80
Tenglong Guo et al. / Chinese Journal of Catalysis 36 (2015) 78–85
= 8.02 (d, J = 7.3 Hz, 2H, aromatic CH), 7.77 (d, J = 15.7 Hz, 1H,
CH=CHCOPh), 7.66–7.56 (m, 3H, aromatic CH), 7.49 (m, 3H,
aromatic CH and CH=CHCOPh), 7.10 (t, 2H, aromatic CH).
(E)‐1‐Phenyl‐3‐(4‐(trifluoromethyl)phenyl)prop‐2‐en‐1
‐one (3i) [25]. Yield 80%, pale yellow solid. 1H NMR (400 MHz,
CDCl3): δ = 8.03 (d, J = 7.6 Hz, 2H, aromatic CH), 7.80 (d, J = 15.7
Hz, 1H, CH=CHCOPh), 7.73 (d, J = 8.1 Hz, 2H, aromatic CH), 7.66
(d, J = 8.1 Hz, 2H, aromatic CH), 7.60 (m, 2 H, aromatic CH and
CH=CHCOPh), 7.51 (t, J = 7.5 Hz, 2H, aromatic CH).
= 3.8 Hz, 6H, 2×CH3).
(E)‐1‐(2,4‐Dimethylphenyl)‐3‐phenylprop‐2‐en‐1‐one
(5d) [30]. Yield 84%, pale yellow solid. H NMR (400 MHz,
CDCl3): δ = 7.57 (m, 2H, aromatic CH), 7.52 (d, J = 16.0 Hz, 1H,
CH=CHCOPh), 7.47 (d, J = 7.6 Hz, 1H, aromatic CH), 7.40 (m, 3H,
aromatic CH), 7.19 (d, J = 16.0 Hz, 1H, CH=CHCOPh), 7.10 (d, J =
9.1 Hz, 2H, aromatic CH), 2.46 (s, 3H, CH3), 2.39 (s, 3H, CH3).
(E)‐1‐(2,5‐Dimethylphenyl)‐3‐phenylprop‐2‐en‐1‐one
1
1
(5e) [31]. Yield 82%, pale yellow solid. H NMR (400 MHz,
(E)‐Methyl 4‐(3‐oxo‐3‐phenylprop‐1‐en‐1‐yl)benzoate
(3j) [21]. Yield 79%, pale yellow solid. 1H NMR (400 MHz,
CDCl3): δ = 8.08–7.98 (m, 4 H, aromatic CH), 7.79 (d, J = 15.7,
1H, CH=CHCOPh), 7.67 (dd, J = 8.3, 1.8 Hz, 2H, aromatic CH),
7.62–7.55 (m, 2H, aromatic CH and CH=CHCOPh), 7.49 (m, 2H,
aromatic CH), 3.92 (s, 3H, CO2CH3).
(E)‐4‐(3‐Oxo‐3‐phenylprop‐1‐en‐1‐yl)benzonitrile (3k)
[27]. Yield 70%, pale yellow solid. 1H NMR (400 MHz, CDCl3): δ
= 8.01 (d, J = 7.4 Hz, 2H, aromatic CH), 7.78–7.70 (m, 3H, aro‐
matic CH and CH=CHCOPh), 7.68 (d, J = 8.6 Hz, 2H, aromatic
CH), 7.64–7.57 (m, 2H, aromatic CH and CH=CHCOPh), 7.51 (t,
2H, aromatic CH).
CDCl3): δ = 7.58 (m, 2H, aromatic CH), 7.48 (d, J = 16.1 Hz, 1H,
CH=CHCOPh), 7.40 (m, 3H, aromatic CH), 7.31 (s, 1H, aromatic
CH), 7.22–7.12 (m, 3H, aromatic CH and CH=CHCOPh), 2.41 (s,
3H, CH3), 2.38 (s, 3H, CH3).
(E)‐1‐(4‐Chlorophenyl)‐3‐phenylprop‐2‐en‐1‐one (5f)
[10]. Yield 86%, pale yellow solid. 1H NMR (400 MHz, CDCl3): δ
= 7.96 (d, J = 8.4 Hz, 2H, aromatic CH), 7.81 (d, J = 15.7 Hz, 1H,
CH=CHCOPh), 7.64 (m, 2H, aromatic CH), 7.47 (m, 3H, aromatic
CH and CH=CHCOPh), 7.41 (m, 3H, aromatic CH).
(E)‐1‐(4‐Fluorophenyl)‐3‐phenylprop‐2‐en‐1‐one (5g)
[10]. Yield 90%, pale yellow solid. 1H NMR (400 MHz, CDCl3): δ
= 8.06 (dd, J = 8.7, 5.5 Hz, 2H, aromatic CH), 7.82 (d, J = 15.7 Hz,
1H, CH=CHCOPh), 7.64 (m, 2H, aromatic CH), 7.51 (d, J = 15.7
Hz, 1H, CH=CHCOPh), 7.46–7.37 (m, 3H, aromatic CH), 7.17 (t, J
= X Hz, 2H, aromatic CH).
(E)‐3‐(4‐Nitrophenyl)‐1‐phenylprop‐2‐en‐1‐one
(3l)
1
[27]. Yield 58%, yellow solid. H NMR (400 MHz, CDCl3): δ =
8.28 (d, J = 8.7 Hz, 2H, aromatic CH), 8.04 (d, J = 7.3 Hz, 2H, ar‐
omatic CH), 7.81 (m, 3H, aromatic CH and CH=CHCOPh), 7.64
(m, 2H, aromatic CH and CH=CHCOPh), 7.53 (t, J = 7.6 Hz, 2H,
aromatic CH).
(E)‐3‐Phenyl‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one
(5h)
1
[25]. Yield 80%, yellow solid. H NMR (400 MHz, CDCl3): δ =
7.90–7.81 (m, 2H, thienyl CH and CH=CHCOPh), 7.70–7.60 (m,
3H, thienyl CH and aromatic CH), 7.40 (m, 4H, aromatic CH and
CH=CHCOPh), 7.18 (t, J = 4.2 Hz, 1H, thienyl CH).
(E)‐3‐(4‐Acetylphenyl)‐1‐phenylprop‐2‐en‐1‐one (3m)
1
[21]. Yield 51%, yellow solid. H NMR (400 MHz, CDCl3): δ =
8.01 (m, 4 H, aromatic CH), 7.80 (d, J = 15.8 Hz, 1H,
CH=CHCOPh), 7.71 (d, J = 8.4 Hz, 2H, aromatic CH), 7.64–7.56
(m, 2H, aromatic CH and CH=CHCOPh), 7.50 (m, 2H, aromatic
CH), 2.62 (s, 3H, CH3).
(E)‐1‐(Furan‐2‐yl)‐3‐phenylprop‐2‐en‐1‐one (5i) [25].
Yield 78%, yellow solid. 1H NMR (400 MHz, CDCl3): δ = 7.87 (d, J
= 15.8 Hz, 1H, CH=CHCOPh), 7.63 (m, 3H, furyl CH and aromatic
CH), 7.49–7.37 (m, 4H, aromatic CH and CH=CHCOPh), 7.32 (d, J
= 3.3 Hz, 1H, furyl CH), 6.57 (dd, J = 3.4 and 1.5 Hz, 1H, furyl
CH).
(E)‐1‐Phenyl‐3‐(thiophen‐2‐yl)prop‐2‐en‐1‐one
(3n)
1
[28]. Yield 75%, yellow solid. H NMR (400 MHz, CDCl3): δ =
8.00 (d, J = 7.6 Hz, 2H, aromatic CH), 7.94 (d, J = 15.3 Hz, 1H,
CH=CHCOPh), 7.57 (t, J = X Hz, 1H, aromatic CH), 7.49 (t, J = X
Hz, 2H, aromatic CH), 7.41 (d, J = 5.0 Hz, 1H, thienyl CH),
7.37–7.30 (m, 2H, thienyl CH and CH=CHCOPh), 7.11–7.03 (m, 1
H, thienyl CH).
(E)‐1‐(1‐Methyl‐1H‐indol‐3‐yl)‐3‐phenylprop‐2‐en‐1‐on
e (5j) [32]. Yield 85%, white solid. 1H NMR (400 MHz, CDCl3): δ
= 8.54 (dd, J = 6.5, 2.3 Hz, 1H, indolyl CH), 7.80 (d, J = 15.6 Hz,
1H, CH=CHCOPh), 7.75 (d, J = 2.6 Hz, 1H, indolyl CH), 7.61 (d, J =
7.3 Hz, 2H, aromatic CH), 7.38 (m, 3H, aromatic CH), 7.34–7.25
(m, 4H, aromatic CH and CH=CHCOPh), 3.77 (s, 3H, NCH3).
(E)‐3‐Phenyl‐1‐(p‐tolyl)prop‐2‐en‐1‐one (5a) [10]. Yield
83%, pale yellow solid. 1H NMR (400 MHz, CDCl3): δ = 7.95 (d, J
= 8.2 Hz, 2H aromatic CH), 7.82 (d, J = 15.7 Hz, 1H,
CH=CHCOPh), 7.64 (m, 2H, aromatic CH), 7.55 (d, J = 15.7 Hz,
1H, CH=CHCOPh), 7.41 (m, 3H, aromatic CH), 7.30 (d, J = 8.1 Hz,
2H, aromatic CH), 2.43 (s, 3H, CH3).
(E)‐1‐(4‐Methoxyphenyl)‐3‐phenylprop‐2‐en‐1‐one
(5b) [10]. Yield 89%, white solid. 1H NMR (400 MHz, CDCl3): δ
= 8.04 (d, J = 8.8 Hz, 2H, aromatic CH), 7.80 (d, J = 15.7 Hz, 1H,
CH=CHCOPh), 7.63 (m, 2H, aromatic CH), 7.55 (d, J = 15.6 Hz,
1H, CH=CHCOPh), 7.40 (m, 3H, aromatic CH), 6.97 (d, J = 8.8 Hz,
2H, aromatic CH), 3.86 (s, 3H, OCH3).
(E)‐1‐(3,4‐Dimethylphenyl)‐3‐phenylprop‐2‐en‐1‐one
(5c) [29]. Yield 83%, white solid. 1H NMR (400 MHz, CDCl3): δ =
7.80 (m, 3H, aromatic CH and CH=CHCOPh), 7.65 (m, 2H, aro‐
matic CH), 7.55 (d, J = 15.7 Hz, 1H, CH=CHCOPh), 7.46–7.39 (m,
3H, aromatic CH), 7.26 (d, J = 7.8 Hz, 1H, aromatic CH), 2.35 (d, J
1
m‐Tolyl cinnamate (5k) [33]. Yield 79%, white solid. H
NMR (400 MHz, CDCl3): δ = 7.89 (d, J = 16.0 Hz, 1H,
CH=CHCOOPh), 7.66–7.55 (m, 2H, aromatic CH), 7.44 (m, 3H,
aromatic CH), 7.31 (t, J = 7.7 Hz, 1H, aromatic CH), 7.09 (d, J =
7.6 Hz, 1H, aromatic CH), 7.01 (d, J = 8.6 Hz, 2H, aromatic CH),
6.66 (d, J = 16.0 Hz, 1H, CH=CHCOOPh), 2.40 (s, 3H, CH3).
4‐Chlorophenyl cinnamate (5l) [34]. Yield 77%, white
1
solid. H NMR (400 MHz, CDCl3): δ = 7.89 (d, J = 16.0 Hz, 1H,
CH=CHCOOPh), 7.60 (m, 2H, aromatic CH), 7.45 (m, 3H, aro‐
matic CH), 7.38 (d, J = 8.8 Hz, 2H, aromatic CH), 7.14 (d, J = 8.8
Hz, 2H, aromatic CH), 6.63 (d, J = 16.0 Hz, 1H, CH=CHCOOPh).
N‐Methyl‐N‐(p‐tolyl)cinnamamide (5m) [35]. Yield 90%,
white solid. 1H NMR (400 MHz, CDCl3): δ = 7.67 (d, J = 15.6 Hz,
1H, CH=CHCONAr), 7.29 (m, 5H), 7.22 (d, J = 8.0 Hz, 2H, aro‐
matic CH), 7.10 (d, J = 8.1 Hz, 2H, aromatic CH), 6.39 (d, J = 15.6
Hz, 1H, CH=CHCONAr), 3.38 (s, 3H, NCH3), 2.40 (s, 3H, CH3).