Molecules 2021, 26, 2637
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1
28.6, 128.7 (2C), 129.7, 129.9, 132.7, 134.6, 135.8, 142.5, 151.2, 155.1, 197.8 ppm; HRMS (ESI)
+
+
calcd. for C H O [M + H] 341.1536, found 341.1538.
24
21
2
3
-(5-Methylfuran-2-yl)-3-phenyl-1-(thiophen-2-yl)propan-1-one (1g). Yield 110 mg (74%), pale
1
2
3
yellow oil; H NMR (400 MHz, CDCl )
Hz, 1H, CH ), 3.69 (dd, J = 16.2 Hz, J = 7.3 Hz, 1H, CH ), 4.75 (t, J = 7.3 Hz, 1H, CH), 5.83
δ
= 2.21 (s, 3H, CH ), 3.44 (dd, J = 16.2 Hz, J = 7.3
3
3
2
3
3
2
2
3
3
(
d, J = 3.1 Hz, 1H, H ), 5.91 (d, J = 3.1 Hz, 1H, HFur), 7.08–7.10 (m, 1H, HTh), 7.18–7.22
Fur
(
m, 1H, HAr), 7.29–7.32 (m, 4H, HAr), 7.59–7.60 (m, 1H, HTh), 7.70–7.71 (m, 1H, HTh) ppm;
1
3
C NMR (100 MHz, CDCl3)
δ
= 12.9, 40.2, 44.0, 105.4, 106.1, 126.2, 127.3 (2C), 127.4, 128.0
+
(
[
2C), 131.2, 133.0, 141.4, 143.8, 150.6, 154.0, 189.9 ppm; HRMS (ESI) calcd. for C H SO
18 17 2
+
M + H] 297.0944, found 297.0940.
3
-(5-Methylfuran-2-yl)-1-phenyl-3-(4-methylphenyl)propan-1-one (1h) [32]. Yield 111 mg (73%),
1
pale yellow oil; H NMR (400 MHz, CDCl )
δ = 2.22 (s, 3H CH ), 2.32 (s, 3H, CH ), 3.52
3
3 3
2
3
2
3
(dd, J = 16.9 Hz, J = 7.2 Hz, 1H, CH ), 3.78 (dd, J = 16.9 Hz, J = 7.2 Hz, 1H, CH ), 4.76
2
2
3
3
3
(t, J = 7.2 Hz, 1H, CH), 5.85 (d, J = 2.8 Hz, 1H, H ), 5.90 (d, J = 2.8 Hz, 1H, HFur), 7.12
Fur
3
3
(AA’BB’-system, J = 7.8 Hz, 2H, H ), 7.22 (AA’BB’-system, J = 7.8 Hz, 2H, HAr), 7.43–7.46
Ar
13
(m, 2H, H ), 7.53–7.57 (m, 1H, H ), 7.94–7.96 (m, 2H, H ) ppm; C NMR (100 MHz,
Ar Ar Ar
CDCl3) δ = 13.7, 21.1, 40.3, 44.0, 106.1, 106.5, 127.9 (2C), 128.2 (2C), 128.7 (2C), 129.3 (2C),
133.1, 136.3, 137.3, 139.4, 151.1, 155.3, 197.9 ppm.
3
-(4-Methoxyphenyl)-3-(5-methylfuran-2-yl)-1-phenylpropan-1-one (1i) [32]. Yield 120 mg (75%),
1
2
pale yellow oil; H NMR (400 MHz, CDCl )
δ
= 2.22 (s, 3H, CH ), 3.51 (dd, J = 16.8 Hz,
3
3
3
3
J = 7.5 Hz, 1H, CH ), 3.72–3.77 (m, 1H, CH ), 3.77 (s, 3H, OCH ), 4.73 (t, J = 7.5 Hz, 1H,
2
2
3
3
3
CH), 5.83 (d, J = 2.8 Hz, 1H, H ), 5.87 (d, J = 2.8 Hz, 1H, HFur), 6.84 (AA’BB’-system,
Fur
3
3
J = 8.6 Hz, 2H, H ), 7.24 (AA’BB’-system, J = 8.6 Hz, 2H, H ), 7.42–7.46 (m, 2H, H ),
Ar
Ar
Ar
= 13.7,
7
.53–7.57 (m, 1H, HAr), 7.93–7.95 (m, 2H, HAr) ppm; 13C NMR (100 MHz, CDCl3)
δ
3
1
9.8, 44.0, 55.3, 106.1, 106.4, 114.1 (2C), 128.2 (2C), 128.7 (2C), 129.0 (2C), 133.1, 134.4, 137.2,
51.1, 155.4, 158.5, 198.0 ppm.
3
-(4-Bromophenyl)-3-(5-methylfuran-2-yl)-1-phenylpropan-1-one (1j) [32]. Yield 157 mg (85%),
1
2
3
orange oil; H NMR (400 MHz, CDCl )
Hz, 1H, CH ), 3.78 (dd, J = 17.2 Hz, J = 7.7 Hz, 1H, CH ), 4.78 (t, J = 7.7 Hz, 1H, CH),
δ
= 2.24 (s, 3H, CH ), 3.55 (dd, J = 17.2 Hz, J = 7.7
3
3
2
3
3
2
2
3
3
3
5
.87 (d, J = 2.6 Hz, 1H, H ), 5.93 (d, J = 2.6 Hz, 1H, H ), 7.23 (AA’BB’-system, J = 8.1
Fur Fur
3
3
Hz, 2H, H ), 7.43 (AA’BB’-system, J = 8.1 Hz, 2H, H ), 7.45 (d, J = 7.5 Hz, 2H, HAr), 7.56
Ar
Ar
3
3
13
(t, J = 7.5 Hz, 1H, H ), 7.96 (d, J = 7.5 Hz, 2H, H ) ppm; C NMR (100 MHz, CDCl3)
Ar Ar
δ
= 13.6, 39.9, 43.5, 106.1, 106.7, 120.6, 128.1 (2C), 128.7 (2C), 129.8 (2C), 131.6 (2C), 133.2,
136.9, 141.3, 151.3, 154.4, 197.3 ppm.
3
-(5-Methylfuran-2-yl)-3-(4-nitrophenyl)-1-phenylpropan-1-one (1k). Yield 134 mg (80%), pale
1
2
3
yellow oil; H NMR (400 MHz, CDCl )
Hz, 1H, CH ), 3.80 (dd, J = 17.3 Hz, J = 7.3 Hz, 1H, CH ), 4.88 (t, J = 7.3 Hz, 1H, CH),
5
δ
= 2.23 (s, 3H, CH ), 3.61 (dd, J = 17.3 Hz, J = 7.3
3
3
2
3
3
2
2
3
3
.87 (d, J = 3.1 Hz, 1H, H ), 5.96 (d, J = 3.1 Hz, 1H, H ), 7.43–7.47 (m, 2H, H ), 7.49
Fur Fur Ar
3
(
(
AA’BB’-system, J = 8.7 Hz, 2H, H ), 7.55–7.58 (m, 1H, HAr), 7.93–7.94 (m, 2H, HAr), 8.14
AA’BB’-system, J = 8.7 Hz, 2H, HAr) ppm; C NMR (100 MHz, CDCl3)
Ar
3
13
δ
= 12.9, 39.6, 42.6,
1
05.6, 106.6, 123.2 (2C), 127.5 (2C), 128.1 (2C), 128.3 (2C), 132.8, 136.1, 146.3, 149.2, 151.2,
+
+
1
52.6, 196.2 ppm; HRMS (ESI) calcd. for C H NO [M + H] 336.1230, found 336.1224.
20
18
4
3
-(5-Methylfuran-2-yl)-1-phenyl-3-(thiophen-2-yl)propan-1-one (1l). Yield 101 mg (68%), pale
1
2
3
yellow oil; H NMR (400 MHz, CDCl )
Hz, 1H, CH ), 3.77 (dd, J = 16.9 Hz, J = 7.3 Hz, 1H, CH ), 5.09 (t, J = 7.3 Hz, 1H, CH),
δ
= 2.23 (s, 3H, CH ), 3.62 (dd, J = 16.9 Hz, J = 7.3
3
3
2
3
3
2
2
3
3
5
.85 (d, J = 3.0 Hz 1H, H ), 5.98 (d, J = 3.0 Hz, 1H, H ), 6.89–6.91 (m, 2H, HAr), 7.14 (d,
Fur
Fur
3
3
J = 4.6 Hz, 1H, H ), 7.43–7.47 (m, 2H, H
), 7.55 (t, J = 4.6 Hz, 1H, H ), 7.94–7.96 (m,
Th
Ar+Th
Th
13
2
H, H ) ppm; C NMR (100 MHz, CDCl3)
δ
= 13.7, 35.9, 44.8, 106.2, 106.7, 124.0, 124.9,
Ar
1
26.8, 128.3 (2C), 128.7 (2C), 133.3, 137.2, 145.9, 151.3, 154.3, 197.4 ppm; HRMS (ESI) calcd.
+
+
for C H SO [M + H] 297.0944, found 297.0942.
18
17
2