JOURNAL OF CHEMICAL RESEARCH 2014 699
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CH=CHCO), 7.42 (1H, d, J=7.2 Hz, 4′‑ArH), 7.32–7.24 (2H, m, 5′,6′‑
ArH), 7.04 (1H, d, J=1.6 Hz, 2‑ArH), 6.99 (1H, dd, J=8.4, 1.6 Hz,
6‑ArH), 6.76 (1H, d, J=8.4 Hz, 5‑ArH), 6.22 (1H, d, J=16 Hz,
CH=CHCO), 4.32 (2H, t, J=6.8 Hz, OCH2), 2.95 (2H, t, J=6.8 Hz,
CH2C6H4) ppm; 13C NMR (100 MHz, DMSO‑d6) δC 166.3, 148.3, 145.4,
145.2, 141.1, 131.6, 130.4, 129.2, 128.0, 125.4, 121.6, 121.4, 115.6, 114.7,
113.7, 63.9, 33.9 ppm; HRMS‑ESI C17H15BrO4 calcd [M–H]– 361.0075
(79Br), found 361.0083.
1169 cm–1; H NMR (400 MHz, DMSO‑d6) δH 9.60 (1H, br, 4‑OH),
9.13 (1H, br, 3‑OH), 8.17 (2H, d, J=12.8 Hz, 3′,5′‑ArH), 7.58 (2H, d,
J=12.8 Hz, 2′,6′‑ArH), 7.44 (1H, d, J=16 Hz, CH=CHCO), 7.04 (1H,
d, J=1.6 Hz, 2‑ArH), 6.98 (1H, d, J=8.0, 1.6 Hz, 6‑ArH), 6.76 (1H,
d, J=8.0 Hz, 5‑ArH), 6.21 (1H, d, J=16 Hz, CH=CHCO), 4.38 (2H,
t, J=6.4 Hz, OCH2), 3.10 (2H, t, J=6.4 Hz, CH2C6H4) ppm; 13C NMR
(100 MHz, DMSO‑d6) δC 166.3, 148.4, 146.6, 146.2, 145.5, 145.3,
130.2, 125.4, 123.3, 121.4, 115.7, 114.8, 113.6, 63.4, 34.2 ppm; HRMS‑
ESI C17H15NO6 calcd [M–H]– 328.0821, found 328.0814.
4-Cyanophenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate (19):
White solid; yield 1038 mg, 60.5%; m.p. 171–173 °C; IR (KBr) νmax
3465, 3339, 2222, 1696, 1634, 1597, 1533, 1357, 1300, 1275, 1178 cm–1;
1H NMR (400 MHz, DMSO‑d6) δH 7.77 (2H, d, J=8.0 Hz, 3′,5′‑ArH),
7.50 (2H, d, J=8.0 Hz, 2′,6′‑ArH), 7.43 (1H, d, J=16 Hz, CH=CHCO),
7.03 (1H, s, 2‑ArH), 6.98 (1H, d, J=8.0 Hz, 6‑ArH), 6.76 (1H, d,
J=8.0 Hz, 5‑ArH), 6.21 (1H, d, J=16 Hz, CH=CHCO), 4.35 (2H, t,
J=6.4 Hz, OCH2), 3.04 (2H, t, J=6.4 Hz, CH2C6H4) ppm; 13C NMR
(100 MHz, DMSO‑d6) δC 166.3, 148.3, 145.4, 145.3, 144.3, 132.1, 130.0,
125.4, 121.4, 118.9, 115.6, 114.7, 113.6, 109.2, 63.5, 34.4 ppm; HRMS‑
ESI C18H15NO4 calcd [M–H]– 308.0923, found 308.0929.
2-(4-Acetylphenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)acrylate (20):
White solid; yield 1019 mg, 56.2%; m.p. 183–185 °C; IR (KBr) νmax
3361, 3320, 1684, 1625, 1602, 1529, 1446, 1361, 1288, 1275, 1180 cm–1;
1H NMR (400 MHz, DMSO‑d6) δH 7.90 (2H, d, J=7.2 Hz, 3′,5′‑ArH),
7.44 (1H, d, J=16 Hz, CH=CHCO), 7.43 (2H, d, J=7.2 Hz, 2′,6′‑
ArH), 7.04 (1H, s, 2‑ArH), 6.98 (1H, d, J=8.0 Hz, 6‑ArH), 6.76 (1H,
d, J=8.0 Hz, 5‑ArH), 6.22 (1H, d, J=16 Hz, CH=CHCO), 4.36 (2H,
t, J=6.4 Hz, OCH2), 3.03 (2H, t, J=6.4 Hz, CH2C6H4), 2.55 (3H, s,
COCH3) ppm; 13C NMR (100 MHz, DMSO‑d6) δC 197.5, 166.4, 148.3,
145.4, 145.2, 143.9, 135.1, 129.1, 128.3, 125.4, 121.4, 115.5, 114.7, 113.7,
63.8, 26.6 ppm; HRMS‑ESI C19H18O5 calcd [M–H]– 325.1076, found
325.1072.
2-(2-Methylphenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)acrylate (13):
White solid; yield 804 mg, 48.5%; m.p. 129–131 °C; IR (KBr)
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νmax 3460, 3333, 1697, 1636, 1597, 1299, 1275, 1176 cm–1; H NMR
(400 MHz, DMSO‑d6) δH 7.46 (1H, d, J=16 Hz, CH=CHCO), 7.23–7.09
(4H, m, 3′,4′,5′,6′‑ArH), 7.04 (1H, d, J=1.6 Hz, 2‑ArH), 6.99 (1H, d,
J=8.0, 1.6 Hz, 6‑ArH), 6.77 (1H, d, J=8.0 Hz, 5‑ArH), 6.24 (1H, d,
J=16 Hz, CH=CHCO), 4.29 (2H, t, J=7.2 Hz, OCH2), 2.94 (2H, t,
J=7.2 Hz, CH2C6H4), 2.31 (3H, s, CH3) ppm; 13C NMR (100 MHz,
DMSO‑d6) δC 166.4, 148.3, 145.4, 145.2, 136.1, 136.0, 130.0, 129.4,
126.4, 125.9, 125.4, 121.4, 115.6, 114.7, 113.8, 63.4, 31.8, 18.9 ppm;
HRMS‑ESI C18H18O4 calcd [M–H]– 297.1127, found 297.1134.
2-(3-Methylphenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)acrylate (14):
White solid; yield 887 mg, 53.5%; m.p. 116–118 °C; IR (KBr) νmax
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3486, 3304, 1682, 1636, 1603, 1281, 1185 cm–1; H NMR (400 MHz,
DMSO‑d6) δH 9.59 (1H, s, br, 4‑OH), 9.14 (1H, s, br, 3‑OH), 7.45 (1H,
d, J=16 Hz, CH=CHCO), 7.19 (1H, t, J=7.2 Hz, 5′‑ArH), 7.11–7.01
(4H, m, 2′,4′,6′‑ArH & 2‑ArH), 6.99 (1H, d, J=8.0, 1.6 Hz, 6‑ArH), 6.76
(1H, d, J=8.0 Hz, 5‑ArH), 6.23 (1H, d, J=16 Hz, CH=CHCO), 4.30
(2H, t, J=6.8 Hz, OCH2), 2.90 (2H, t, J=6.8 Hz, CH2C6H4), 2.28 (3H,
s, CH3) ppm; 13C NMR (100 MHz, DMSO‑d6) δC 166.4, 148.4, 145.5,
145.1, 137.9, 137.3, 129.5, 128.5, 128.2, 126.9, 125.8, 125.4, 121.3,
115.7, 114.8, 113.8, 64.3, 34.4, 20.9 ppm; HRMS‑ESI C18H18O4 calcd
[M–H]– 297.1127, found 297.1125.
2-(4-Methylphenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)acrylate (15):
White solid; yield 784 mg, 47.3%; m.p. 158–160 °C (lit17: 161–162 °C);
IR (KBr) νmax 3458, 3237, 1686, 1637, 1605, 1517, 1263, 1187 cm–1;
1H NMR (400 MHz, DMSO‑d6) δH 7.45 (1H, d, J=16 Hz, CH=CHCO),
7.18–7.08 (4H, m, 2′,3′,5′,6′‑ArH), 7.05 (1H, d, J=1.6 Hz, 2‑ArH),
6.99 (1H, d, J=8.0, 1.6 Hz, 6‑ArH), 6.77 (1H, d, J=8.0 Hz, 5‑ArH),
6.23 (1H, d, J=16 Hz, CH=CHCO), 4.28 (2H, t, J=6.8 Hz, OCH2),
2.89 (2H, t, J=6.8 Hz, CH2C6H4), 2.26 (3H, s, CH3) ppm; 13C NMR
(100 MHz, DMSO‑d6) δC 166.4, 148.2, 145.4, 145.1, 135.2, 134.9, 128.9,
128.7, 125.4, 121.3, 115.6, 114.7, 113.8, 64.4, 34.0, 20.6 ppm; HRMS‑
ESI C18H18O4 calcd [M–H]– 297.1127, found 297.1137.
2-(3-Trifluoromethylphenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)
acrylate (16): White solid; yield 1011 mg, 51.7%; m.p. 120–122 °C; IR
(KBr) νmax 3458, 3116, 1667, 1607, 1443, 1328, 1281, 1241, 1116 cm–1;
1H NMR (400 MHz, DMSO‑d6) δH 7.66 (1H, s, 4′‑ArH), 7.63–7.51
(3H, m, 2′,5′,6′‑ArH), 7.47 (1H, d, J=16 Hz, CH=CHCO), 7.04 (1H, d,
J=1.6 Hz, 2‑ArH), 6.97 (1H, d, J=8.0, 1.6 Hz, 6‑ArH), 6.77 (1H, d,
J=8.0 Hz, 5‑ArH), 6.22 (1H, d, J=16 Hz, CH=CHCO), 4.36 (2H, t,
J=6.8 Hz, OCH2), 3.06 (2H, t, J=6.8 Hz, CH2C6H4) ppm; 13C NMR
(100 MHz, DMSO‑d6) δC 166.3, 148.3, 145.4, 145.2, 139.7, 133.1, 129.3,
129.2, 128.9, 125.4 (d), 125.4, 123.1 (d), 121.4, 115.6, 114.6, 113.6, 63.8,
34.0 ppm; HRMS‑ESI C18H15F3O4 calcd [M–H]– 351.0844, found
351.0851.
2-(4-Trifluoromethyl)phenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)
acrylate (17): White solid; yield 906 mg, 46.3%; m.p. 176–178 °C;
IR (KBr) νmax 3480, 3318, 1685, 1635, 1602, 1336, 1279, 1179 cm–1;
1H NMR (400 MHz, DMSO‑d6) δH 7.66 (2H, d, J=8.0 Hz, 3′,5′‑ArH),
7.52 (2H, d, J=8.0 Hz, 2′6′‑ArH), 7.45 (1H, d, J=16 Hz, CH=CHCO),
7.04 (1H, d, J=2.0 Hz, 2‑ArH), 6.98 (1H, d, J=8.0, 2.0 Hz, 6‑ArH),
6.76 (1H, d, J=8.0 Hz, 5‑ArH), 6.22 (1H, d, J=16 Hz, CH=CHCO),
4.36 (2H, t, J=6.8 Hz, OCH2), 3.05 (2H, t, J=6.8 Hz, CH2C6H4) ppm;
13C NMR (100 MHz, DMSO‑d6) δC 166.4, 148.3, 145.4, 145.3, 143.2,
129.7, 127.3, 126.9, 125.1 (q), 121.4, 115.6, 114.7, 113.6, 63.7, 34.2 ppm;
HRMS‑ESI C18H15F3O4 calcd [M–H]– 351.0844, found 351.0856.
2-(4-Nitrophenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate (18):
Yellow solid (970 mg, 53.0%; m.p. 174–176 °C (lit.17 168–169 °C); IR
(KBr) νmax 3474, 3420, 1691, 1633, 1597, 1508, 1355, 1340, 1299, 1277,
2-(3,5-Difluorophenyl)ethy (E)-3-(3,4-dihydroxyphenyl)acrylate (21):
White solid; yield 918 mg, 51.6%; m.p. 148–150 °C; IR (KBr)
νmax 3484, 3301, 1683, 1636, 1603, 1535, 1391, 1363, 1303, 1281,
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1186 cm–1; H NMR (400 MHz, DMSO‑d6) δH 7.45 (1H, d, J=16 Hz,
CH=CHCO), 7.09–7.03 (3H, m, 2′,4′,6′‑ArH), 7.03 (1H, s, 2‑ArH), 6.98
(1H, d, J=8.4 Hz, 6‑ArH), 6.77 (1H, d, J=8.4 Hz, 5‑ArH), 6.23 (1H,
d, J=16 Hz, CH=CHCO), 4.34 (2H, t, J=6.4 Hz, OCH2), 2.98 (2H, t,
J=6.4 Hz, CH2C6H3) ppm; 13C NMR (100 MHz, DMSO‑d6) δC 166.3,
162.2 (dd), 148.3, 145.4, 145.3, 142.9 (t), 125.4, 121.4, 115.6, 114.7,
113.6, 112.0 (dd), 101.8 (t), 63.5, 34.0 ppm; HRMS‑ESI C17H14F2O4
calcd [M–H]– 319.0782, found 319.0778.
2-(4-Hydroxy-3-nitrophenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)
acrylate (22): Yellow solid; yield 1103 mg, 57.5%; m.p. 172–174 °C;
IR (KBr) νmax 3478, 3310, 1686, 1634, 1604, 1536,1282, 1189 cm–1;
1H NMR (400 MHz, DMSO‑d6) δH 7.82 (1H, s, 2′‑ArH), 7.47 (1H, d,
J=8.4 Hz, 6′‑ArH), 7.44 (1H, d, J=16 Hz, CH=CHCO), 7.07 (1H,
d, J=8.4 Hz, 5′‑ArH), 7.04 (1H, s, 2‑ArH), 6.98 (1H, d, J=8.0 Hz,
6‑ArH), 6.76 (1H, d, J=8.0 Hz, 5‑ArH), 6.22 (1H, d, J=16 Hz,
CH=CHCO), 4.29 (2H, t, J=6.4 Hz, OCH2), 2.93 (2H, t, J=6.4 Hz,
CH2C6H3) ppm; 13C NMR (100 MHz, DMSO‑d6) δC 166.3, 150.6,
148.3, 145.4, 145.2, 136.3, 136.0, 129.4, 125.4, 124.9, 121.4, 119.0,
115.6, 114.7, 113.7, 63.9, 32.9 ppm; HRMS‑ESI C17H15NO7 calcd
[M–H]– 344.0770, found 344.0764.
2-(2,4,5-Trifluorophenyl)ethyl (E)-3-(3,4-dihydroxyphenyl)acrylate
(23): White solid; yield 1010 mg, 53.9%; m.p. 146–148 °C; IR (KBr)
νmax 3489, 3315, 1688, 1633, 1601, 1522, 1279, 1180 cm–1. H NMR
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(400 MHz, DMSO‑d6): δH 7.57–7.40 (3H, m, 3′,6′‑ArH & CH=CHCO),
7.04 (1H, s, 2‑ArH), 6.98 (1H, d, J=8.0 Hz, 6‑ArH), 6.76 (1H, d,
J=8.0 Hz, 5‑ArH), 6.21 (1H, d, J=16 Hz, CH=CHCO), 4.31 (2H, t,
J=6.4 Hz, OCH2), 2.95 (2H, t, J=6.4 Hz, CH2C6H2) ppm. 13C NMR
(100 MHz, DMSO‑d6): δC 166.2, 148.3, 145.4, 145.3, 125.3, 122.0
(m), 121.4, 118.9 (dd), 115.6, 114.7, 113.5, 105.6 (dd), 62.6, 37.2 ppm.
HRMS‑ESI C17H13F3O4 calcd [M–H]– 337.0688, found 337.0685.
3-Phenylpropyl (E)-3-(3,4-dihydroxyphenyl)acrylate (24): White
solid; yield 787 mg, 47.5%; m.p. 122–124 °C (lit20: 123–124 °C);
IR (KBr) νmax 3495, 3338, 1683, 1638, 1602, 1278, 1184 cm–1;
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