10.1002/adsc.201900752
Advanced Synthesis & Catalysis
3.79 (s, 3H ), 3.86 (s, 3H), 4.52 (dd, J = 8.0, 4.0, Hz, 1H),
6.58 (d, J = 2.0 Hz, 1H), 6.69 (dd, J = 8.0, 2.0 Hz, 1H), 6.80
(d, J = 8.4 Hz, 1H), 7.29 (dd, J = 8.0, 0.8 Hz, 1H), 7.37-7.46
(m, 1H), 7.56 (dd, J = 7.6, 1.2 Hz, 1H), 7.80 (d, J = 7.6 Hz,
1H); 13C NMR (100 MHz, CDCl3): 44.3, 47.1, 56.0, 56.1,
acetate in hexanes); 1H NMR (400 MHz, CDCl3): = 2.79
(dd, J = 19.2, 4.0 Hz, 1H), 3.27 (dd, J = 19.2, 8.0 Hz, 1H),
4.89 (dd, J = 8.0, 4.0 Hz, 1H ), 6.84-6.92 (m, 1H), 6.95 (dd,
J = 4.8, 3.6 Hz, 1H), 7.19 (dd, J = 4.8, 1.2 Hz, 1H) 7.39-7.51
(m, 2H), 7.56-7.66 (m, 1H), 7.80 (d, J = 7.6 Hz, 1H); 13C
110.7, 111.5, 119.9, 123.5, 126.9, 128.0, 135.2, 136.3, 136.8, NMR (100 MHz, CDCl3): 39.5, 47.3, 123.6, 124.4, 124.8,
148.2, 149.4, 158.2, 206.3; FTIR (neat): ν = 2994, 2938,
1712, 1596, 1264, 760 cm-1; HRMS (m/z): [M+Na]+ calcd
for C17H16O3Na: 291.0997; found: 291.0997.
126.8, 127.1, 128.4, 135.2, 136.2, 146.9, 156.9, and 205.0;
FTIR (neat): ν =3059, 2987, 1715, 1617, 1296 cm-1; HRMS
(m/z): [M+Na]+ calcd for C13H10OSNa: 237.0350; found:
237.0344.
3-(2,4-Dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one
(2v): 85% yield (56.9 mg); Yellow liquid; Rf 0.25 (20%
3-(Furan-2-yl)-2,3-dihydro-1H-inden-1-one (2ab): 83%
yield (41.1 mg); pale Yellow oil; Rf 0.43 (10% ethyl acetate
in hexanes); 1H NMR (400 MHz, CDCl3): = 2.87 (dd, J =
19.2, 3.2 Hz, 1H), 3.12 (dd, J = 18.8, 8.0 Hz, 1H), 4.65 (dd,
J = 7.6, 3.6 Hz, 1H), 6.07-6.40 (m 2H), 7.34 (s, 1H), 7.43 (t,
J = 7.6 Hz, 1H), 7.51 (d, J = 7.6 Hz, 1H), 7.61 (t, J = 7.6 Hz,
1H), 7.79 (d, J = 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3):
37.8, 42.9, 105.9, 110.3, 123.8, 126.7, 128.4, 135.1, 136.5,
142.2, 142.4, 154.8, 205.0; FTIR (neat): ν = 3054, 2982,
1712, 1601, 1212 cm-1; HRMS (m/z): [M+K]+ calcd for
C13H10O2K: 237.0318; found: 237.0298.
1
ethyl acetate in hexanes); H NMR (400 MHz, CDCl3):
2.65 (dd, J = 19.2, 3.6 Hz, 1H), 3.14 (dd, J = 19.2, 8.4 Hz,
1H), 3.72 (s, 3H ), 3.78 (s, 3H), 4.80 (dd, J = 8.0, 3.6 Hz,
1H), 6.39 (dd, J = 8.4, 2.4 Hz, 1H), 6.46 (d, J = 2.4 Hz, 1H),
6.85 (d, J = 8.4 Hz, 1H), 3.79 (d, J = 7.6 Hz, 1H), 7.38 (t, J
= 7.6 Hz, 1H), 3.78 (td, J = 15.2, 1.2 Hz, 1H), 7.78 (d, J =
7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3): 38.8, 45.5,
55.5, 55.5, 99.0, 104.2, 123.3, 124.2, 126.7, 127.5, 128.9,
134.8, 137.1, 158.3, 160.0 and 207.1; FTIR (neat): ν = 2998,
2934, 1710, 1610, 761 cm-1; HRMS (m/z): [M+Na]+ calcd
for C17H16O3Na: 291.0997; found: 291.0976.
3-(2,4,6-Trimethoxyphenyl)-2,3-dihydro-1H-inden-1-
one (2w): 82% yield (61.1 mg); Yellow liquid; Rf 0.32 (20%
ethyl acetate in hexanes); H NMR (400 MHz, CDCl3):
3-(1H-Indol-3-yl)-2,3-dihydro-1H-inden-1-one
(2ac):
84% yield (51.9 mg); Light yellow solid, mp 125 oC; Rf 0.38
(20% ethyl acetate in hexanes); 1H NMR (400 MHz,
CDCl3): = 2.79 (dd, J = 19.2, 4.0 Hz, 1H), 3.21 (dd, J =
18.8, 8.0 Hz, 1H), 4.82 (dd, J = 8.0, 4.0 Hz, 1H), 6.91 (d, J
= 2.4 Hz, 1H), 6.93-7.02 (m 1H),7.09-7.18 (m, 1H) 7.18-
7.23 (m, 2H), 7.28-7.35 (m, 1H), 7.35-7.42 (m, 2H), 7.50
(td, J = 15.2, 1.2 Hz, 1H), 7.78 (d, J = 7.6 Hz, 1H), 7.98 (s,
1H); 13C NMR (100 MHz, CDCl3): 36.1, 45.8, 111.5,
118.3, 119.0, 119.8, 121.7, 122.6, 123.6, 126.9, 127.9, 135.1,
136.8, 136.9, 157.9 and 206.6; FTIR (KBr): ν = 3462, 3051,
2986, 1705, 1262, 702 cm-1 .
1
2.66 (dd, J = 19.2, 3.6 Hz, 1H), 3.15 (dd, J = 19.2, 8.0 Hz,
1H), 3.70 (s, 6H), 3.87 (s, 3H), 4.81 (dd, J = 7.2, 2.4 Hz,
1H), 6.46-6.60 (m, 2H), 7.28 (t, J = 7.6 Hz, 1H), 7.38 (t, J =
7.6 Hz, 1H), 7.55 (t, J = 7.6 Hz, 1H), 7.78 (d, J = 7.6 Hz,
1H); 13C NMR (100 MHz, CDCl3): 38.8, 45.3, 56.3, 56.5,
56.8, 98.2, 112.8, 123.1, 123.4, 126.6, 127.6, 134.9, 137.1,
143.2, 148.8, 151.7, 158.2 and 206.9; FTIR (neat): ν = 2938,
2839, 1701, 1602, 1275, 1100 cm-1; HRMS (m/z): [M+H]+
calcd for C18H19O4: 299.1283; found: 299.1300.
3-(Anthracen-9-yl)-2,3-dihydro-1H-inden-1-one
(2x):
78% yield (60.0 mg); Yellow liquid; Rf 0.38 (10% ethyl
acetate in hexanes); H NMR (400 MHz, CDCl3): 3.21
6-Bromo-3-phenyl-2,3-dihydro-1H-inden-1-one (2ad):
86% yield (61.5 mg); Yellow solid, Rf 0.5 (10% ethyl
acetate in hexanes); 1H NMR (400 MHz, CDCl3): = 2.63
(dd, J = 19.6, 4.0 Hz, 1H), 3.17 (dd, J = 19.6, 8.0 Hz, 1H),
4.45 (dd, J = 8.0, 4.0 Hz, 1H), 7.00-7.13 (m, 3H), 7.13-7.30
(m, 3H), 7.58 (dd, J = 8.0, 2.0 Hz, 1H), 7.85 (d, J = 2.0 Hz,
1H); 13C NMR (100 MHz, CDCl3): 44.3, 47.1, 122.4,
126.5, 127.3, 127.7, 128.6, 129.2, 138.0, 138.6, 143.1, 156.6,
204.5; FTIR (KBr): ν = 3061, 3029, 1709, 1464, 1258 cm-1
HRMS (m/z): [M+Na]+ calcd for C15H11ONaBr: 308.9891;
found: 308.9912.
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(dd, J = 15.2, 4.4 Hz, 1H), 3.36 (dd, J = 15.2, 6.4 Hz, 1H),
6.05 (dd, J = 6.4, 4.4 Hz, 1H ), 6.91-6.98 (m, 1H), 7.00-7.08
(m, 1H), 7.16-7.22 (m, 2H), 7.25-7.31 (m, 1H), 7.37-7.41
(m, 2H), 7.45-7.50 (m, 1H), 7.51-7.58 (m, 1H), 7.90-7.98
(m, 1H), 7.94 (d, J = 6.8 Hz, 1H), 8.03 (dd, J = 6.8, 0.4 Hz,
1H) 8.38-8.45 (m, 2H); 13C NMR (100 MHz, CDCl3):
29.8, 38.9, 45.7, 123.3, 124.2, 124.9, 124.9, 125.1, 125.6,
125.9, 126.9, 127.4, 127.8, 128.2, 128.9, 129.8, 129.9, 131.6,
131.6, 132.4, 132.5, 135.6, 136.5, 160.3 and 205.9; HRMS
(m/z): [M+H]+ calcd for C23H17O: 309.1269; found:
309.1279.
3,6-Diphenyl-2,3-dihydro-1H-inden-1-one (2ae): 90%
o
yield (63.9 mg); Yellow solid, mp 110 C; Rf 0.43 (10%
ethyl acetate in hexanes); 1H NMR (400 MHz, CDCl3): =
2.66 (dd, J = 19.2, 3.2 Hz, 1H), 3.20 (dd, J = 19.2, 8.0 Hz,
1H), 4.51 (dd, J = 7.2, 3.2 Hz, 1H), 7.08 (d, J = 7.2 Hz, 2H),
7.14-7.34 (m, 5H), 7.37 (t, J = 7.6 Hz, 2H), 7.53 (d, J = 7.6
Hz, 2H), 7.72 (d, J = 8.0 Hz, 1H), 7.94 (s, 1H); 13C NMR
(100 MHz, CDCl3): 44.3, 47.3, 121.6, 127.1, 127.3, 127.8,
128.0, 129.1, 134.3, 137.5, 139.9, 141.3, 143.7, 157.0,
206.1; FTIR (KBr): ν = 3054, 2990, 1709, 1615, 1265, 699
cm-1 HRMS (m/z): [M+H]+ calcd for C21H17O: 285.1279;
found: 285.1244.
3-Styryl-2,3-dihydro-1H-inden-1-one (2y): 87% yield
(50.9 mg); Pale yellow liquid, Rf 0.46 (10% ethyl acetate in
hexanes) 1H NMR (400 MHz, CDCl3): 2.58 (dd, J = 19.2,
4.0 Hz, 1H), 3.07 (dd, J = 19.2, 8.0 Hz, 1H), 4.13-4.18 (m,
1H), 6.18 (dd, J = 15.6, 9.6 Hz, 1H), 6.64 (d, J = 15.6 Hz,
1H), 7.19-7.28 (m, 1H), 7.31 (t, J = 7.6 Hz, 2H), 7.35–7.44
(m, 3H), 7.51 (d, J = 8.0 Hz, 1H), 7.62 (t, J = 8.0 Hz, 1H),
7.79 (d, J = 7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3):
42.3, 44.0, 123.8, 126.4, 126.8, 127.8, 128.1, 128.8, 131.0,
131.6, 135.0, 136.6, 136.8, 156.8, 205.6; FTIR (neat): ν =
3026, 2965, 1708, 1604, 747 cm-1 HRMS (m/z): [M+H]+
calcd for C17H15O: 235.1123; found: 235.1144.
3-Phenyl-6-(phenylethynyl)-2,3-dihydro-1H-inden-1-
one (2af): 89% yield (65.8 mg); White solid, Rf 0.43 (10%
1
3-(Thiophen-2-yl)-2,3-dihydro-1H-inden-1-one (2aa):
84% yield (44.9 mg); Yellow liquid; Rf 0.53 (10% ethyl
ethyl acetate in hexanes); H NMR (400 MHz, CDCl3):
2.70 (dd, J = 19.2, 4.0 Hz, 1H), 3.25 (dd, J = 19.2, 8.0 Hz,
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