Spektraris NMR
20-O-cinnamoyl-5-epi-canadensene
Common Name: 20-O-cinnamoyl-5-epi-canadensene
Synonyms: (3E,8E)-2α,7β,9,10β,13α-Pentaacetoxy-5α-hydroxy-20- cinnamoyloxy-3,8-secotaxa-3,8,11-triene
CAS Registry Number:
InChI: InChI=1S/C31H44O11/c1-11-22-12-27(40-19(6)34)23-13-25(38-17(4)32)15(2)28(31(23,9)10)30(42-21(8)36)29(41-20(7)35)16(3)26(14-24(22)37)39-18(5)33/h12,23-27,30,37H,11,13-14H2,1-10H3/b22-12+,29-16-/t23-,24-,25?,26?,27?,30?/m0/s1
InChIKey: LZCRCYVERQXDKA-JXQSXQNZSA-N
Formula: C39H48O13
Molecular Weight: 724.1749
Exact Mass: 724.1751
NMR Solvent: CDCl3
MHz: 500 (1H); 125 (13C)
Calibration:
NMR references: Shi, Q. W.
Nikolakakis, A.
Sauriol, F.
Mamer, O.
Zamir, L. O. Canadensenes: Natural and Semi-Synthetic Analogues. Can. J. Chem. 2003, 81, 406.
Species: Taxus canadensis needles in September 1997 at Taxus canadensis needles in September 1997 at St-Jean-sur-Richelieu, Quebec, Canada.
Notes: calibration unknown. Cinnamoyloxyl not shown in InChI on carbon 20.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 1 | 1.82 | dd | 6.5, 4.5 |
| 2 | 5.84 | dd | 11.8, 4.7 |
| 3 | 6.5 | d | 11.7 |
| 5 | 4.55 | o.m | |
| 6a | 2.63 | ddd | 16.2, 7.8, 2.7 |
| 6b | 2.03 | o.m | |
| 7 | 5.08 | d | 7.8 |
| 10 | 6.92 | s | |
| 13 | 5.29 | d | 9.3 |
| 14a | 2.52 | ddd | 16.6, 8.7, 7.6 |
| 14b | 2.17 | o.m | |
| 16 | 1.12 | s | |
| 17 | 1.29 | s | |
| 18 | 1.94 | s | |
| 19 | 1.67 | s | |
| 20a | 4.93 | d | 12.9 |
| 20b | 4.55 | d | 12.9 |
| OAc | 2.21 | s | |
| OAc | 2.18 | s | |
| OAc | 2.09 | s | |
| OAc | 1.97 | s | |
| OAc | 1.96 | s | |
| 2' | 6.37 | d | 16.1 |
| 3' | 7.64 | d | 16.1 |
| o | 7.49 | m | |
| m,p | 7.38 | m |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 46.3 |
| 2 | 68.9 |
| 3 | 152.1 |
| 4 | 167.4 |
| 5 | 68.2 |
| 6a | 37.4 |
| 7 | 67.4 |
| 8 | 123.6 |
| 9 | 144.5 |
| 10 | 68 |
| 11 | 136.7 |
| 12 | 135.6 |
| 13 | 68.9 |
| 14a | 25.1 |
| 15 | 36.2 |
| 16 | 33.9 |
| 17 | 24.6 |
| 18 | 17 |
| 19 | 12.9 |
| 20a | 59.6 |
