2204 J. Agric. Food Chem., Vol. 53, No. 6, 2005
Li et al.
Table 2. 1H NMR and IR Data of Compounds 2
compd
1H NMR,
1.69 (m, 2H), 1.86 2.05 (m, 2H), 2.53 (s, 3H), 2.81
11.9 Hz, J 2.7 Hz), 6.93 (d, 1H, J 5.2 Hz),
5.0 Hz), 8.50 (s, 1H), 12.53 (s, 1H)
1.40 (m, 14H), 1.65 1.71 (m, 2H), 1.86 2.07 (m, 2H), 2.81
2.9 Hz), 6.50 (s, 1H), 7.60 (s, 1H), 12.53 (s, 1H)
2.44 (m, 2H), 2.77 2.97 (m, 2H), 3.91 (s, 6H),
2.9 Hz), 5.79 (s, 1H), 7.42 (s, 1H), 12.51 (s, 1H)
2.49 (m, 2H), 2.45 (s, 6H), 2.80 2.98 (m, 2H),
2.9 Hz), 6.78 (s, 1H), 7.97 (s, 1H), 12.40 (s, 1H)
1.87 (m, 2H), 1.98 2.44 (m, 2H), 2.77 2.98 (m, 2H),
7.1 Hz), 4.87 (dd, 1H, J 11.7 Hz, J 2.9 Hz),
.73 (s, 1H), 7.33 (s, 1H), 12.49 (s, 1H)
7.5 Hz), 1.21 1.41 (m, 14H), 1.65
2.93 (m, 2H), 4.18 (t, 4H, J 6.6 Hz), 4.86 (dd, 1H, J
2.9 Hz), 5.75 (s, 1H), 7.32 (s, 1H), 12.51 (s, 1H)
1.41 (m, 26H), 1.66 1.89 (m, 2H), 1.97 2.44 (m, 2H), 2.72
11.8 Hz, J 2.9 Hz), 5.05
2.44 (s, 1H)
1.41 (m, 14H), 1.73
.58 (dd, 1H, J 11.2 Hz, J
8.3 Hz), 8.19 (s, 1H), 8.48 (s, 1H)
1.40 (m, 14H), 1.74 1.76 (m, 2H), 2.00
9.4 Hz), 6.82 6.87 (m, 2H), 7.25
δ
IR (ν
, cm-1)
2A
1
1.20
4
8
−
1.40 (m, 14H), 1.62
.88 (dd, 1H, J
.48 (d, 1H, J
−
−
−
2.98 (m, 2H),
3400, 3150, 3080, 2920, 2860, 1720,
1600, 1340, 1155
R
,
â
1
)
R
,
â
2
)
)
)
2A
2A
2A
2A
2
3
4
5
1.21−
−
−
−
2.92 (m, 2H), 3.98 (s, 3H),
3250, 3150, 3080, 2920, 2860,
1715, 1590, 1360, 1160
3200, 3150, 3030, 2920, 2860,
1720, 1610, 1360, 1150
3250, 3180, 2920, 2860, 1710,
1600, 1340, 1155
3350, 3220, 3150, 2920, 2860,
1720, 1700, 1610, 1340,
4
.82 (dd, 1H, J
1.42 (m, 14H), 1.63
.85 (dd, 1H, J
1.43 (m, 14H), 1.63
.88 (dd, 1H, J 11.9 Hz, J
1.41 (m, 20H), 1.66
.29 (q, 4H, J
R
,
â
1
)
)
11.7 Hz, J
−
11.6 Hz, J
−
R
,
,
â
2
2
)
)
1.21−
1.85 (m, 2H), 1.99
−
−
4
R,
â
1
R
â
1.22−
1.90 (m, 2H), 2.00
−
−
4
R,
â
1
)
R
,
â2
)
1.33−
−
−
−
)
4
5
)
R
,
â1
)
R
,
â
2
1160
2A
2A
2A
2A
6
7
8
9
1.02 (t, 6H, J
2
J
)
−
−1.87 (m, 6H), 2.00
−
2.44 (m, 2H),
11.8 Hz,
3150, 3090, 2920, 2860, 1735,
1710, 1605, 1350, 1150
.78
R,â2
)
−
)
R
,
â1
)
1.20−
−
−
−
2.99 (m, 2H), 4.89 (dd, 1H,
3240, 3180, 3060, 2920, 2860,
1720, 1700, 1610, 1360,
J
1
R
,
â1
)
R
,
â2
)
−5.11 (m, 2H), 5.66 (s, 1H), 7.26 (s, 1H),
1155
1.21−
−
1.75 (m, 2H), 2.04
−
2.46 (m, 2H), 2.31 (s, 3H), 2.65
2.9 Hz), 7.12 (d, 2H, J
−2.98 (m, 2H),
3350, 3150, 3030, 2920, 2860,
1710, 1695, 1610, 1345,
4
J
R,
â
1
)
R
,
â2
)
)
8.3 Hz), 7.27 (d, 2H,
)
1140
1.21−
−
−
2.44 (m, 2H), 2.65
−
2.98 (m, 2H), 3.79 (s, 3H),
7.30 (m, 2H), 8.12 (s, 1H),
3350, 3160, 3060, 2920, 2860,
1710, 1690, 1610, 1350,
4
.57 (d, 1H, J
)
−
−
8.69 (s, 1H)
1140
2
A
A
10
11
1.24
−
1.43 (m, 14H), 1.72
11.1 Hz, J
1.42 (m, 14H), 1.73
11.3 Hz, J
7.40 (m, 1H), 8.13
1.77 (m, 38H), 1.97 2.01 (m, 1H), 2.31
.86 2.94 (m, 1H), 3.86 (s, 1H), 4.08 4.21 (m, 2H), 4.41 (dd, 1H, J
2.0 Hz), 6.32 (d, 1H, J 8.6 Hz), 8.31 (s, 1H)
1.43 (m, 14H), 1.70 1.76 (m, 2H), 2.03 2.43 (m, 2H), 2.64
.56 (dd, 1H, J 11.1 Hz, J 3.2 Hz), 6.99 7.06 (m, 2H), 7.33
.27 (s, 1H), 8.37 (s, 1H)
1.41 (m, 14H), 1.65 1.89 (m, 2H), 1.99
.04 (dd, 1H, J 11.7 Hz, J 3.0 Hz), 7.43 (dd, 1H, J
.53 (d, 1H, J 8.8 Hz), 7.86 (d, 1H, J 2.5 Hz), 8.66 (s, 1H), 9.70 (s, 1H)
1.42 (m, 14H), 1.73 1.80 (m, 2H), 2.02 2.46 (m, 2H), 2.65 3.02 (m, 2H),
.54 (dd, 1H, J 11.2 Hz, J 3.2 Hz), 7.06 (dd, 1H, J 8.6, 2.5 Hz),
.31 (d, 1H, J 8.6 Hz), 8.26 (d, 1H, J 2.5 Hz), 8.14 (s, 1H), 8.96 (s, 1H)
1.43 (m, 14H), 1.74 1.76 (m, 2H), 2.04 2.40 (m, 2H), 2.34 (s, 3H), 2.68
.55 (dd, 1H, J 11.1 Hz, J 2.8 Hz), 6.95 6.98 (m, 1H), 7.21 7.22 (m, 3H),
.10 (s, 1H), 8.24 (s, 1H)
1.42 (m, 14H), 1.70 1.77 (m, 2H), 1.99
.29 (s, 3H), 2.33 2.45 (m, 1H), 2.66 2.97 (m, 2H), 4.55 (dd, 1H, J
2.4 Hz), 7.01 (d, 2H, J 5.5 Hz), 7.53 (s, 1H), 8.11 (s, 1H), 8.50 (s, 1H)
1.42 (m, 14H), 1.68 2.03 (m, 2H), 2.04 2.37 (m, 2H), 2.67 3.05 (m, 2H),
.04 (dd, 1H, J 11.7 Hz, J 3.0 Hz), 7.61 7.66 (m, 1H), 7.83 7.87 (m, 1H),
.95 7.99 (m, 1H), 8.54 8.56 (m, 1H), 8.89 (s, 1H), 9.80 (s, 1H)
1.42 (m, 14H), 1.67 2.03 (m, 2H), 2.04 2.36 (m, 2H), 2.66 3.04 (m, 2H),
3.0 Hz), 7.11 7.72 (m, 4H), 8.63 (s, 1H),
−
1.76 (m, 2H), 2.03
3.1 Hz), 7.26 7.37 (m, 4H), 8.24 (s, 1H), 8.33 (s, 1H)
1.79 (m, 2H), 2.05 2.46 (m, 2H), 2.66 3.01 (m, 2H), 4.53 (dd, 1H,
3.2 Hz), 7.05 7.11 (m, 1H), 7.28 7.31 (m, 1H),
8.16 (m, 1H), 7.95 (s, 1H), 8.88 (s, 1H)
2.40 (m, 3H), 2.71 2.75 (m, 1H),
11.2 Hz,
−
2.42 (m, 2H), 2.63
−
2.98 (m, 2H), 4.55 (dd, 1H,
3350, 3210, 2920, 2850, 1725,
1705, 1600, 1335, 1150
3300, 3150, 3050, 2920, 2860,
1720, 1700, 1600, 1355,
J
R
,
â
1
)
R
,
â
2
)
−
2
1.22−
−
−
−
J
7
R
,
â
1
)
−
R
,
â
2
)
−
−
.37
−
1140
2A
2A
2A
2A
2A
2A
2A
2A
2A
2B
12
13
14
15
16
17
18
19
20
1
1.23−
−
−
−
3300, 3250, 2920, 2860, 1730,
1705, 1690, 1530, 1340,
1155
3350, 3250, 3080, 2920, 2860,
1720, 1710, 1620, 1330,
1150
2
J
−
)
−
R
,
â1
)
R
,
â
2
)
1.22−
−
−
−2.98 (m, 2H),
4
8
R
,
â
1
)
R
,
â2
)
−
−7.38 (m, 2H),
1.21−
−
−2.36 (m, 2H), 2.65−3.03 (m, 2H),
3290, 3200, 2920, 2860, 1708,
1580, 1340, 1148
5
7
R,
â
1
)
R
,
â2
)
)
8.8 Hz, 2.5 Hz),
)
)
−
1.22−
−
−
3300, 3150, 3080, 2920, 2860,
1715, 1695, 1595, 1360,
1140
3350, 3180, 2920, 2860, 1710,
1670, 1615, 1340, 1150
4
7
R,
â
1
)
R
,
â2
)
)
)
)
−
1.22−
−
−2.97 (m, 2H),
4
8
R,
â
1
)
R
,
â2
)
−
−
1.21−
−
−2.07 (m, 1H), 2.20 (s, 3H),
3350, 3150, 3050, 2920, 2860,
1710, 1695, 1605, 1345,
1140
3300, 3260, 2920, 2860, 1710,
1605, 1350, 1160
2
J
−
−
R,â1
) 11.4 Hz,
R
,
â
2
)
)
1.22−
−
−
−
5
7
R,
â
1
)
R
,
â2
)
−
−
−
−
1.22−
−
−
−
3350, 3250, 3080, 2920, 2860,
1720, 1710, 1600, 1335,
1150
3370, 3250, 3080, 2920, 2860,
1720, 1680, 1600, 1340,
5
9
.05 (dd, 1H, J
.68 (s, 1H)
1.43 (m, 14H), 1.73
.61 (dd, 1H, J
R,
â
1
)
11.7 Hz, J
R
,
â
2
2
)
−
1.23−
−1.76 (m, 2H), 2.06
−
2.39 (m, 2H), 2.59 (s, 3H), 2.66
3.1 Hz), 7.54 (d, 2H, J 8.7 Hz), 7.95 (d, 2H,
−
2.99 (m, 2H),
4
J
R,
â
1
)
11.1 Hz, J
R
,
â
)
)
)
8.7 Hz), 8.39 (s, 1H), 8.56 (s, 1H)
1.53 (m, 3H), 1.89 1.93 (m, 2H), 2.03
2.86 (m, 1H), 4.60 (dd, 1H, J
8.6, 2.2 Hz), 7.50 (d, 1H, J 8.6 Hz), 8.33 (d, 1H, J
1150
1.46−
−
−2.12 (m, 2H), 2.50−2.58 (m, 2H),
3200, 3150, 2800, 1700, 1680,
1580, 1345, 1150
2
J
9
.76
)
−
R
,
â1
)
11.2 Hz, J 4.8 Hz), 7.17 (dd, 1H,
R
,
â
2
)
)
)
2.5 Hz), 8.58 (s, 1H),
.89 (s, 1H)
1.59 (m, 3H), 1.91
.47 2.56 (m, 1H), 2.60
.55 (s, 1H), 8.04 (s, 1H), 8.36 (s, 1H)
1.52 (m, 3H), 1.93 1.97 (m, 2H), 2.07
.77
.78 (s, 1H), 7.51 (s, 1H), 12.48 (s, 1H)
1.45 (m, 3H), 1.79 2.03 (m, 4H), 2.29
2.76 (m, 1H), 4.56 (dd, 1H, J
7.48 (m, 2H), 9.00 (s, 1H), 9.98 (s, 1H)
2B
2B
2B
2
3
4
1.39−
−1.98 (m, 2H), 2.02
−2.10 (m, 2H), 2.20 (s, 3H), 2.28 (s, 3H),
3320, 3200, 3080, 2920, 2880,
1700, 1665, 1600, 1330,
1140
3250, 3200, 3100, 3020, 2920,
2850, 1720, 1620, 1340,
2
7
−
−2.76 (m, 2H), 4.38−4.40 (d, 1H, J
)
7.4 Hz), 6.99 (s, 2H),
1.35−
−
−2.19 (m, 2H), 2.53−2.61 (m, 2H),
2
5
−
2.85 (m, 1H), 3.90 (s, 6H), 4.56 (dd, 1H, J
R,
â1
)
11.5 Hz, J
R
,
â2
)
4.7 Hz),
1150
1.27−
−
−2.37 (m, 1H), 2.46−2.52 (m, 1H),
3380, 3200, 2920, 2880, 1710,
1600, 1320, 1140
2
7
.67
.43
−
−
R
,
â1
)
11.2 Hz, J 4.9 Hz), 7.34
R
,
â
2
)
−7.39 (m, 2H),