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O rP gl ea na si ce &d Bo i on mo to al e dc juu l sa tr mC ha er mg i ins ts ry
Journal Name
ARTICLE
14.4, 7.2, 1.6 Hz, 2H), 6.75 (s, 1H); 13C NMR (100 MHz, CDCl
2
53.1224.
1
-Phenyl-3-(m-tolyl)propane-1,3-dione (2e):6b light brown oil (1e (ppm): 187.0, 184.7, 136.4, 135.1, 132.8, 13D1O.9I,: 1103.110.83,91/C380O.9B,01138061.2H,
1
as substrate for 86% yield; 1e’ as substrate for 85% yield); H NMR 128.9, 127.4, 127.1, 98.5.
(400 MHz, CDCl
3
) δ (ppm): 16.87 (s, 1H), 8.01–7.99 (m, 2H), 7.81– 1-(4-Fluorophenyl)-3-phenylpropane-1,3-dione (2m):6b white
7
.78 (m, 2H), 7.58-7.54 (m, 1H), 7.49 (t, J = 7.2 Hz, 2H), 7.40–7.37 solid (1m as substrate for 86% yield; 1m’ as substrate for 85%); mp
m, 2H), 6.85 (s, 1H), 2.45 (s, 3H); 13C NMR (100 MHz, CDCl
1
(
(
3 3
) δ 78.0−79.2 °C . H NMR (400 MHz, CDCl ) δ (ppm): 16.85 (s, 1H),
ppm): 186.2, 185.8, 138.6, 135.7, 135.7, 133.4, 132.5, 128.8, 128.7, 8.03–7.97 (m, 4H), 7.58–7.54 (m, 1H), 7.51–7.47 (m, 2H), 7.17 (t, J
1
27.9, 127.3, 124.5, 93.3, 21.6.
-(4-(Tert-butyl)phenyl)-3-phenylpropane-1,3-dione (2f):8e white 185.2, 165.5, (d, JC-F = 252.4 Hz), 135.4, 132.6, 132.0 (d, JC-F = 3.0
= 8.4 Hz, 2H), 6.80 (s, 1H); 13C NMR (100 MHz, CDCl
) δ (ppm):
3
1
solid (1f as substrate for 85% yield; 1f’ as substrate for 70% yield); Hz),, 129.7 (d, JC-F = 9.1 Hz), 128.8, 127.2, 115.9 (d, JC-F = 21.8 Hz),
1
) δ (ppm): 16.91 (s, 92.9; 19F NMR (376 MHz, CDCl
mp 94.6−96.4 °C. H NMR (400 MHz, CDCl
3
3
) δ (ppm): -106.3 (dd, JC-F = 4.8, 1.9
1
6
1
9
1
H), 8.00–7.98 (m, 2H), 7.94 (d, J = 8.4 Hz, 2H), 7.57-7.47 (m, 5H), Hz).
.85 (s, 1H), 1.37 (s, 9H); 13C NMR (100 MHz, CDCl
) δ (ppm):
3
1
-Phenyl-3-(4-(trifluoromethyl)phenyl)propane-1,3-dione
2n):6,8c white solid (80% yield); mp 96.3−97.2 °C. 1H NMR (400
86.0, 185.5, 156.4, 135.8, 132.9, 132.4, 128.8, 127.3, 127.2, 125.8,
3.1, 35.2, 31.3.
-Phenyl-3-(o-tolyl)propane-1,3-dione (2g):20b slight yellow oil
(
MHz, CDCl ) δ (ppm): 16.72 (s, 1H), 8.09 (d, J = 8.4 Hz, 2H), 8.00
3
(d, J = 7.6 Hz, 2H), 7.75 (d, J = 8.4 Hz, 2H), 7.59 (t, J = 7.2 Hz, 1H),
1
(78% yield); H NMR (400 MHz, CDCl
3
) δ (ppm): 16.56 (s, 1H),
.51 (t, J = 7.6 Hz, 2H), 6.87 (s, 1H); 13C NMR (100 MHz, CDCl
3
) δ
7
7
7
2
1
9
1
.85 (d, J = 7.6 Hz, 2H), 7.45 (dd, J = 15.6, 7.6 Hz, 2H), 7.37 (t, J =
.6 Hz, 2H), 7.27 (t, J = 7.6 Hz, 1H), 7.19-7.15 (m, 2H), 6.44 (s, 1H),
(
ppm): 187.2, 183.5, 138.9, 135.4, 133.9 (d, JC-F = 32.5 Hz),133.0,
28.9, 127.6, 127.5, 125.8 (q, JC-F = 3.7 Hz), 123.8 (d, JC-F = 270.9
Hz), 93.8; 19F NMR (376 MHz, CDCl
) δ (ppm): -63.0.
-(4-Bromophenyl)-3-phenylpropane-1,3-dione (2o): light yellow
1
.46 (s, 3H); 13C NMR (100 MHz, CDCl
) δ (ppm): 190.6, 185.1,
3
3
37.2, 136.8, 135.4, 132.6, 131.6, 130.9, 128.8, 128.4, 127.3, 125.9,
7.4, 20.8.
-(3-Methoxyphenyl)-3-phenylpropane-1,3-dione (2h):6 white
6
1
1
solid (61% yield); mp 91.4−93.2 °C . H NMR (400 MHz, CDCl
3
) δ
(ppm): 16.80 (s, 1H), 7.98 (d, J = 7.6 Hz, 2H), 7.85 (d, J = 8.4 Hz,
1
solid (74% yield); mp 57.9−58.5 °C. H NMR (400 MHz, CDCl
3
) δ
2
7
1
9
1
H), 7.62 (d, J = 8.4 Hz, 2H), 7.56 (t, J = 7.2 Hz, 1H), 7.49 (t, J =
.6 Hz, 2H), 6.81 (s, 1H); 13C NMR (100 MHz, CDCl
) δ (ppm):
(
ppm): 16.86 (s, 1H), 8.04–7.94 (m, 2H), 7.61– 7.52 (m, 3H), 7.48
dd, J = 10.4, 4.8 Hz, 2H), 7.39 (t, J = 8.0 Hz, 1H), 7.09 (dd, J = 8.4,
.4 Hz, 1H), 6.84 (s, 1H), 3.88 (s, 3H); 13C NMR (100 MHz, CDCl
δ (ppm): 186.0, 185.5, 160.0, 137.2, 135.5, 132.6, 129.8, 128.8,
3
(
86.1, 184.7, 135.5, 134.6, 132.8, 132.1, 128.9, 128.8, 127.4, 127.3,
2
3
)
3.1.
(2p):6a
-(3-Bromophenyl)-3-phenylpropane-1,3-dione
light
1
27.3, 119.7, 118.7, 112.2, 93.4, 55.6.
-(2-Methoxyphenyl)-3-phenylpropane-1,3-dione (2i):6 white
1
yellow solid (56% yield); mp 66.7−67.9 °C . H NMR (400 MHz,
1
CDCl
3
) δ (ppm): 16.73 (s, 1H), 8.11 (s, 1H), 7.99 (d, J = 7.6 Hz, 2H),
.91 (d, J = 7.6 Hz, 1H), 7.67 (dd, J = 8.0, 0.8 Hz, 1H), 7.57 (t, J =
.8 Hz, 1H), 7.50 (t, J = 7.6 Hz, 2H), 7.37 (t, J = 8.0 Hz, 1H), 6.81 (s,
H); 13C NMR (100 MHz, CDCl
) δ (ppm): 186.2, 184.2, 137.7,
35.3, 135.3, 132.9, 130.4, 130.3, 128.9, 127.4, 125.8, 123.1, 93.4.
1
solid (86% yield); enol/ ketone = 91:9; mp 62.2−64.0 °C . H NMR
7
6
1
1
1
(
400 MHz, CDCl
.44 (m, 4H), 7.16 (s, 1H), 7.07 (t, J = 7.6 Hz, 1H), 7.00 (d, J = 8.4
Hz, 1H), 3.95 (s, 3H); 13C NMR (100 MHz, CDCl
) δ (ppm): 185.9,
84.3, 158.6, 136.1, 133.2, 132.3, 130.4, 128.7, 127.3, 125.0, 120.9,
3
) δ (ppm): 16.88 (s, 1H), 7.98-7.94 (m, 3H), 7.56–
7
3
3
1
1
1
(2q):6a
-(2-Bromophenyl)-3-phenylpropane-1,3-dione
light
11.8, 98.6, 55.9.
1
brown oil (80% yield); H NMR (400 MHz, CDCl
3
) δ (ppm): 16.24
-(4-Chlorophenyl)-3-phenylpropane-1,3-dione (2j):6a white solid
(
s, 1H), 7.96 (d, J = 7.2 Hz, 2H), 7.68 (d, J = 8.0 Hz, 1H), 7.61 (dd, J
(
1j as substrate for 89% yield; 1j’ as substrate for 88% yield); mp
=
7.6, 1.6 Hz, 1H), 7.56 (t, J = 7.2 Hz, 1H), 7.48 (t, J = 7.6 Hz, 2H),
4.6−86.1 °C (lit.20a mp 82.5-84 °C). H NMR (400 MHz, CDCl
1
) δ
8
3
7
.41 (t, J = 7.2 Hz, 1H), 7.32 (td, J = 7.6, 1.6 Hz, 1H), 6.67 (s, 1H);
(
ppm): 16.80 (s, 1H), 7.98 (d, J = 7.2 Hz, 2H), 7.93 (t, J = 6.8 Hz,
H), 7.56 (t, J = 7.2 Hz, 1H), 7.53–7.39 (m, 4H), 6.81 (s, 1H); 13C
NMR (100 MHz, CDCl ) δ (ppm): 185.9, 184.6, 138.8, 135.4, 134.1,
32.7, 129.1, 128.8, 128.6, 127.3, 93.1.
13C NMR (100 MHz, CDCl
3
) δ (ppm): 188.7, 184.1, 138.6, 134.9,
2
1
34.0, 132.8, 131.8, 130.1, 128.8, 127.6, 127.4, 120.3, 98.3.
-(3-Oxo-3-phenylpropanoyl)benzonitrile (2r):6a white solid (96%
3
4
1
1
yield); mp 154.0−155.6 °C . H NMR (400 MHz, CDCl
3
) δ (ppm):
1
-(3-Chlorophenyl)-3-phenylpropane-1,3-dione (2k):3b brick-red
1
6.67 (s, 1H), 8.07 (d, J = 8.4 Hz, 2H), 8.00 (d, J = 7.2 Hz, 2H), 7.78
1
solid (89% yield); mp 65.2−66.6 °C . H NMR (400 MHz, CDCl
3
) δ
(d, J = 8.4 Hz, 2H), 7.59 (t, J = 7.2 Hz, 1H), 7.51 (t, J = 7.6 Hz, 2H),
(
ppm): δ 16.73 (s, 1H), 8.00–7.95 (m, 3H), 7.86 (d, J = 7.6 Hz, 1H),
.86 (s, 1H); 13C NMR (100 MHz, CDCl
6
1
1
3
) δ (ppm): 187.7, 182.4,
7
6
1
1
.57 (t, J = 7.2 Hz, 1H), 7.53–7.48 (m, 3H), 7.43 (t, J = 8.0 Hz, 1H),
.81 (s, 1H); 13C NMR (100 MHz, CDCl
) δ (ppm): 186.2, 184.2,
39.5, 135.3, 133.2, 132.6, 129.0, 127.7, 127.5, 118.2, 115.6, 94.1.
3
(2s):6a
-(Naphthalen-1-yl)-3-phenylpropane-1,3-dione
white
) δ
37.5, 135.3, 135.1, 132.8, 132.4, 130.1, 128.9, 127.4, 125.4, 93.4.
-(2-Chlorophenyl)-3-phenylpropane-1,3-dione (2l):3b brown
1
solid (90% yield); mp 49.3−50.8 °C . H NMR (400 MHz, CDCl
3
(
ppm): 16.82 (s, 1H), 8.55 (d, J = 8.4 Hz, 1H), 8.00–7.98 (m, 3H),
1
solid (90% yield); mp 50.2−51.6 °C . H NMR (400 MHz, CDCl
3
) δ
7
6
1
.93–7.91 (m, 1H), 7.83 (dd, J = 7.2, 0.8 Hz, 1H), 7.62–7.47 (m, 6H),
.73 (s, 1H); 13C NMR (100 MHz, CDCl
) δ (ppm): 190.7, 184.6,
(ppm): 16.34 (s, 1H), 7.97–7.95 (m, 2H), 7.68 (dd, J = 7.2, 2.0 Hz,
3
1
H), 7.56 (dd, J = 8.4, 6.4 Hz, 1H), 7.50–7.47 (m, 3H), 7.39 (dtd, J =
35.2, 135.1, 134.0, 132.7, 131.9, 130.3, 128.8, 128.7, 127.5, 127.3,
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