82 | 233 |
| 21a | (7S,8R)-erythro | 5.4 | CD3OD | +15.0 | MeOH | 20 | +3.15 | 228 |
| 21b | (7R,8S)-erythro | 5.4 | CD3OD | −15.0 | MeOH | 20 | −2.65 | 228 |
| 22a | (7S,8S)-threo | 7.7 | CDCl3 | +17.2 | MeOH | 20 | −0.59 | 233 |
| 22b | (7R,8R)-threo | 7.7 | CDCl3 | −19.0 | MeOH | 20 | +0.51 | 232 |
| 23a | (7R,8R)-threo | 7.6 | CDCl3 | −24.5 | MeOH | 20 | - | - |
| 23b | (7S,8S)-threo | 7.6 | CDCl3 | +26.0 | MeOH | 20 | - | - |
| 24a | (7R,8S)-erythro | 4.6 | CDCl3 | −18.0 | MeOH | 20 | +12.20 | 241 |
| 24b | (7S,8R)-erythro | 4.6 | CDCl3 | +22.0 | MeOH | 20 | −10.81 | 241 |
| 25a | (7S,8S)-threo | 6.8 | CDCl3 | +23.0 | MeOH | 20 | +0.57 | 240 |
| 25b | (7R,8R)-threo | 6.8 | CDCl3 | −25.0 | MeOH | 20 | −1.05 | 237 |