10.1002/adsc.201701469
Advanced Synthesis & Catalysis
(m, 2H), 7.58–7.42 (m, 6H). 13C NMR (100 MHz, CDCl3)
δ 177.6, 146.9, 139.7, 135.8, 133.2, 130.9, 130.3, 130.1,
129.1, 128.8, 127.4, 127.3, 120.2, 93.2, 87.1. HRMS (EI)
Calcd for C21H15O [M+H]+, 283.1117; found, 283.1124.
8.06 (d, J = 7.6 Hz, 1H), 7.63 (d, J = 7.6 Hz, 2H), 7.49 –
7.42 (m, 3H), 7.39 (t, J = 6.8 Hz, 3H). 13C NMR (100 MHz,
CDCl3) δ 176.7, 135.8, 133.5, 133.3, 133.0, 132.5, 131.5,
130.9, 128.6, 126.7, 119.9, 93.9, 88.2. HRMS (EI) Calcd
for C15H10ClO [M+H]+, 241.0415; found, 241.0411.
1-(4-Fluorophenyl)-3-phenylprop-2-yn-1-one
(2d):
1
White solid. mp 62−63 °C. H NMR (400 MHz, CDCl3) δ
8.44 – 7.94 (m, 2H), 7.57 (d, J = 7.2 Hz, 2H), 7.43 – 7.35
(m, 1H), 7.32 (t, J = 7.2 Hz, 2H), 7.08 (t, J = 8.4 Hz, 2H).
13C NMR (100 MHz, CDCl3) δ 175.2, 166.6, 164.1, 132.3,
132.0, 131.1 (d, J = 9.6 Hz), 129.9, 127.7, 118.8, 114.8 (d,
J = 22.4 Hz), 92.3, 85.5. HRMS (EI) Calcd for
C15H10FO [M+H]+, 225.0710; found, 225.0702.
1-(2-Methoxyphenyl)-3-phenylprop-2-yn-1-one (2m):
White solid. mp 79−81 °C.1H NMR (400 MHz, CDCl3) δ
8.08 (dd, J = 7.6, 2.0 Hz, 1H), 7.63 (dt, J = 7.2, 1.6 Hz,
2H), 7.52 (t, J = 8.0 Hz, 1H), 7.46 – 7.34 (m, 3H), 7.10 –
6.96 (m, 2H), 3.94 (s, 3H). 13C NMR (100 MHz, CDCl3) δ
176.7, 159.7, 134.9, 132.9, 132.6, 130.4, 128.5, 126.6,
120.6, 120.2, 112.1, 91.5, 89.1, 55.9. HRMS (EI) Calcd for
C16H13O2 [M+H]+, 237.0910; found, 237.0904.
1-(4-Chlorophenyl)-3-phenylprop-2-yn-1-one
(2e):
White solid. mp 103−105 °C.1H NMR (400 MHz, CDCl3)
1-(2,4-Difluorophenyl)-3-phenylprop-2-yn-1-one (2n):
δ 8.17 (d, J = 8.4 Hz, 2H), 7.68 (d, J = 7.6 Hz, 2H), 7.50 (d, White solid. mp 110−112 °C. 1H NMR (400 MHz, CDCl3)
J = 8.0 Hz, 3H), 7.43 (t, J = 7.6 Hz, 2H). 13C NMR (100
MHz, CDCl3) δ 175.7, 139.7, 134.2, 132.1, 130.0, 129.8,
127.9, 127.7, 118.8, 92.6, 85.5. HRMS (EI) Calcd for
C15H10ClO [M+H]+, 241.0415; found, 241.0408.
δ 8.15 (dd, J = 15.2, 8.4 Hz, 1H), 7.64 (d, J = 7.2 Hz, 2H),
7.53 – 7.44 (m, 1H), 7.40 (dd, J = 15.6, 8.4 Hz, 2H), 7.00
(t, J = 8.0 Hz, 1H), 6.95 – 6.86 (m, 1H) . 13C NMR (100
MHz, CDCl3) δ 172.7, 133.8, 133.7, 133.2, 131.0, 128.7,
119.9, 112.0, 111.8, 105.6, 105.3, 105.1, 99.9, 93.3, 88.2.
HRMS (EI) Calcd for C15H9F2O [M+H]+, 243.0616; found,
243.0625.
3-Phenyl-1-(4-(trifluoromethyl)phenyl)prop-2-yn-1-
1
one(2f): White solid. mp 71−72 °C. H NMR (400 MHz,
CDCl3) δ 8.32 (d, J = 7.6 Hz, 2H), 7.78 (d, J = 7.6 Hz, 2H),
7.70 (d, J = 7.6 Hz, 2H), 7.46 (dt, J = 14.8, 8.0 Hz, 3H) .
13C NMR (100 MHz, CDCl3) δ 176.8, 139.4, 133.2, 131.3,
129.8, 128.8, 125.8, 125.7, 119.7, 94.5, 86.6. HRMS (EI)
Calcd for C16H10F3O [M+H]+, 275.0678; found, 275.0682.
1-(Naphthalen-1-yl)-3-phenylprop-2-yn-1-one
(2o):
1
White solid. mp 92−93 °C. H NMR (400 MHz, CDCl3) δ
9.24 (d, J = 8.4 Hz, 1H), 8.63 (d, J = 8.0 Hz, 1H), 8.05 (d,
J = 8.0 Hz, 1H), 7.88 (d, J = 8.4 Hz, 1H), 7.66 (t, J = 7.6
Hz, 4H), 7.55 (q, J = 7.2 Hz, 3H), 7.43 (ddd, J = 14.8, 8.0,
6.4 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ 179.6, 135.2,
134.4, 133.8, 132.9, 132.9, 130.7, 130.7, 128.9, 128.6,
128.5, 126.7, 125.8, 124.4, 120.4, 91.7, 88.3. HRMS (EI)
Calcd for C19H13O [M+H]+, 257.0961; found, 257.0955.
4-(3-Phenylpropioloyl)benzonitrile(2g): White solid. mp
1
140−142 °C. H NMR (400 MHz, CDCl3) δ 8.23 (d, J =
8.4 Hz, 2H), 7.75 (d, J = 8.4 Hz, 2H), 7.64 –7.57 (m, 2H),
7.45 (dd, J = 10.8, 4.4 Hz, 1H), 7.37 (t, J= 7.6 Hz, 2H) .
13C NMR (100 MHz, CDCl3) δ 176.1, 139.4, 133.2, 132.4,
131.3, 129.7, 128.7, 119.3, 117.8,117.0, 95.0, 86.3. HRMS
(EI) Calcd for C16H10NO [M+H]+, 232.0757; found,
232.0749.
3-Phenyl-1-(quinolin-6-yl)prop-2-yn-1-one (2p): White
solid. mp 123−125 °C. 1H NMR (400 MHz, CDCl3) δ 8.93
(dd, J = 4.0, 1.6 Hz, 1H), 8.62 (d, J = 1.6 Hz, 1H), 8.35 (dd,
J = 8.8, 2.0 Hz, 1H), 8.22 (d, J = 8.4 Hz, 1H), 8.08 (d, J =
8.8 Hz, 1H), 7.66 –7.60 (m, 2H), 7.40 (dd, J = 7.6, 3.6 Hz,
2H), 7.34 (t, J = 7.2 Hz, 2H). 13C NMR (100 MHz, CDCl3)
δ 177.1, 153.0, 150.5, 137.8, 134.6, 133.1, 132.0, 131.0,
130.1, 128.8, 127.8, 127.3, 122.1, 119.8, 93.8, 86.9;
HRMS (EI) Calcd for C18H12NO [M+H]+, 258.0913; found,
258.0917.
Methyl 4-(3-phenylpropioloyl)benzoate(2h): White solid.
mp 104−105 °C. 1H NMR (400 MHz, CDCl3) δ 8.34 –8.17
(m, 2H), 8.19 –8.08 (m, 2H), 7.67 (dd, J= 8.4, 1.2 Hz, 2H),
7.52 –7.46 (m, 1H), 7.45 –7.37 (m, 2H), 3.93 (s, 3H) . 13C
NMR (100 MHz, CDCl3) δ 177.2, 166.1, 139.99, 134.7,
133.1, 129.8, 129.4, 129.4, 128.7, 119.8, 94.2, 86.8, 52.5.
HRMS (EI) Calcd for C17H13O3 [M+H]+, 265.0859; found,
265.0848.
3-(4-Methoxyphenyl)-1-phenylprop-2-yn-1-one
(3a):
1
White solid. mp 81−82 °C. H NMR (400 MHz, CDCl3) δ
8.23 – 8.11 (m, 2H), 7.62 – 7.51 (m, 3H), 7.46 (t, J = 7.6
Hz, 2H), 6.86 (d, J = 8.8 Hz, 2H), 3.78 (s, 3H). 13C NMR
(100 MHz, CDCl3) δ 177.7, 161.5, 136.8, 134.9, 133.7,
129.2, 128.4, 114.2, 111.5, 94.2, 86.7, 55.2. HRMS (EI)
Calcd for C16H13O2 [M+H]+, 237.0910; found, 237.0912.
1-(3-Fluorophenyl)-3-phenylprop-2-yn-1-one
(2i):
1
White solid. mp 85−86 °C. H NMR (400 MHz, CDCl3) δ
8.04 (dt, J = 7.6, 1.2 Hz, 1H), 7.87 (dt, J = 9.2, 2.0 Hz, 1H),
7.72 – 7.66 (m, 2H), 7.54 – 7.49 (m, 2H), 7.47 – 7.41 (m,
2H), 7.37-7.31 (m, 1H). 13C NMR (100 MHz, CDCl3) δ
176.6, 164.0, 161.5, 139.0, 138.9, 133.2, 131.1, 130.4,
130.3, 128.8, 125.5, 125.4, 121.3, 121.1, 119.8, 116.1,
1-(4-Methylphenyl)-1-phenylprop-2-yn-1-one
(3b):
115.9, 93.8, 86.6. HRMS (EI) Calcd for C15H10FO [M+H]+, White solid. mp 69−71 °C. H NMR (400 MHz, CDCl3) δ
1
225.0710; found, 225.0715.
8.27 – 8.18 (m, 2H), 7.67 – 7.56 (m, 3H), 7.51 (t, J = 7.6
Hz, 2H), 7.24 (d, J = 8.0 Hz, 2H), 2.41 (s, 3H). 13C NMR
(100 MHz, CDCl3) δ 178.1, 141.5, 136.9, 134.0, 133.2,
133.0, 129.5, 128.5, 116.9, 93.8, 86.7, 21.7. HRMS (EI)
Calcd for C16H13O [M+H]+, 221.0961; found, 221.0965.
1-(3-Chlorophenyl)-3-phenylprop-2-yn-1-one
(2j):
1
White solid. mp 92−93 °C. H NMR (400 MHz, CDCl3) δ
8.16 (d, J= 1.6 Hz, 1H), 8.10 (d, J= 7.6 Hz, 1H), 7.72 –
7.64 (m, 2H), 7.59 (dd, J= 8.0, 0.8 Hz, 1H), 7.45 (dq, J=
12.0, 7.2 Hz, 4H). 13C NMR (100 MHz, CDCl3) δ 176.6,
138.4, 135.0, 134.1, 133.2, 131.1, 130.0, 129.4, 128.8,
127.7, 119.8, 94.0, 86.5. HRMS (EI) Calcd for
C15H10ClO [M+H]+, 241.0415; found, 241.0411.
1-(4-Ethylphenyl)-1-phenylprop-2-yn-1-one (3c): White
solid. mp 77−78 °C. 1H NMR (400 MHz, CDCl3) δ 8.14 (d,
J = 8.0 Hz, 2H), 7.71 (s, 2H), 7.54 – 7.26 (m, 5H), 2.75 (s,
2H), 1.28 (d, J = 7.2 Hz, 3H). 13C NMR (100 MHz,
CDCl3) δ 176.7, 150.4, 133.7, 132.0, 129.7, 128.8, 127.6,
127.1, 119.2, 91.6, 85.9, 28.1, 14.1. HRMS (EI) Calcd for
C17H15O [M+H]+, 235.1117; found, 235.1122.
1-(3-Nitrophenyl)-3-phenylprop-2-yn-1-one
(2k):
Yellow solid. mp 120−122 °C. 1H NMR (400 MHz,
CDCl3) δ 9.03 (t, J = 2.0 Hz, 1H), 8.54 – 8.46 (m, 2H),
7.80 – 7.72 (m, 3H), 7.56 – 7.44 (m, 3H). 13C NMR (100
MHz, CDCl3) δ 175.5, 148.5, 138.1, 134.6, 133.3, 131.5,
129.9, 128.2, 124.6, 119.4, 95.4, 86.2. HRMS (EI) Calcd
for C15H10NO3 [M+H]+, 252.0655; found, 252.0647.
3-(4-(tert-Butyl)phenyl)-1-phenylprop-2-yn-1-one(3d):
1
White solid. mp 61−62 °C. H NMR (400 MHz, CDCl3) δ
8.27 –8.18 (m, 2H), 7.64 –7.57 (m, 3H), 7.49 (dd, J = 10.4,
4.8 Hz, 2H), 7.45 –7.38 (m, 2H), 1.32 (s, 9H). 13C NMR
(100 MHz, CDCl3) δ 177.7, 154.3, 136.7, 133.8, 132.8,
129.3, 128.4, 125.5, 116.7, 93.6, 86.6, 34.8, 30.8. HRMS
1-(2-Chlorophenyl)-3-phenylprop-2-yn-1-one
(2l):
1
White solid. mp 62−63 °C. H NMR (400 MHz, CDCl3) δ
8
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