Dou et al.
FULL PAPER
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CH2), 2.80 (dd, J=6.8, 14.8 Hz, 1H, CH), 3.24 (dd, J=
8.4, 14.8 Hz, 1H, CH), 4.73 (t, J=7.6 Hz, 1H, CH),
7.04 (d, J=8.0 Hz, 2H, ArH), 7.29—7.24 (m, 4H, ArH),
7.41 (d, J=8.4 Hz, 2H, ArH), 9.80 (s, 1H, NH), 10.64
(s, 1H, OH); IR (KBr) ν: 3293, 3125, 3068, 1668, 1602,
1559, 1514, 1491, 1449, 1377, 1309, 1281, 1249, 1092,
921, 816, 780, 757, 723 cm - 1. HRMS calcd for
C24H2635ClNO3 434.1499 (M+Na), found 434.1505.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-N,3-di(p-tolyl)propanamide (5b) m.p. 221—
921, 83, 756, 718 cm
.
HRMS calcd for
C24H2679BrNO4 472.1123 (M+H), found 472.1118.
3-(4-Chlorophenyl)-3-(2-hydroxy-4,4-dimethyl-6-
oxocyclohex-1-enyl)-N-phenylpropanamide
(5f)
m.p. 215—217 ℃ (Lit.22 208—210 ℃); H NMR
(DMSO-d6, 400 MHz) δ: 0.93 (s, 6H, 2×CH3), 2.30—
2.05 (m, 4H, 2×CH2), 2.82 (dd, J=6.8, 14.8 Hz, 1H,
CH), 3.27 (dd, J=8.8, 14.8 Hz, 1H, CH), 4.74 (t, J=7.6
Hz, 1H, CH), 6.99 (t, J=7.2 Hz, 1H, ArH), 7.30—7.22
(m, 6H, ArH), 7.53 (d, J=8.4 Hz, 2H, ArH), 9.91 (s, 1H,
NH), 10.67 (s, 1H, OH); IR (KBr) ν: 3289, 3080, 1654,
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223 ℃ (Lit.22 218—220 ℃); H NMR (DMSO-d6,
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400 MHz) δ: 0.92 (s, 6H, 2×CH3), 2.35—2.00 (m, 10H,
2×CH3+2×CH2), 2.81 (dd, J=7.2, 14.8 Hz, 1H, CH),
3.21 (dd, J=8.4, 14.8 Hz, 1H, CH), 4.70 (t, J=7.6 Hz,
1H, CH), 6.98 (d, J=8.0 Hz, 2H, ArH), 7.04 (d, J=8.0
Hz, 2H, ArH), 7.15 (d, J=8.0 Hz, 2H, ArH), 7.42 (d,
J=8.0 Hz, 2H, ArH), 9.77 (s, 1H, NH), 10.48 (s, 1H,
OH); IR (KBr) ν: 3297, 3195, 3029, 1670, 1618, 1601,
1550, 1513, 1446, 1379, 1262, 1249, 1046, 983, 936,
816, 752, 718 cm- 1. HRMS calcd for C25H29NO3
392.2226 (M+H), found 392.2230.
1602, 1550, 1491, 1444, 1377, 1309, 1254, 1148, 1051,
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821, 755, 727, 691 cm 1. HRMS calcd for
C23H2435ClNO3 420.1343 (M+Na), found 420.1372.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-N-phenyl-3-p-tolylpropanamide (5g) m.p. 237
—239 ℃ (Lit.22 233—235 ℃); H NMR (DMSO-d6,
1
400 MHz) δ: 0.92 (s, 6H, 2×CH3), 2.05 (s, 2H, CH2),
2.20 (s, 3H, CH3), 2.28 (s, 2H, CH2), 2.82 (dd, J=6.8,
14.8 Hz, 1H, CH), 3.24 (dd, J=8.8, 14.8 Hz, 1H, CH),
4.71 (t, J=7.6 Hz, 1H, CH), 7.00—6.97 (m, 3H, ArH),
7.16 (d, J=8.0 Hz, 2H, ArH), 7.24 (t, J=7.6 Hz, 2H,
ArH), 7.54 (d, J=8.0 Hz, 2H, ArH), 9.87 (s, 1H, NH),
10.50 (s, 1H, OH); IR (KBr) ν: 3297, 3197, 3049, 1654,
1602, 1551, 1514, 1498, 1488, 1442, 1376, 1254, 1176,
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-3–(4-methoxyphenyl)-N-p-tolylpropanamide
1
(5c) m.p. 204—206 ℃; H NMR (DMSO-d6, 400
MHz) δ: 0.92 (s, 6H, 2×CH3), 2.04 (s, 2H, CH2), 2.22
(s, 3H, CH3), 2.33 (s, 2H, CH2), 2.81 (dd, J=6.8, 14.8
Hz, 1H, CH), 3.19 (dd, J=8.4, 14.8 Hz, 1H, CH), 3.69
(s, 3H, CH3O), 4.68 (t, J=7.6 Hz, 1H, CH), 6.75 (d, J=
8.4 Hz, 2H, ArH), 7.04 (d, J=8.4 Hz, 2H, ArH), 7.19 (d,
J=8.4 Hz, 2H, ArH), 7.42 (d, J=8.4 Hz, 2H, ArH),
9.76 (s, 1H, NH), 10.48 (s, 1H, OH); IR (KBr) ν: 3297,
3196, 3058, 1668, 1615, 1560, 1513, 1448, 1379, 1247,
1150, 829, 815 cm- 1. HRMS calcd for C25H29NO4
430.1995 (M+Na), found 430.2008.
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1116, 1095, 972, 795, 758, 723, 691 cm . HRMS calcd
for C24H27NO3 400.1889 (M+Na), found 400.1946.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-3-(3,4-dimethylphenyl)-N–phenylpropanamide
1
(5h) m.p. 218—220 ℃; H NMR (DMSO-d6, 400
MHz) δ: 0.93 (s, 6H, 2×CH3), 2.35—2.05 (m, 10H, 2
×CH3+2×CH2), 2.83 (dd, J=6.8, 14.8 Hz, 1H, CH),
3.22 (dd, J=8.4, 14.8 Hz, 1H, CH), 4.89 (t, J=7.6 Hz,
1H, CH), 6.92—6.99 (m, 3H, ArH), 7.04 (s, 1H, ArH),
7.24 (t, J=7.6 Hz, 2H, ArH), 7.56 (d, J=8.0 Hz, 2H,
ArH), 9.86 (s, 1H, NH), 10.47 (s, 1H, OH); IR (KBr) ν:
3279, 3139, 3053, 1641, 1597, 1558, 1499, 1485, 1456,
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-N–(4-methoxyphenyl)-3-p-tolylpropanamide
1
(5d) m.p. 227—229 ℃; H NMR (DMSO-d6, 400
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MHz) δ: 0.93 (s, 6H, 2×CH3), 2.05 (s, 2H, CH2), 2.21
(s, 3H, CH3), 2.35 (s, 2H, CH2), 2.79 (dd, J=7.2, 14.8
Hz, 1H, CH), 3.19 (dd, J=8.4, 14.8 Hz, 1H, CH), 3.69
(s, 3H, CH3O), 4.70 (t, J=7.6 Hz, 1H, CH), 6.82 (d, J=
8.8 Hz, 2H, ArH), 6.98 (d, J=8.0 Hz, 2H, ArH), 7.15 (d,
J=8.0 Hz, 2H, ArH), 7.44 (d, J=8.8 Hz, 2H, ArH),
9.71 (s, 1H, NH), 10.48 (s, 1H, OH); IR (KBr) ν: 3202,
3139, 3082, 1664, 1615, 1558, 1512, 1465, 1379, 1246,
1376, 1249, 1096, 971, 927, 891, 814, 749, 718 cm .
HRMS calcd for C25H29NO3 414.2045 (M+Na), found
414.2107.
3-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-
enyl)-3-(3,4-dimethoxyphenyl)-N–phenylpropan-
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amide (5i) m.p. 223—224 ℃; H NMR (DMSO-d6,
400 MHz) δ: 0.94 (s, 6H, 2×CH3), 2.07 (s, 2H, CH2),
2.34 (s, 2H, CH2), 2.83 (dd, J=6.8, 14.8 Hz, 1H, CH),
3.23 (dd, J=8.8, 14.8 Hz, 1H, CH), 3.66 (s, 3H, CH3O),
3.67 (s, 3H, CH3O), 4.70 (t, J=8.0 Hz, 1H, CH), 6.77 (s,
2H, ArH), 6.91 (s, 1H, ArH), 6.98 (t, J=7.6 Hz, 1H,
ArH), 7.24 (t, J=8.0 Hz, 2H, ArH), 7.55 (d, J=8.0 Hz,
2H, ArH), 9.88 (s, 1H, NH), 10.52 (s, 1H, OH); IR (KBr)
ν: 3275, 3136, 3089, 1640, 1612, 1555, 1517, 1501,
1489, 1465, 1455, 1381, 1269, 1229, 1048, 1025, 970,
850, 766, 701 cm- 1. HRMS calcd for C25H29NO5
446.1944 (M+Na), found 446.1972.
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1108, 923, 824, 792, 750, 717 cm . HRMS calcd for
C25H29NO4 430.1995 (M+Na), found 430.2037.
3-(4-Bromophenyl)-3-(2-hydroxy-4,4-dimethyl-6-
oxocyclohex-1-enyl)-N–(4-methoxyphenyl)propan-
1
amide (5e) m.p. 217—219 ℃; H NMR (DMSO-d6,
400 MHz) δ: 1.07 (s, 6H, 2×CH3), 2.15 (s, 2H, CH2),
2.35 (s, 2H, CH2), 2.92 (dd, J=6.8, 14.8 Hz, 1H, CH),
3.37 (dd, J=8.8, 14.8 Hz, 1H, CH), 3.84 (s, 3H, CH3O),
4.86 (t, J=7.6 Hz, 1H, CH), 6.97 (d, J=8.8 Hz, 2H,
ArH), 7.37 (d, J=8.4 Hz, 2H, ArH), 7.53 (d, J=8.0 Hz,
2H, ArH), 7.58 (d, J=8.8 Hz, 2H, ArH), 9.91 (s, 1H,
NH), 10.80 (s, 1H, OH); IR (KBr) ν: 3298, 3140, 3078,
1664, 1638, 1615, 1557, 1511, 1463, 1376, 1249, 1108,
N-(3-Chlorophenyl)-3-(4-chlorophenyl)-3-(2-
hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl) propan-
1
amide (5j) m.p. 237—238 ℃; H NMR (DMSO-d6,
400 MHz) δ: 0.92 (s, 6H, 2×CH3), 2.04 (s, 2H, CH2),
2370
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 2368— 2372