1256
C.-F. XIAO ET AL.
Compound 7f, 7-hydroxy-3-(3’,5’-dimethoxyphenyl) coumarin. IR (KBr)
(T%): 3284 (36), 2958 (58), 2836 (61), 1697 (27), 1598 (26), 1571 (35), 1508 (46), 1457
(49), 1425 (56), 1346 (45), 1303 (31), 1259 (57), 1234 (56), 1199 (38), 1157 (28), 1128
1
(46), 1064 (58), 1010 (52), 952 (72), 925 (68); H NMR (400 MHz,CD3COCD3) d:
3.80 (s, 6H, 30,50-OCH3), 6.49 (t, 1H, J ¼ 2.0 Hz, 40-ArH), 6.77 (d, 1H, J ¼ 2.4 Hz,
8-H), 6.85 (dd, 1H, J1 ¼ 8.4 Hz, J2 ¼ 2.4 Hz, 6-H), 6.90 (d, 2H, J ¼ 2.4 Hz, 20,60-ArH),
7.56 (d, 1H, J ¼ 8.4 Hz, 5-H), 8.07 (s, 1H, 4-H); 13C NMR (400 MHz, CD3COCD3)
d: 55.7, 100.8, 102.8, 107.5, 113.5, 114.0, 124.1, 130.7, 138.2, 141.5, 156.3, 160.6,
161.6, 161.9; EIMS m=z: 298 (Mþ), 269.
Compound 7g, 7-hydroxy-3-(3’,5’-dihydroxyphenyl) coumarin. IR (KBr)
(T%): 3168 (W, 18), 2362 (35), 1683 (16), 1616 (12), 1571 (16), 1509 (24), 1469 (26),
1380 (34), 1326 (20), 1301 (18), 1241 (29), 1201 (27), 1160 (15), 1133 (22), 1031 (40),
1
1002 (33), 931 (42), 887 (40), 840 (28); H NMR (400 MHz, CD3COCD3) d: 6.36 (t,
1H, J ¼ 2.4 Hz, 40-ArH), 6.70 (d, 2H, J ¼ 2.4 Hz, 20,60-ArH), 6.75 (d, 1H, J ¼ 2.0 Hz,
8-H), 6.85 (dd, 1H, J1 ¼ 8.4 Hz, J2 ¼ 2.0 Hz, 6-H), 7.55 (d, 1H, J ¼ 8.4 Hz, 5-H), 7.93
(s, 1H, 4-H); 13CNMR (400 MHz, CD3COCD3) d: 102.7, 103.3, 107.9, 113.4, 114.0,
124.3, 130.6, 138.1, 1411.0, 156.1, 159.1, 160.7, 161.8; ESIMS m=z: 270.3 (Mþ), 269.2
(Mþ-H).
Compound 7h, 5,7-dihydroxy-3-(3’,5’-dihydroxyphenyl) coumarin. IR
(KBr) (T%): 3259 (w, 26), 1691 (24), 1612 (20), 1519 (39), 1482 (35), 1413 (33),
1344 (29), 1294 (31), 1253 (37), 1209 (35), 1157 (23), 1083 (37), 1039 (46), 1004
(38), 943 (51), 892 (49); 1H NMR (400 MHz, CD3COCD3) d: 6.30(d, 1H, J ¼ 2.0 Hz,
40-ArH), 6.35(d, 1H, J ¼ 2.4 Hz, 6-H), 6.37(d, 1H, J ¼ 2.4 Hz, 8-H), 6.74 (d, 2H,
J ¼ 2.0 Hz, 20,60-ArH), 8.09 (s, 1H, 4-H), 8.30(s, 2H, 30,50-OH), 9.32 (s, 1H, 5-OH),
9.63 (s, 1H, 7-OH); 13CNMR (400 MHz, CD3COCD3) d: 95.0, 99.1, 99.2, 103.7,
107.8, 108.2, 113.7, 117.2, 120.4, 122.0, 135.3, 135.8, 138.5, 156.7, 157.1, 159.1,
160.8, 162.6; ESIMS m=z: 286.2 (Mþ), 285.2 (Mþ-H), 269.2.
Compound 7i, 7,8-dihydroxy-3-(3’,5’-dihydroxyphenyl) coumarin. IR
(KBr) (T%): 3208 (W, 29), 1695 (26), 1612 (25), 1517 (48), 1467 (36), 1402 (49),
1351 (33), 1295 (41), 1263 (41), 1207 (42), 1157 (35), 1120 (43), 1083 (55), 1054
1
(49), 1004 (51), 943 (65), 836 (53); H NMR (400 MHz, CD3COCD3) d: 6.36 (t,
1H, J ¼ 2.0 Hz, 40-ArH), 6.69 (d, 2H, J ¼ 2.0 Hz, 20,60-ArH), 6.87 (d, 1H, J ¼ 8.4 Hz,
5-H), 7.10 (d, 1H, J ¼ 8.4 Hz, 6-H), 7.91 (s, 1H, 4-H); 13C NMR (400 MHz,
CD3COCD3) d: 103.3, 107.9, 113.4, 114.1, 120.2, 124.2, 132.4, 138.2, 141.6, 143.9,
149.8, 159.1, 160.3; ESIMS m=z: 286.2 (Mþ), 285.2 (Mþ-H).
Compound 7j, 7-methoxy-8-hydroxy-3-(3’,5’-dihydroxyphenyl) coumarin.
IR (KBr) (T%): 3558 (35), 3486 (33), 3261 (W, 24), 2842 (39), 1679 (22), 1604 (18),
1508 (33), 1446 (26), 1394 (40), 1342 (28), 1284 (24), 1203 (34), 1155 (28), 1126 (27),
1103 (36), 1074 (31), 1004 (37), 946 (50), 852 (41); 1H NMR (400 MHz, CD3COCD3)
d: 3.95 (s, 3H, 7-OCH3), 6.38 (t, 1H, J ¼ 2.0 Hz, 40-ArH), 6.73 (d, 2H, J ¼ 2.0 Hz,
20,60-ArH), 7.03 (d, 1H, J ¼ 8.8 Hz, 6-H), 7.20 (d, 1H, J ¼ 8.8 Hz, 5-H), 7.94 (s, 1H,
4-H), 8.33 (s, 2H, 30,50-OH), 8.34 (s, 1H, 8-OH); 13CNMR (400 MHz, CD3COCD3)
d: 55.8, 103.4, 108.0, 109.2, 115.2, 119.5, 125.2, 134.2, 138.1, 141.2, 142.9, 151.1,
159.1, 160.3; ESIMS m=z: 300.1 (Mþ), 299.0 (Mþ-H), 284.1 (Mþ-H-CH3).