H
Z. Zhang et al.
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Synthesis
1H NMR (400 MHz, CDCl3): δ = 7.45 (d, J = 8.0 Hz, 2 H), 7.34 (t, J = 7.2
Hz, 2 H), 7.23 (dd, J = 8.4, 16.4 Hz, 2 H), 7.20–7.12 (m, 2 H), 7.02 (d,
J = 7.2 Hz, 1 H), 6.44 (q, J = 2.8 Hz, 1 H), 2.32 (s, 3 H), 2.23 (d, J = 2.8 Hz,
3 H).
1H NMR (400 MHz, CDCl3): δ = 7.80 (d, J = 7.8 Hz, 1 H), 7.78–7.86 (m, 1
H), 7.74 (d, J = 8.2 Hz, 1 H), 7.56 (d, J = 6.6 Hz, 1 H), 7.51–7.43 (m, 4 H),
7.42 (t, J = 7.8 Hz, 1 H), 7.36 (t, J = 7.8 Hz, 2 H), 7.23 (t, J = 7.8 Hz, 1 H),
7.21 (q, J = 3.0 Hz, 1 H), 2.27 (d, J = 2.6 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 206.8, 138.3, 136.4, 134.4, 128.6,
128.4, 127.9, 127.5, 127.0, 125.8, 124.1, 104.3, 96.6, 21.4, 16.8.
13C{1H} NMR (100 MHz, CDCl3): δ = 208.2, 136.4, 134.0, 130.9, 130.6,
128.7, 128.5, 127.6, 127.0, 126.2, 125.9, 125.73, 125.68, 125.6, 122.7,
103.4, 93.4, 16.9.
1-(4-Methylphenyl)-3-phenylbuta-1,2-diene (2d)6h
1-(Naphthylen-2-yl)-3-phenylbuta-1,2-diene (2k)6h
Yield: 0.091 g (83%); yellow oil.
Yield: 0.10 g (78%); yellow solid; mp 40–42 °C.
1H NMR (400 MHz, CDCl3): δ = 7.46–7.44 (m, 2 H), 7.34–7.30 (m, 2 H),
7.25–7.21 (m, 3 H), 7.13 (d, J = 8.0 Hz, 2 H), 6.46 (q, J = 2.8 Hz, 1 H),
2.33 (s, 3 H), 2.21 (d, J = 2.8 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 206.5, 136.7, 136.5, 131.6, 129.5,
128.4, 126.9, 126.8, 125.8, 104.4, 96.4, 21.2, 16.8.
1H NMR (400 MHz, CDCl3): δ = 7.79–7.70 (m, 4 H), 7.52–7.50 (m, 3 H),
7.48–7.42 (m, 2 H), 7.36–7.32 (m, 2 H), 7.25–7.22 (m, 1 H), 6.66 (q,
J = 2.6 Hz, 1 H), 2.27 (d, J = 2.6 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 207.4, 136.3, 133.7, 132.7, 132.0,
128.5, 128.3, 127.69, 127.68, 127.1, 126.2, 125.9, 125.63, 125.62,
124.8, 104.7, 96.9, 16.8.
1-(2-Methoxyphenyl)-3-phenylbuta-1,2-diene (2e)6h
Yield: 0.093 g (79%); yellow oil.
2-Phenylnona-2,3-diene (2l)6h
1H NMR (400 MHz, CDCl3): δ = 7.47–7.45 (m, 2 H), 7.38–7.30 (m, 3 H),
7.24–7.18 (m, 2 H), 6.90–6.86 (m, 3 H), 3.86 (s, 3 H), 2.22 (d, J = 3.3 Hz,
3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 207.2, 156.1, 136.6, 128.4, 128.1,
127.8, 126.8, 125.7, 122.8, 120.7, 111.0, 103.7, 90.5, 55.6, 16.8.
Yield: 0.077 g (83%); colorless oil.
1H NMR (400 MHz, CDCl3): δ = 7.43–7.41 (m, 2 H), 7.33–7.25 (m, 2 H),
7.19–7.16 (m, 1 H), 5.46–5.41 (m, 1 H), 2.13–2.10 (m, 2 H), 2.08 (d,
J = 2.6 Hz, 3 H), 1.54–1.43 (m, 2 H), 1.37–1.28 (m, 4 H), 0.89 (t, J = 7.4
Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 204.1, 137.8, 128.2, 126.2, 125.6,
100.2, 93.1, 31.4, 28.93, 28.88, 22.5, 17.2, 14.1.
1-(2-Chlorophenyl)-3-phenylbuta-1,2-diene (2f)6h
Yield: 0.106 g (88%); yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.47–7.41 (m, 3 H), 7.37–7.32 (m, 3 H),
7.26–7.22 (m, 1 H), 7.18–7.11 (m, 2 H), 6.91 (q, J = 2.8 Hz, 1 H), 2.23
(d, J = 2.6 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 207.8, 135.9, 132.2, 129.8, 128.5,
128.4, 128.0, 127.2, 126.8, 125.8, 104.8, 93.0, 16.6.
Phenyl-3-trimethylsilylbuta-1,2-diene (2m)6h
Yield: 0.089 g (88%); colorless oil.
1H NMR (400 MHz, CDCl3): δ = 7.28–7.20 (m, 4 H), 7.14–7.10 (m, 1 H),
5.82 (q, J = 2.7 Hz, 1 H), 1.80 (d, J = 2.6 Hz, 3 H), 0.15 (s, 9 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 205.6, 136.1, 128.5, 125.9, 125.7,
1-(4-Chlorophenyl)-3-phenylbuta-1,2-diene (2g)6h
95.5, 88.3, 15.1, –1.7.
Yield: 0.105 g (87%); yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.45–7.43 (m, 2 H), 7.35–7.32 (m, 2 H),
7.30–7.22 (m, 5 H), 6.44 (q, J = 2.6 Hz, 1 H), 2.22 (d, J = 2.6 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 206.9, 136.0, 133.1, 132.6, 128.8,
128.5, 128.0, 127.2, 125.8, 105.0, 95.7, 16.7.
1-(4-Methylphenyl)-3-trimethylsilylbuta-1,2-diene (2n)6h
Yield: 0.088 g (81%); colorless oil.
1H NMR (400 MHz, CDCl3): δ = 7.12–7.07 (m, 4 H), 5.80 (q, J = 3.0 Hz, 1
H), 2.32 (s, 3 H), 1.81 (d, J = 3.3 Hz, 3 H), 0.14 (s, 9 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 205.6, 135.4, 133.0, 129.2, 125.8,
95.4, 88.1, 21.1, 15.2, –1.7.
1-(4-Bromophenyl)-3-phenylbuta-1,2-diene (2h)
Yield: 0.125 g (88%); yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.45–7.43 (m, 2 H), 7.35–7.32 (m, 2 H),
7.30–7.22 (m, 5 H), 6.44 (q, J = 2.7 Hz, 1 H), 2.24 (d, J = 2.6 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 206.9, 136.0, 133.1, 132.6, 128.8,
128.5, 128.0, 127.2, 125.8, 105.0, 95.7, 16.7.
1-(4-Chlorophenyl)-3-trimethylsilylbuta-1,2-diene (2o)6h
Yield: 0.103 g (87%); colorless oil.
1H NMR (400 MHz, CDCl3): δ = 7.23–7.20 (m, 2 H), 7.14–7.11 (m, 2 H),
5.77 (q, J = 3.0 Hz, 1 H), 1.82 (d, J = 2.7 Hz, 3 H), 0.13 (s, 9 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 205.4, 134.7, 131.1, 128.6, 127.0,
96.0, 87.5, 15.0, –1.8.
1-(4-Trifluoromethylphenyl)-3-phenylbuta-1,2-diene (2i)6h
Yield: 0.114 g (83%); yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.56–7.52 (m, 2 H), 7.45–7.39 (m, 4 H),
7.36–7.32 (m, 2 H), 7.25–7.21 (m, 1 H), 6.51 (q, J = 3.3 Hz, 1 H), 2.24
(d, J = 3.4 Hz, 3 H).
13C{1H} NMR (100 MHz, CDCl3): δ = 207.8, 138.5, 135.7, 128.9 (q,
J = 32.5 Hz), 128.6, 127.4, 127.0, 125.9, 125.6 (q, J = 3.9 Hz), 124.2 (q,
J = 270 Hz), 105.3, 95.8, 16.6.
3-(Naphthalen-2-yl)-3-trimethylsilylbuta-1,2-diene (2p)6h
Yield. 0.099 g (79%); white solid; mp 41–43 °C.
1H NMR (400 MHz, CDCl3): δ = 7.77–7.72 (m, 3 H), 7.57 (s, 1 H), 7.45–
7.35 (m, 3 H), 6.00 (q, J = 2.7 Hz, 1 H), 1.85 (d, J = 2.7 Hz, 3 H), 0.18 (s, 9
H).
13C {1H} NMR (100 MHz, CDCl3): δ = 206.1, 133.8, 133.7, 132.1, 128.0,
127.6, 127.4, 126.0, 125.0, 124.4, 124.0, 95.7, 88.8, 15.2, –1.7.
1-(Naphthylen-1-yl)-3-phenylbuta-1,2-diene (2j)6h
Yield: 0.103 g (80%); yellow solid; mp 39–41 °C.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–K