Molecules 2015, 20
6989
7-((3-Bromobenzyl)oxy)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4H-chromen-4-one (3j). Yield 47%.
1
m.p. 234–236 °C; H-NMR (DMSO-d6) δ 12.52 (s, 1H, -OH), 9.68 (brs, 1H, -OH), 9.55 (brs, 1H,
-OH), 9.33 (s, 1H, -OH), 7.72 (d, J = 2.4 Hz, 1H, -ArH), 7.69 (s, 1H, -ArH), 7.56 (dd, J = 8.4, 2.0 Hz,
2H, -ArH), 7.49 (d, J = 8.0 Hz, 1H, -ArH), 7.39 (t, J = 8.0 Hz, 1H, -ArH), 6.90 (d, J = 8.8 Hz, 1H,
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-ArH), 6.81 (d, J = 2.0 Hz, 1H, -ArH), 6.46 (d, J = 2.0 Hz, 1H, -ArH), 5.25 (s, 2H, -CH2); C-NMR
(DMSO-d6) δ 176.4, 164.1, 160.9, 156.4, 148.3, 147.8, 145.5, 139.5, 136.5, 131.4, 131.3, 130.8, 127.2,
122.3, 122.2, 120.5, 116.0, 115.7, 104.7, 98.5, 93.3, 69.4; ESI-MS (m/z): 471.0, 473.0 [M+H]+.
2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-7-((3-methylbenzyl)oxy)-4H-chromen-4-one (3k). Yield 43%.
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m.p. 224–226 °C; H-NMR (DMSO-d6) δ 12.51 (s, 1H, -OH), 9.63 (brs, 1H, -OH), 9.53 (brs, 1H,
-OH), 9.33 (brs, 1H, -OH), 7.73 (d, J = 2.0 Hz, 1H, -ArH), 7.57 (d, J = 8.8, 2.0 Hz, 1H, -ArH),
7.16–7.32 (m, 4H, -ArH), 6.90 (d, J = 8.8 Hz, 1H, -ArH), 6.79 (d, J = 2.0 Hz, 1H, -ArH), 6.43 (d,
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J = 2.0 Hz, 1H, -ArH), 5.19 (s, 2H, -CH2), 2.33 (s, 3H, -CH3); C-NMR (DMSO-d6) δ 176.4, 164.4,
160.9, 156.4, 148.3, 147.8, 145.5, 138.2, 136.6, 136.5, 129.2, 128.9, 128.9, 125.4, 122.3, 120.5, 116.0,
115.7, 104.6, 98.5, 93.2, 70.5, 21.5; ESI-MS (m/z): 407.0 [M+H]+.
3-(((2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl)oxy)methyl)benzonitrile (3l). Yield
1
42%. m.p. 246–247 °C; H-NMR (DMSO-d6) δ 12.52 (s, 1H, -OH), 9.66 (s, 1H, -OH), 9.53 (s, 1H,
-OH), 9.31 (s, 1H, -OH), 7.96 (brs, 1H, -ArH), 7.82–7.86 (m, 2H, -ArH), 7.72 (d, J = 2.0 Hz, 1H,
-ArH), 7.63–7.67 (m, 1H, -ArH), 7.56 (dd, J = 8.4, 2.0 Hz, 1H, -ArH), 6.90 (d, J = 8.4 Hz, 1H, -ArH),
6.83 (d, J = 1.6 Hz, 1H, -ArH), 6.47 (d, J = 1.6 Hz, 1H, -ArH), 5.31 (s, 2H, -CH2); ESI-MS (m/z):
418.1 [M+H]+, 440.0 [M+Na]+.
2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-7-((3-nitrobenzyl)oxy)-4H-chromen-4-one (3m). Yield 46%.
m.p. 264–266 °C; 1H-NMR (DMSO-d6) δ 12.53 (s, 1H, -OH), 9.67 (s, 1H, -OH), 9.54 (brs, 1H, -OH),
9.31 (s, 1H, -OH), 8.35 (s, 1H, -ArH), 8.23 (dd, J = 8.4, 1.6 Hz, 1H, -ArH), 7.94 (d, J = 8.0 Hz, 1H,
-ArH), 7.72–7.76 (m, 2H, -ArH), 7.56 (dd, J = 8.4, 2.0 Hz, 1H, -ArH), 6.90 (d, J = 8.4 Hz, 1H, -ArH),
6.85 (d, J = 2.4 Hz, 1H, -ArH), 6.49 (d, J = 2.4 Hz, 1H, -ArH), 5.41 (s, 2H, -CH2); 13C-NMR
(DMSO-d6) δ 175.9, 163.4, 160.5, 155.9, 147.8, 147.4, 145.1, 138.6, 136.1, 134.2, 130.2, 123.0, 122.2,
121.8, 120.0, 115.5, 115.2, 104.3, 98.0, 92.9, 68.5; ESI-MS (m/z): 438.1 [M+H]+.
2-(3,4-Dihydroxyphenyl)-7-((4-fluorobenzyl)oxy)-3,5-dihydroxy-4H-chromen-4-one (3n). Yield 50%.
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m.p.254–255 °C; H-NMR (DMSO-d6) δ 12.51 (s, 1H, -OH), 9.68 (s, 1H, -OH), 9.53 (brs, 1H, -OH),
9.33 (s, 1H, -OH) 7.72 (d, J = 2.0 Hz, 1H, -ArH), 7.52–7.58 (m, 3H, -ArH), 7.27 (d, J = 8.8 Hz, 1H, -ArH),
7.24 (d, J = 8.8 Hz, 1H, -ArH), 6.90 (d, J = 8.4 Hz, 1H, -ArH), 6.81 (d, J = 2.4 Hz, 1H, -ArH), 6.43
(d, J = 2.4 Hz, 1H, -ArH), 5.22 (s, 2H, -CH2); 13C-NMR (DMSO-d6) δ 175.9, 163.7, 161.8 (d,
JC-F = 244.4 Hz), 160.0, 155.9, 147.8, 147.3, 145.0, 136.0, 132.4 (d, JC-F = 2.9 Hz), 130.2 (d,
JC-F = 8.3 Hz, 2C), 121.8, 120.0, 115.5, 115.4(d, J = 21.4 Hz, 2C), 115.2, 104.1, 98.0, 92.7, 69.2;
ESI-MS (m/z): 411.1 [M+H]+.
7-((4-Chlorobenzyl)oxy)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4H-chromen-4-one (3o). Yield 41%.
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m.p. 266–267 °C; H-NMR (DMSO-d6) δ 12.51 (s, 1H, -OH), 9.67 (s, 1H, -OH), 9.53 (s, 1H, -OH),
9.32 (s, 1H, -OH), 7.71 (d, J = 2.0 Hz, 1H, -ArH), 7.56 (dd, J = 8.4, 2.0 Hz, 1H, -ArH), 7.47–7.52 (m,