10.1002/adsc.201801707
Advanced Synthesis & Catalysis
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1
Colorless oil, yield (25.0 mg, 88%); H NMR (500 MHz,
CDCl3): δ=2.50 (m, 2H), 2.81 (t, 2H), 6.17 (t, 1H), 7.13–
7.41 (m, 15H); 13C NMR (125 MHz, CDCl3): δ=31.60,
36.15, 125.82, 126.85, 126.88, 127.19, 128.05, 128.11,
128.27, 128.50, 128.77, 129.79, 140.07, 141.65, 142.27,
142.64; GC-MS: M+=284.
Brown oil, yield (19.1 mg, 75%); H NMR (500 MHz,
CDCl3): δ=1.69 (m, 4H), 2.65 (t, 2H), 2.74 (t, 2H), 7.15–
7.31 (m, 7H), 8.12 (d, 2H); 13C NMR (125 MHz, CDCl3):
δ=30.44, 30.85, 35.55, 35.66, 35.70, 123.61, 125.85,
128.36, 129.15, 142.07, 146.42, 150.38; GC-MS: M+=255.
1,3-Diphenylpropene (2a)
Colorless oil, yield (14.7 mg, 76%); H NMR (500 MHz,
1
1-tert-Butyl-4-(4-phenyl-but-1-enyl)-benzene (1c)
1
Colorless oil, yield (22.2 mg, 84%); H NMR (500 MHz,
CDCl3): δ=3.56 (d, 2H), 6.37 (dt, J=15.5Hz, 6.8 Hz, 1H),
6.45 (d, J=15.5Hz, 1H), 7.21–7.36 (m, 10H); 13C NMR
(125 MHz, CDCl3): δ=39.35, 126.13, 126.18, 127.09,
128.49, 128.67, 129.24, 131.10, 137.51, 140.18; GC-MS:
M+=194.
CDCl3): δ=1.30 (s, 9H), 2.50 (q, 2H), 2.75 (t, 2H), 6.23 (dt,
J=15.5Hz, 6.8Hz, 1H), 6.37 (d, J=15.5Hz, 1H), 7.18–7.32
(m, 9H); 13C NMR (125 MHz, CDCl3): δ=31.05, 34.23,
34.61, 35.71, 125.13, 125.42, 125.58, 128.06, 128.22,
128.93, 129.83, 134.71, 141.57; GC-MS: M+=264.
4-Methoxy-4-(4-phenyl-but-3-enyl)-benzene (2b)
1
White solid, yield (20.7 mg, 87%); H NMR (500 MHz,
1-Methoxy-4-(4-phenyl-but-1-enyl)-benzene (1d)
Colorless oil, yield (17.8 mg, 75%); H NMR (500 MHz,
1
CDCl3): δ=2.50 (m, 2H), 2.74 (t, 2H), 3.80 (s, 3H), 6.27 (dt,
CDCl3): δ=2.53 (m, 2H), 2.80 (t, 2H), 3.82 (s, 3H), 6.14 (dt, J=15.5Hz, 6.8Hz, 1H), 6.40 (d, J=5.5Hz, 1H), 6.86 (dd,
J=15.5Hz, 6.8Hz, 1H), 6.37 (d, J=15.5Hz, 1H), 6.85 (d,
2H), 7.21–7.33 (m, 7H); 13C NMR (125 MHz, CDCl3):
δ=35.10, 36.29, 55.54, 114.19, 126.08, 127.32, 128.08,
128.58, 128.72, 129.97, 130.85, 142.13, 159.02; GC-MS:
M+=238.
2H), 7.14 (dd, 2H), 7.19–7.35 (m, 7H); 13C NMR (125
MHz, CDCl3): δ=35.36, 35.49, 55.66, 114.19, 126.37,
127.28, 128.86, 129.74, 130.48, 130.72, 134.26, 138.18,
158.24; GC-MS: M+=238.
4-Mmethyl-4-(4-phenyl-but-3-enyl)-benzene (2c)
1
White solid, yield (19.5 mg, 88%); H NMR (500 MHz,
1-Methyl-4-(4-phenyl-but-1-enyl)-benzene (1e)
Colorless oil, yield (16.4 mg, 74%); H NMR (500 MHz,
1
CDCl3): δ=2.49 (s, 3H), 2.68 (q, 2H), 2.91 (t, 2H), 6.44 (dt,
CDCl3): δ=2.38 (s, 3H), 2.58 (m, 2H), 2.82 (t, 2H), 6.26 (dt, J=15.5Hz, 6.8Hz, 1H), 6.56 (d, J=15.5Hz, 1H), 7.27–7.50
J=15.5Hz, 6.8Hz, 1H), 6.42 (d, J=15.5Hz, 1H), 7.14 (d,
2H), 7.23–7.36 (m, 5H); 13C NMR (125 MHz, CDCl3):
δ=20.85, 34.59, 35.70, 125.58, 125.63, 128.07, 128.21,
128.67, 128.91, 129.96, 134.71, 136.36, 141.58; GC-MS:
M+=222.
(m, 9H); 13C NMR (125 MHz, CDCl3): δ=21.24, 35.24,
35.69, 126.24, 127.14, 128.59, 128.72, 129.29, 130.39,
130.53, 135.55, 138.04, 138.94; GC-MS: M+=222.
3-Methyl-4-(4-phenyl-but-3-enyl)-benzene (2d)
1
White solid, yield (18.6 mg, 84%); H NMR (500 MHz,
CDCl3): δ=2.35 (s, 3H), 2.52 (q, 2H), 2.74 (t, 2H), 6.29 (dt,
J=15.5Hz, 6.8Hz, 1H), 6.42 (d, J=15.5Hz, 1H), 7.05 (m,
3H), 7.20–7.35 (m, 6H); 13C NMR (125 MHz, CDCl3):
δ=21.65, 29.95, 35.14, 36.08, 125.71, 126.25, 126.87,
127.16, 128.50, 128.73, 129.54, 130.38, 130.55, 138.05,
138.15, 141.98; GC-MS: M+= 22.
1-Chloro-4-(4-phenyl-but-1-enyl)-benzene (1f)
Colorless oil, yield (17.4 mg, 72%); H NMR (500 MHz,
1
CDCl3): δ=2.56 (m, 2H), 2.82 (t, 2H), 6.26 (dt, J=15.5Hz,
6.8Hz, 1H), 6.37 (d, J=15.5Hz, 1H), 7.243–7.35 (m, 9H);
13C NMR (125 MHz, CDCl3): δ=34.78, 35.74, 127.17,
128.37, 128.43, 128.59, 129.24, 130.68, 132.48, 136.21,
141.57, 136.36, 141.58; GC-MS: M+=242.
2-Methyl-4-(4-phenyl-but-3-enyl)-benzene (2e)
1
White solid, yield (13.7 mg, 62%); H NMR (500 MHz,
1-Trifluoromethyl-4-(4-phenyl-but-1-enyl)-benzene (1g)
White solid, yield (19.6 mg, 71%); H NMR (500 MHz,
1
CDCl3): δ=2.35 (s, 3H), 2.49 (q, 2H), 2.77 (t, 2H), 6.32 (dt,
J=15.5Hz, 6.8Hz, 1H), 6.42 (d, J=15.5Hz, 1H), 7.05 (m,
3H), 7.13–7.36 (m, 9H); 13C NMR (125 MHz, CDCl3):
δ=19.33, 33.20, 33.65, 125.96, 125.99, 126.02, 126.93,
128.49, 128.83, 130.12, 130.18, 130.29, 135.90, 139.93;
GC-MS: M+=222.
CDCl3): δ=2.58 (q, 2H), 2.80 (t, 2H), 6.38 (dt, J=15.5Hz,
6.8Hz, 1H), 6.43 (d, J=15.5Hz, 1H), 7.22–7.33 (m, 5H),
7.42 (d, 2H), 7.53 (d, 2H); 13C NMR (125 MHz, CDCl3):
δ=29.95, 35.03, 35.87, 125.68, 125.71, 126.27, 126.36,
128.67, 128.70, 129.56, 133.05, 141.47, 141.68; GC-MS:
M+=276.
4-Trifluoromethyl-4-(4-phenyl-but-3-enyl)-benzene (2f)
1
White solid, yield (27.0 mg, 98%); H NMR (500 MHz,
1-(Naphtha-2-yl)-5-phenyl-2-butene (1h)
White solid, yield (20.4 mg, 79%); H NMR (500 MHz,
1
CDCl3): δ=2.55 (q, 2H), 2.84 (t, 2H), 6.24 (dt, J=15.5Hz,
6.8Hz, 1H), 6.43 (d, J=15.5Hz, 1H), 7.22–7.33 (m, 7H),
7.55 (d, 2H); 13C NMR (125 MHz, CDCl3): δ=34.42, 35.67,
125.27, 125.30, 126.01, 127.11, 128.52, 128.78, 129.10,
130.93, 137.49, 145.78; GC-MS: M+=276.
CDCl3): δ=2.61 (q, 2H), 2.865 (t, 2H), 6.43 (dt, J=15.5Hz,
6.8Hz, 1H), 6.59 (d, J=15.5Hz, 1H), 7.22–7.35 (m, 5H),
7.45 (m, 2H), 7.59 (dd, 1H), 7.69 (s, 1H), 7.81 (t, 3H); 13
C
NMR (125 MHz, CDCl3): δ=34.69, 35.67, 123.39, 125.19,
125.25, 125.67, 125.88, 127.38, 127.60, 127.81, 128.13,
128.24, 130.22, 130.32, 132.53, 133.51, 135.00, 141.52;
GC-MS: M+=258.
(2-Cyclohexylvinyl)benzene (2g)
1
Colorless oil, yield (10.9 mg, 59%); H NMR (500 MHz,
CDCl3): δ=1.20–1.32 (m, 5H), 1.69–1.78 (m, 5H), 2.13 (m,
1H), 6.20 (dd, J=15.5Hz, 6.8Hz, 1H), 6.33 (d, J=15.5Hz,
1H), 7.18 (m, 1H), 7.19–7.36 (m, 4H); 13C NMR (125
1-Nitro-4-(4-phenylbutyl)-benzene (1i)
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