Table 1.
1H and 13C NMR Data of compounds 1 – 4.
| 1b | 2b | 3b | 4b | |||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| position | δ Cc | multi | δH | multi (J in Hz)e | δ Cc | multi | δH | multi (J in Hz)e | δCc | multi | δH | multi (J in Hz)e | δCc | multi | δH | multi (J in Hz)e |
| 2 | 160.5 | C | - | - | 159.1 | C | - | - | 161.1 | C | - | - | 158.9 | C | - | - |
| 3 | 115.5 | CH | 6.405 | s | 121.8 | C | - | - | 115.1 | CH | 6.382 | s | 119.2 | C | - | - |
| 4 | 155.1 | C | - | - | 153.7 | C | - | - | 156.3 | C | - | - | 155.1 | C | - | - |
| 4a | 120.2 | C | - | - | 123.5 | C | - | - | 118.4 | C | - | - | 122.3 | C | - | - |
| 5 | 125.9 | CH | 7.433 | dd (2.50, 0.41) | 128.4 | CH | 7.176 | dd (2.50, 0.44) | 125.3 | CH | 7.494 | dd (8.58, 0.76) | 126.5 | CH | 7.250 | dd (8.61, 0.22) |
| 6 | 129.4 | C | - | - | 131.4 | C | - | - | 128.8 | CH | 7.322 | dd (8.58, 1.98) | 131.0 | CH | 7.326 | dd (8.61, 2.05) |
| 7 | 131.8 | CH | 7.632 | dd (8.84, 2.50) | 134.3 | C | 7.677 | dd (8.87, 2.50) | 135.5 | C | - | - | 134.0 | CH | - | - |
| 8 | 118.6 | CH | 7.455 | dd (8.84, 0.41) | 120.1 | CH | 7.495 | dd (8.87, 0.44) | 117.7 | CH | 7.504 | dd (1.98, 0.76) | 118.3 | CH | 7.548 | dd (2.05, 0.22) |
| 8a | 152.6 | C | - | - | 153.5 | C | - | - | 155.1 | C | - | - | 154.2 | C | - | - |
| 9 | 134.6 | C | - | - | 133.8 | C | - | - | 138.3 | C | - | - | 140.0 | C | - | - |
| 10 | 128.2 | CH | 7.527 | dddd (2.04, 7.66, 1.25, 0.64) | 130.0 | CH | 7.422 | dddd (1.92, 7.67, 1.25, 0.62) | 128.9 | CH | 7.512 | dddd (2.24, 7.67, 0.33, 1.30) | 129.5 | CH | 7.395 | dddd (1.63, 7.68, 0.63, 1.06) |
| 11 | 128.8 | CH | 7.599 | dddd (7.66, 0.64, 1.25, 7.55) | 130.2 | CH | 7.591 | dddd (1.25, 7.57, 0.72, 7.67) | 129.4 | CH | 7.570 | dddd (7.76, 0.33, 1.33, 7.54) | 130.0 | CH | 7.559 | dddd (7.68, 0.63, 1.28, 7.49) |
| 12 | 129.8 | CH | 7.592 | dd (1.25, 7.55) | 131.2 | CH | 7.588 | dd (7.57, 1.25) | 130.4 | CH | 7.566 | dd (1.30, 7.54) | 130.5 | CH | 7.565 | dd (7.49, 1.06) |
| 13 | 128.8 | CH | 7.599 | dddd (7.66, 0.64, 1.25, 7.55) | 130.2 | CH | 7.591 | dddd (1.25, 7.57, 0.72, 7.67) | 129.4 | CH | 7.570 | dddd (7.76, 0.33, 1.33, 7.54) | 130.0 | CH | 7.559 | dddd (7.68, 0.63, 1.28, 7.49) |
| 14 | 128.2 | CH | 7.527 | dddd (2.04, 7.66, 1.25, 0.64) | 130.0 | CH | 7.422 | dddd (1.92, 7.67, 1.25, 0.62) | 128.9 | CH | 7.512 | dddd (2.24, 7.67, 0.33, 1.30) | 129.5 | CH | 7.395 | dddd (1.63, 7.68, 0.63, 1.06) |
| 15 | - | - | - | - | 165.3 | C | - | - | - | - | - | - | 165.3 | C | - | - |
| 16 | - | - | - | - | 61.5 | CH2 | 4.052 | q (7.01) | - | - | - | - | 62.9 | CH2 | 4.040 | q (7.12) |
| 17 | - | - | - | - | 12.6 | CH3 | 0.966 | t (7.01) | - | - | - | - | 14.0 | CH3 | 0.957 | t (7.12) |
b
1H NMR data were obtained for the synthetic compounds.
c
13C NMR chemical shifts were obtained from DEPTQ.
e
The J-coupling values resolved from iterative full 1H spin analysis using PERCH, given with 10 mHz precision.