Spectral data for metabolites derived from compound I
| Compound | IR (neat) γmax | 1H NMR (δ) CDCl3 | MS (LRMS and HRMS) |
|---|---|---|---|
| Ia | 3400 cm−1(—OH), 1703 and 1627 cm−1 (conjugated carbonyl) | 4.2 (s, 2H, H—9), 2.8 (d, 2H, J = 10.8 Hz, H—3), 2.5 (2d, 2H, J = 7.5 Hz, H—5), 2.27 (s, 4H, H—8 and H—4), 1.1 (d, 3H, J = 7.5 Hz, H—6) | m/z: 154 (M+, bp), 139 (M+—CH3), 136 (M+—H2O), 125 (M+—C2H5), 121 (M+—CH3—H2O), 111 (M+—CO—H2O) HRMS: C9H14O2 requires 154.0994, found 154.0997 |
| Ib | 3400 cm−1 (—OH), 1680 and 1610 cm−1 (conjugated carbonyl) | 4.3 (s, 2H, H—8), 2.2–2.6 (m, 5H, ring protons), 1.9 (s, 3H, H—9), 1.05 (d, 3H, J = 6.0 Hz, H—6) | m/z: 154 (M+), 139 (M+—CH3), 136 (M+—H2O), 121 (M+—CH3—H2O) HRMS: C9H14O2 requires 154.0994, found 154.0996 |
| Ic | 3440 cm−1 (—OH), 1690 and 1629 cm−1 (conjugated carbonyl) | 2.6 (bs, 2H, H—3), 2.4 (s, 2H, H—5), 2.1 (s, 3H, H—8), 1.77 (s, 3H, H—9) 1.38 (s, 3H, H—6) | m/z: 154 (M+), 139 (M+—CH3), 136 (M+—H2O), 121 (M+—CH3—H2O), 111 (M+—CO—CH3), 96 (M+—C3H6O) HRMS: C9H14O2 requires 154.0994, found 154.1001 |
| Id | 3100 cm−1 (carboxyl), 1706 and 1690 cm−1 (carbonyl groups) | 2.35 (s, 3H, H—8), 2.06–2.6 (m, 5H, ring protons), 1.11 (d, 3H, J = 6.44 Hz, H—6) | m/z: 168 (M+), 150 (M+—H2O), 140 (M+—CO), 122 (M+—CO—H2O) |
| Ie | 1695 and 1620 cm−1 (conjugated carbonyl) | 6.05 (s, 1H, H—2), 3.1 (s, 2H, H—4), 2.3 (s, 3H, H—8), 2.1 (s, 3H, H—6), 1.86 (s, 3H, H—9) | m/z: 136 (M+, bp), 121 (M+—CH3), 93 (M+—CO—CH3) HRMS: C9H12O requires 136.0888, found 136.0886 |
| If | 3390 cm−1(—OH), 1690 and 1620 cm−1 (conjugated carbonyl) | 4.6 (s, 1H, H—3), 2.7 (2d, 2H, J = 8.1 Hz, H—5), 2.3 (bs, 4H, H—8, and H—4), 2.04 (s, 3H, H—9), 1.0 (d, 3H, J = 6.9 Hz, H—6) | m/z: 154 (M+), 139 (M+—CH3), 136 (M+—H2O), 121 (M+—CH3—H2O), 111 (M+—CO—CH3), 83 (M+—C4H7O, bp) HRMS: C9H14O2 requires 154.0994, found 154.0993 |