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Table 1 1 H-NMR data of compounds 1-8 at 300 (compounds 2,3,4,5,7), 400 (compound 8) and 500 (compound 6) MHz; δ in ppm, J and W 1/2 in Hz

From: Biotransformation of oral contraceptive ethynodiol diacetate with microbial and plant cell cultures

COMPOUNDS
Carbon 1 2 3 4 5 6 7 8
1 1.41, 2.05 1.12, 2.07, 1.36, 1.70 1.38, 1.94 1.52, 2.24 1.54, 2.25 1.74, 1.96 1.75, 1.92
2 2.01, 2.27 dt, J=13.4, 2.8 1.33, 1.94 1.46, 2.01 1.55, 1.83 2.21, 2.38 2.28, 2.37 1.95, 2.23 1.91, 1.98
3 5.20 br s, W1/2=19.6 4.05, m (W1/2=17.4 Hz) 5.20, m (W1/2=22.8 Hz) 4.01, m (W1/2=15.6 Hz) - - 4.14 m, W1/2=16.8 5.85d J =9.6
4 5.32 5.55, br s (W1/2=9.7 Hz) 5.55, br s, (W1/2=17.2 Hz) 5.40, br s (W1/2=9.37 Hz) 5.81 s 5.81 s 5.37 5.50 d J=9.6
5 - - - - - - - -
6 0.95, 1.68 4.12, br s (W1/2=9.6 Hz) 4.16, br s, (W1/2=17.1 Hz) 2.05, 2.41 2.27, 2.49 2.29, 2.45 dt, J=14.5, 3.28 1.67, 1.82 1.77, 1.82
7 1.17, 1.80 2.05, 2.65 1.13, 1.87 0.90, 1.75 1.12, 1.83 1.06, 1.82 0.94, 1.73 1.15, 1.78
8 1.25 1.94 1.82 1.72 1.36 1.35 1.25 0.82
9 0.71 0.60 0.65 0.80 0.85 0.86 0.67 1.08
10 1.77 1.80 2.20 - 2.06 2.07 td, J=10.5, 4.7 1.75 1.47
11   1.25, 1.84 1.23, 1.85 1.59, 1.67 1.22, 1.91 1.23, 1.88 1.13, 2.02 0.78, 1.51
12 1.67, 1.82 1.65, 1.83 1.66, 1.84 1.66, 1.82 1.70, 1.87 1.63, 1.75 1.27, 2.04 1.54, 1.68
13 - - - - - - - -
14 1.51 1.50 1.52 1.48 1.54 1.51 1.50 1.42
15 1.31, 1.72 1.37, 1.67 1.27, 1.29 1.37, 1.72 1.33, 1.75 1.27, 1.54 1.32, 1.77 1.28, 1.67
16 1.98, 2.72 2.15, 2.65 2.04, 2.65 2.05, 2.65 1.97, 2.73 ddd, J=15, 9.6, 5.7 1.98, 2.27 1.99, 2.70 ddd J=15, 6.0, 3.6 1.94, 2.27
17 - - - - -   - -
18 0.87, s 0.94, s 0.95, s 0.93, s 0.91, s 0.89, s 0.87, s 0.84, s
20 - - - - - - - -
21 2.55, s 2.94, s 2.97, s 2.95, s 2.57, s 2.55, s 2.55, s 2.55, s
22 - - - - -   -  
23 2.02 2.01, s 2.00, s 1.99, s 2.02 s   2.01 s  
24         
25 2.02 2.01, s 2.00, s 1.99, s     
  1. Note: Assignments based on COSY, HMBC and HMQC spectra. Assignments shown without multiplicity means multiplet.