Organic & Biomolecular Chemistry
Paper
1319, 1305, 1262, 1240, 1014, 913, 802, 760, 641, 627 cm−1
.
1083, 925, 843, 750, 668, 627 cm−1. HRMS (ESI-TOF) m/z calcd
HRMS (ESI-TOF) m/z calcd for C15H11O2 [M + H]+: 223.0754, for C15H9ClNaO2 [M + H]+: 279.0183, found 279.0207.
found 223.0772.
7-Fluoro-3-phenyl-1H-isochromen-1-one
6-Methyl-3-phenyl-1H-isochromen-1-one (2g).7f Purified
(2b).7f
Purified using ethyl acetate and petroleum ether (v/v = 1 : 18) as the
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using ethyl acetate and petroleum ether (v/v = 1 : 20) as the eluent. Yield: 81% (96 mg). Light yellow oil. H NMR (CDCl3,
eluent. Yield: 71% (85 mg). Light yellow oil.1H NMR (CDCl3, 400 MHz): δ 8.15 (d, J = 8.0 Hz, 1H), 7.85–7.82 (m, 2H),
400 MHz): δ 7.98 (d, J = 8.4, 1H), 7.88–7.86 (m, 2H), 7.54–7.42 7.46–7.39 (m, 2H), 7.28–7.24 (m, 2H), 6.85 (s, 1H), 2.45 (s, 3H);
(m, 5H), 6.95 (s, 1H); 13C{1H} NMR (101 MHz, CDCl3) δ 161.9 13C{1H} NMR (101 MHz, CDCl3) δ 162.3, 153.5, 145.9, 137.5,
(d, JC–F = 248.5 Hz), 161.5, 153.2 (d, JC–F = 2.8 Hz), 134.1 (d, JC–F 132.0, 129.8, 129.53, 129.51, 128.8, 125.9, 125.1, 118.1, 101.7,
= 2.8 Hz), 131.7, 130.1, 128.9, 128.2 (d, JC–F = 7.7 Hz), 125.2, 21.9; IR (KBr): ν 3057, 3025, 2987, 1743, 1635, 1610, 1538,
123.4 (d, JC–F = 23.1 Hz), 122.2 (d, JC–F = 8.0 Hz), 115.3 (d, JC–F
=
1439, 1348, 1310, 1301, 1289, 1278, 1154, 1042, 985, 842, 764,
23.2 Hz), 101.0; IR (KBr): ν 3043, 3005, 1750, 1632, 1600, 1542, 688, 672 cm−1. HRMS (ESI-TOF) m/z calcd for C16H13O2 [M +
1483, 1362, 1320, 1300, 1279, 1262, 1101, 1083, 925, 843, 750, H]+: 237.0910, found 237.0958.
668, 627 cm−1. HRMS (ESI-TOF) m/z calcd for C15H10FO2 [M +
6,7-Dimethoxy-3-phenyl-1H-isochromen-1-one (2h).8a Purified
H]+: 241.0659, found 241.0679.
using ethyl acetate and petroleum ether (v/v = 1 : 10) as the
7-Methyl-3-phenyl-1H-isochromen-1-one (2c).7f Purified eluent. Yield: 85% (120 mg). Light yellow oil. H NMR (CDCl3,
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using ethyl acetate and petroleum ether (v/v = 1 : 23) as the 400 MHz): δ 7.89–7.86 (m, 2H), 7.70–7.69 (m, 1H), 7.49–7.40
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eluent. Yield: 76% (90 mg). Light yellow oil. H NMR (CDCl3, (m, 3H), 6.92 (s, 1H), 6.89 (s, 1H), 4.03 (s, 3H), 4.01 (s, 3H); 13
C
400 MHz): δ 8.06 (s, 1H), 7.83–7.80 (m, 2H), 7.48 (dd, J = 8.0, {1H} NMR (101 MHz, CDCl3) δ 162.3, 155.2, 152.7, 149.8, 135.2,
2.0 Hz, 1H), 7.44–7.38 (m, 3H), 7.35 (d, J = 8.0 Hz, 1H), 6.87 (s, 132.2, 129.7, 128.8, 125.0, 113.8, 109.5, 106.5, 101.6, 56.4, 56.3;
1H), 2.42 (s, 3H); 13C{1H} NMR (101 MHz, CDCl3) δ 162.5, IR (KBr): ν 3043, 3021, 2963, 1772, 1663, 1642, 1531, 1430,
152.8, 138.5, 136.2, 135.1, 132.1, 129.8, 129.4, 128.8, 125.9, 1357, 1363, 1321, 1249, 1201, 1132, 1011, 943, 884, 738, 693,
125.1, 120.4, 101.8, 21.4; IR (KBr): ν 3052, 3011, 2920, 1732, 613 cm−1. HRMS (ESI-TOF) m/z calcd for C17H15O4 [M + H]+:
1685, 1610, 1535, 1442, 1355, 1300, 1292, 1250, 1203, 1165, 283.0965, found 283.0998.
1077, 973, 831, 783, 685, 633 cm−1. HRMS (ESI-TOF) m/z calcd
5-Fluoro-3-phenyl-1H-isochromen-1-one (2i). Purified using
ethyl acetate and petroleum ether (v/v = 1 : 20) as the eluent.
for C16H13O2 [M + H]+: 237.0910, found 237.0947.
7-Methoxy-3-phenyl-1H-isochromen-1-one (2d).7f Purified Yield: 73% (88 mg). Light yellow oil. 1H NMR (CDCl3,
using ethyl acetate and petroleum ether (v/v = 1 : 12) as the 400 MHz): δ 8.14–8.09 (m, 1H), 7.93–7.89 (m, 2H), 7.51–7.42
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eluent. Yield: 86% (108 mg). Light yellow oil. H NMR (CDCl3, (m, 5H), 7.18 (s, 1H); 13C{1H} NMR (101 MHz, CDCl3) δ 166.7
400 MHz): δ 7.86–7.82 (m, 2H), 7.69 (d, J = 2.0 Hz, 1H), (d, JC–F = 255.2 Hz), 161.4, 154.9, 140.2 (d, JC–F = 10.9 Hz),
7.45–7.38 (m, 4H), 7.28 (dd, J = 8.4, 2.8 Hz, 1H), 6.91 (s, 1H), 133.0 (d, JC–F = 10.4 Hz), 131.5, 130.4, 128.9, 125.4, 117.0 (d,
3.90 (s, 3H); 13C{1H} NMR (101 MHz, CDCl3) δ 162.4, 159.5, JC–F = 1.4 Hz), 116.5 (d, JC–F = 23.2 Hz), 111.5 (d, JC–F = 22.5
151.6, 132.0, 131.1, 129.5, 128.7, 127.5, 124.9, 124.7, 121.6, Hz), 101.2 (d, JC–F = 2.7 Hz); IR (KBr): ν 3045, 3025, 1753, 1671,
109.9, 101.5, 55.7; IR (KBr): ν 3081, 3033, 2980, 1723, 1633, 1620, 1551, 1462, 1371, 1321, 1311, 1287, 1261, 1131, 1098,
1605, 1538, 1466, 1387, 1365, 1321, 1293, 1267, 1135, 1070, 901, 849, 787, 689, 632 cm−1. HRMS (ESI-TOF) m/z calcd for
945, 873, 735, 638, 601 cm−1. HRMS (ESI-TOF) m/z calcd for C15H10FO2 [M + H]+: 241.0659, found 241.0684.
C16H13O3 [M + H]+: 253.0859, found 253.0874.
3-Phenyl-6-(trifluoromethyl)-1H-isochromen-1-one
Purified using ethyl acetate and petroleum ether (v/v = 1 : 10) eluent. Yield: 82% (104 mg). Light yellow oil. H NMR (CDCl3,
as the eluent. Yield: 77% (112 mg). Light yellow oil. H NMR 400 MHz): δ 8.28 (d, J = 8.0 Hz, 1H), 7.79 (d, J = 8.4 Hz, 2H),
3-(4-Chlorophenyl)-1H-isochromen-1-one (2j).7f Purified
(2e).7f using ethyl acetate and petroleum ether (v/v = 1 : 20) as the
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(CDCl3, 400 MHz): δ 8.57 (s, 1H), 7.93–7.87 (m, 3H), 7.62 (d, J = 7.70 (t, J = 7.6 Hz, 1H), 7.55–7.47 (m, 2H), 7.41 (d, J = 8.4 Hz,
8.0 Hz, 1H), 7.51–7.46 (m, 3H), 7.00 (s, 1H); 13C{1H} NMR 2H), 6.92 (s, 1H); 13C{1H} NMR (101 MHz, CDCl3) δ 162.0,
(101 MHz, CDCl3) δ 161.2, 155.8, 140.3, 131.3, 131.1 (d, J = 3.0 152.5, 137.2, 136.0, 135.0, 130.4, 129.7, 129.1, 128.4, 126.4,
Hz), 130.8, 130.1 (d, J = 33.1 Hz), 129.0, 127.3 (d, J = 3.9 Hz), 126.0, 120.5, 102.1; IR (KBr): ν 3038, 3003, 1786, 1631, 1620,
126.8, 125.5, 123.5 (d, J = 271.1 Hz), 120.5, 100.9; IR (KBr): ν 1541, 1435, 1363, 1340, 1311, 1273, 1263, 1191, 1087, 996, 823,
3053, 3010, 1769, 1686, 1643, 1511, 1489, 1373, 1311, 1303, 741, 642, 637 cm−1. HRMS (ESI-TOF) m/z calcd for C15H20ClO2
1243, 1201, 1183, 1069, 934, 878, 724, 649 cm−1. HRMS (EI) [M + H]+: 257.0364, found 257.0384.
m/z calcd for C16H9F3O2 [M]+: 290.05546, found 290.05499.
6-Chloro-3-phenyl-1H-isochromen-1-one Purified acetate and petroleum ether (v/v = 1 : 20) as the eluent. Yield:
3-(p-Tolyl)-1H-isochromen-1-one (2k).7f Purified using ethyl
(2f).7f
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using ethyl acetate and petroleum ether (v/v = 1 : 20) as the 92% (109 mg). Light yellow oil. H NMR (CDCl3, 400 MHz): δ
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eluent. Yield: 72% (92 mg). Light yellow oil. H NMR (CDCl3, 8.28 (d, J = 8.0 Hz, 1H), 7.77–7.75 (m, 2H), 7.71–7.67 (m, 1H),
400 MHz,): δ 8.25 (d, J = 8.4 Hz, 1H), 7.90–7.87 (m, 2H), 7.48–7.44 (m, 2H), 7.26–7.24 (m, 2H), 6.89 (s, 1H), 2.39 (s, 3H);
7.51–7.44 (m, 5H), 6.89 (s, 1H); 13C{1H} NMR (101 MHz, 13C{1H} NMR (101 MHz, CDCl3) δ 162.4, 153.8, 140.3, 137.7,
CDCl3) δ 161.2, 154.0, 135.9, 135.3, 133.9, 131.6, 130.3, 129.2, 134.8, 129.6, 129.5, 129.2, 127.9, 125.8, 125.2, 120.4, 101.1,
128.9, 127.5, 125.3, 121.7, 101.0; IR (KBr): ν 3043, 3005, 1750, 17.1; IR (KBr): ν 3041, 3029, 2928, 1734, 1628, 1637, 1519,
1632, 1600, 1542, 1483, 1362, 1320, 1300, 1279, 1262, 1101, 1437, 1342, 1321, 1301, 1293, 1212, 1135, 1037, 989, 813, 724,
This journal is © The Royal Society of Chemistry 2021
Org. Biomol. Chem., 2021, 19, 6657–6664 | 6661