Spektraris NMR
2,9,10,13-Tetraacetyl-20-cinnamoyloxytaxa-4(5),11(12)-diene
Common Name: 2,9,10,13-Tetraacetyl-20-cinnamoyloxytaxa-4(5),11(12)-diene
Synonyms: 2α,9α,10β,13α-Tetraacetoxy-20-cinnamoyloxy-taxa-4(5),11(12)-diene
CAS Registry Number: 284672-77-1
InChI: InChI=1S/C37H46O10/c1-21-29(44-22(2)38)19-28-33(45-23(3)39)32-27(20-43-30(42)17-16-26-13-10-9-11-14-26)15-12-18-37(32,8)35(47-25(5)41)34(46-24(4)40)31(21)36(28,6)7/h9-11,13-17,28-29,32-35H,12,18-20H2,1-8H3/b17-16+/t28-,29-,32-,33+,34+,35-,37+/m0/s1
InChIKey: InChIKey=CCHLPDSWJHJSRB-LAGURDHDSA-N
Formula: C37H46O10
Molecular Weight: 650.76
Exact Mass: 650.3091
NMR Solvent: CDCl3
MHz: Not mentioned
Calibration: Not mentioned
NMR references: Zhang, J., Sauriol, F., Mamer, O., and Zamir, L.O. (2000). New Taxanes from the Needles of Taxus canadensis. J. Nat. Prod. 63, 929–933.
Species: Taxus
Notes: Proton signal at position 5 (5.79 ppm) was reported as a multiplet with a coupling constant of 3.4 Hz. Therefore we left peak shape and coupling constant blank in our table for proton 5. Carbon assignment missing for position 4 and acetate carbonyl carbons.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 1 | 1.79 | br d | 8.5 |
| 2 | 5.56 | br d | 4 |
| 3 | 3.35 | m | |
| 5 | 5.79 | ||
| 6 | 2.12 | m | |
| 7a | 2.01 | m | |
| 7b | 1.42 | dt | 11.9, 6.9 |
| 9 | 5.94 | d | 10.7 |
| 10 | 5.91 | d | 10.7 |
| 13 | 5.61 | br d | 10.1 |
| 14a | 2.78 | ddd | 16.1, 10.1, 8.5 |
| 14b | 1.88 | dd | 16.1, 3.5 |
| 16 | 1.03 | s | |
| 17 | 1.76 | s | |
| 18 | 1.97 | s | |
| 19 | 0.96 | s | |
| 20a | 4.98 | d | 14 |
| 20b | 4.78 | d | 14 |
| OAc | 2.09 | s | |
| OAc | 2.06 | s | |
| OAc | 2.06 | s | |
| OAc | 2.01 | s | |
| OCinn CH=α | 6.46 | d | 16 |
| OCinn CH=β | 7.7 | d | 16 |
| Ph-o | 7.53 | m | |
| Ph-m | 7.38 | m | |
| Ph-p | 7.38 | m |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 46.1 |
| 2 | 71.9 |
| 3 | 44.4 |
| 5 | 125.1 |
| 6 | 22.5 |
| 7 | 28.2 |
| 8 | 42 |
| 9 | 76.1 |
| 10 | 72.2 |
| 11 | 135.8 |
| 12 | 137.9 |
| 13 | 69.1 |
| 14 | 28.9 |
| 15 | 38 |
| 16 | 33 |
| 17 | 25.5 |
| 18 | 15.6 |
| 19 | 17.6 |
| 20 | 67 |
| OAc | 20.9 |
| OAc | 20.9 |
| OAc | 21.7 |
| OAc | 21.1 |
| OCinn C=O | 166.6 |
| OCinn CH=α | 117.8 |
| OCinn CH=β | 144.8 |
| Ph-1 | 134.4 |
| Ph-o | 128.1 |
| Ph-m | 129.1 |
| Ph-p | 130.3 |
