The Journal of Organic Chemistry
NOTE
(dt, J = 8.8, 2.6 Hz, 2 H), 3.84 (s, 3 H). 13C NMR (100 MHz, CDCl3) δ
162.1 (d, J = 245.5 Hz), 159.1, 136.9 (d, J = 3.1 Hz), 132.8, 128.2 (d, J =
7.9 Hz), 128.0, 115.5 (d, J = 21.4 Hz), 114.3, 55.3.
H), 7.53-7.45 (m, 4 H), 7.39-7.35(m, 1 H). 13C NMR (100 MHz,
CDCl3): δ 140.7, 140.2, 140.0, 138.0, 133.7, 132.7, 128.8, 128.5, 128.2,
127.7, 127.6, 127.5, 127.4, 127.1, 126.3, 126.0, 125.7, 125.4.
2-(4-Butylphenyl)naphthalene (4h) (CAS no. 1075754-29-8). 1H
NMR (400 MHz, CDCl3): δ 8.02 (d, J = 1.3 Hz, 1 H), 7.89-7.83 (m, 3
H), 7.73 (dd, J = 8.5, 1.8 Hz, 1 H), 7.65-7.62 (m, 2 H), 7.50-7.43 (m, 2
H), 7.28 (d, J = 8.2 Hz, 2 H), 2.67 (t, J = 7.8 Hz, 2 H), 1.65 (m, 2 H), 1.40
(m, 2 H), 0.95 (t, J = 7.3 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ
142.2, 138.5, 138.4, 133.7, 132.5, 128.9, 128.3, 128.1, 127.6, 127.2, 126.2,
125.7, 125.6, 125.4, 35.3, 33.6, 22.4, 14.0.
1
4-Cyanobiphenyl (3n) (CAS no. 2920-38-9). H NMR (400 MHz,
CDCl3): δ 7.67-7.59 (m, 4 H), 7.53-7.50(m, 2 H), 7.43-7.39 (m, 2
H), 7.37-7.33 (m, 1 H). 13C NMR (100 MHz, CDCl3): δ 145.7, 139.2,
132.6, 129.1, 128.6, 127.7, 127.2, 118.9, 110.9.
2,6-Diphenylnaphthalene (3o, 3o0) (CAS no. 60706-24-3). 1H NMR
(400 MHz, CDCl3): δ 8.07 (d, J = 1.9 Hz, 2 H), 7.97(d, J = 8.5 Hz, 2 H),
7.79-7.77 (dd, J = 8.5, 1.8 Hz, 2 H), 7.76-7.73(m, 4 H), 7.52-7.47 (m,
4 H), 7.41-7.37 (tt, J = 7.4, 1.2 Hz, 2 H). 13C NMR (100 MHz, CDCl3):
δ 141.1, 138.7, 132.9, 128.9, 128.7, 127.4, 126.0, 125.5.
2-(4-Fluorophenyl)naphthalene (4i) (CAS no. 28396-55-6). 1H
NMR (400 MHz, CDCl3): δ 7.94 (d, J = 1.3 Hz, 1 H), 7.87-7.80
(m, 3 H), 7.65-7.59 (m, 3 H), 7.49- 7.43 (m, 2 H), 7.17-7.09 (m, 2
H). 13C NMR (100 MHz, CDCl3): δ 163.7, 161.3, 137.5, 137.2, 137.1,
133.6, 132.5, 128.9, 128.8, 128.5, 128.1, 127.6, 126.4, 126.0, 125.6, 125.4,
115.8, 115.6.
o-Terphenyl (3p) (CAS no. 84-15-1). 1H NMR (400 MHz, CDCl3): δ
7.51-7.45 (m, 4H), 7.29-7.23 (m, 6H), 7.22-7.18 (m, 4H). 13C NMR
(100 MHz, CDCl3): δ 141.5, 140.6, 130.6, 129.9, 127.8, 127.4, 126.4.
1
Methyl 4-Biphenylcarboxylate (3q) (CAS no. 720-75-2). H NMR
(400 MHz, CDCl3): δ 8.04-8.01(m, 2 H), 7.59-7.52 (m, 4 H), 7.40-
7.36 (m, 2 H), 7.33-7.29 (m, 1 H), 3.86 (s, 3 H). 13C NMR (100 MHz,
CDCl3): δ 167.0, 145.6, 140.0, 130.1, 128.9, 128.1, 127.2, 127.0, 52.1.
5-Phenylbenzo[d][1, 3]dioxole (3r) (CAS no. 24382-05-6). 1H NMR
(400 MHz, CDCl3): δ 7.52-7.49 (m, 2 H), 7.41-7.37 (m, 2 H), 7.32-
7.28 (m, 1 H), 7.07-7.04 (m, 2 H), 6.87 (dd, J = 7.9, 0.5 Hz, 1 H), 5.98
(s, 2 H). 13C NMR (100 MHz, CDCl3): δ 148.1, 147.0, 140.9, 135.6,
128.7, 126.9, 126.8, 120.6, 108.5, 107.7, 101.1.
1-(4-(Naphthalen-2-yl)phenyl)ethanone (4j) (CAS no. 150988-77-
5). 1H NMR (400 MHz, CDCl3): δ 8.08-8.04(m, 3 H), 7.94-7.85 (m,
3 H), 7.81-7.78 (m, 2 H), 7.74 (dd, J = 8.5, 1.9 Hz, 1 H), 7.54-7.48(m,
2 H), 2.64 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ 197.7, 145.6, 137.1,
135.8, 133.5, 133.0, 129.0, 128.7, 128.3, 127.7, 127.4, 126.5, 126.4, 126.3,
125.1, 26.6.
2-(4-(Trifluoromethyl)phenyl)naphthalene (4k) (CAS no. 460743-
71-9). 1H NMR (400 MHz, CDCl3): δ 8.03 (d, J = 1.4 Hz, 1 H), 7.93-
7.84 (m, 3 H), 7.78 (d, J = 8.2 Hz, 2 H), 7.72-7.68 (m, 3 H), 7.54-7.48
(m, 2 H). 13C NMR (100 MHz, CDCl3): δ 144.6, 137.0, 133.5, 133.0,
129.5, 129.2, 128.7, 128.3, 127.7, 127.6, 126.6, 126.5, 126.3, 125.8, 125.7,
125.6, 125.2, 123.0.
Methyl 2-Biphenylcarboxylate (3s) (CAS no. 16605-99-5). 1H NMR
(400 MHz, CDCl3): δ 7.82 (dd, J = 7.7, 1.3 Hz, 1 H), 7.52 (td, J = 7.5, 1.4
Hz, 1 H), 7.42-7.29 (m, 7 H), 3.62 (s, 3 H). 13C NMR (100 MHz,
CDCl3): δ 169.1, 142.4, 141.3, 131.2, 130.8, 130.7, 129.7, 128.3, 128.0,
127.2, 127.1, 51.9.
1
3-(Naphthalen-2-yl)benzenamine (4l) (CAS no. 176034-11-0). H
1
3-Phenylpyridine (3t) (CAS no. 1008-88-4). H NMR (400 MHz,
NMR (400 MHz, CDCl3): δ 8.00 (d, J = 1.5 Hz, 1 H), 7.89-7.81 (m, 3
H), 7.70 (dd, J = 8.5, 1.8 Hz, 1 H), 7.50-7.43 (m, 2 H), 7.24 (dd, J =
14.9, 7.1 Hz, 1 H), 7.11 (ddd, J = 7.7, 1.6, 1.0 Hz, 1 H), 7.01 (t, J = 1.9 Hz,
1 H), 6.68 (ddd, J = 7.9, 2.3, 0.9 Hz, 1 H), 3.72 (s, 2 H). 13C NMR (100
MHz, CDCl3): δ 146.8, 142.3, 138.7, 133.6, 132.6, 129.7, 128.2, 128.1,
127.6, 126.2, 125.8, 125.7, 125.6, 117.9, 114.2, 114.1.
CDCl3): δ 8.85 (d, J = 1.8 Hz, 1 H), 8.59 (dd, J = 4.8, 1.5 Hz, 1 H), 7.87
(dt, J = 7.9, 2.0 Hz 1 H), 7.59-7.56 (m, 2 H), 7.49-7.45 (m, 2 H),
7.42-7.34 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ 148.4, 148.3,
137.8, 136.6, 134.3, 129.0, 128.1, 127.1, 123.5.
1
2-(4-Methoxyphenyl)naphthalene (4b) (CAS no. 59115-45-6). H
2-(Naphthalen-2-yl)benzofuran (4m) (CAS no. 26870-25-7). 1H
NMR (400 MHz, CDCl3): δ 8.36 (d, J = 0.5 Hz, 1 H), 7.91-7.81
(m, 4 H), 7.60-7.54 (m, 2 H), 7.52-7.45 (m, 2 H), 7.30 (td, J = 7.3, 1.5
Hz, 1 H), 7.24 (td, J = 7.3, 1.1 Hz, 1 H), 7.11 (d, J = 0.8, 1 H). 13C NMR
(100 MHz, CDCl3): δ 155.9, 155.0, 133.4, 133.3, 129.3, 128.5, 128.4,
127.8, 127.7, 126.6, 126.4, 124.4, 123.8, 123.0, 122.8, 120.9, 111.2, 101.9.
5-(Naphthalen-2-yl)benzo[d][1, 3]dioxole (4n) (CAS no. 228715-
55-7). 1H NMR (400 MHz, CDCl3): δ 7.97 (d, J = 1.3 Hz, 1 H), 7.91-
7.85 (m, 3 H), 7.69 (dd, J = 8.5, 1.9 Hz, 1 H), 7.54-7.46 (m, 2 H), 7.23-
7.20 (m, 2 H), 6.95 (dd, J = 7.9, 0.5 Hz, 1 H), 6.03 (s, 2 H). 13C NMR
(100 MHz, CDCl3): δ 148.2, 147.2, 138.2, 135.5, 133.7, 132.4, 128.4,
128.1, 127.6, 126.3, 125.8, 125.5, 125.3, 120.9, 108.6, 107.9, 101.2.
1-(Naphthalen-2-yl)naphthalene (4o) (CAS no. 4325-74-0). 1H
NMR (400 MHz, CDCl3): δ 7.94-7.86 (m, 7 H), 7.62 (dd, J = 8.3,
1.8 Hz, 1 H), 7.56-7.46 (m, 5 H), 7.43-7.38 (m, 1 H). 13C NMR (100
MHz, CDCl3): δ 140.2, 138.3, 133.8, 133.4, 132.6, 131.8, 128.7, 128.5,
128.3, 128.1, 127.7, 127.6, 127.2, 126.3, 126.1, 126.0, 125.8, 125.4.
(8R*,9S*,13S*,14S*)-3-(4-Methoxyphenyl)-13-methyl-7,8,9,11,12,
13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one (8)
NMR (400 MHz, CDCl3): δ 7.96 (s, 1 H), 7.87-7.81 (m, 3 H), 7.69
(dd, J = 8.5, 1.8 Hz, 1 H), 7.65-7.61(dt, J = 8.8, 2.6 Hz, 2 H), 7.45 (dd,
J = 6.9, 1.5 Hz, 2 H), 7.00(dt, J = 8.8, 2.6 Hz, 2 H), 3.82 (s, 3 H). 13C
NMR (100 MHz, CDCl3): δ 159.2, 138.1, 133.7, 133.6, 132.3, 128.4,
128.3, 128.0, 127.6, 126.2, 125.6, 125.4, 125.0, 114.3, 55.3.
1
2-m-Tolylnaphthalene (4c) (CAS no. 36821-15-5). H NMR (400
MHz, CDCl3): δ 8.01 (d, J = 1.3 Hz, 1 H), 7.89-7.82 (m, 3 H), 7.72 (dd,
J = 8.5, 1.9 Hz, 1 H), 7.52-7.42 (m, 4 H), 7.35 (t, J = 7.6 Hz, 1 H), 7.17
(d, J = 6.6 Hz, 1 H), 2.43 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ
141.1, 138.7, 138.4, 133.7, 132.6, 128.7, 128.3, 128.2, 128.1, 128.0, 127.6,
126.2, 125.8, 125.7, 125.6, 124.5, 21.6.
1
2-o-Tolylnaphthalene (4d) (CAS no. 66778-24-3). H NMR (400
MHz, CDCl3): δ 7.87-7.83 (m, 3 H), 7.76 (d, J = 0.6 Hz, 1 H), 7.51-
7.45 (m, 3 H), 7.33-7.24 (m, 4 H), 2.30 (s, 3 H). 13C NMR (100 MHz,
CDCl3): δ 141.8, 139.5, 135.5, 133.3, 132.3, 130.3, 130.0, 128.0, 127.8,
127.7, 127.6, 127.5, 127.4, 126.1, 125.9, 125.8, 20.5.
Methyl 4-(Naphthalen-2-yl)benzoate (4e) (CAS no. 205823-29-6).
1H NMR (400 MHz, CDCl3): δ 8.15-8.12 (m, 2 H), 8.07 (d, J = 1.3 Hz,
1 H), 7.93- 7.84 (m, 3 H), 7.79-7.72 (m, 3 H), 7.53-7.47 (m, 2 H), 3.94
(s, 3 H). 13C NMR (100 MHz, CDCl3): δ 167.0, 145.5, 137.2, 133.5, 132.9,
130.1, 128.9, 128.6, 128.3, 127.6, 127.2, 126.5, 126.4, 126.3, 125.2, 52.1.
1
(CAS no. 1019777-25-3). H NMR (400 MHz, CDCl3): δ 7.53-7.49
(m, 2 H), 7.35 (d, J = 1.2 Hz, 2 H), 7.29 (s, 1 H), 6.98-6.94 (m, 2 H),
3.84 (s, 3 H), 2.98 (dd, J = 8.7, 4.0 Hz, 2 H), 2.55-2.44 (m, 2 H), 2.34
(td, J = 11.1, 4.1 Hz, 1 H), 2.18-2.03(m, 3 H), 2.00-1.96 (m, 1 H),
1.67-1.45 (m, 6 H), 0.92 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ
220.8, 159.0, 138.4, 138.3, 136.8, 133.6, 128.0, 127.3, 125.8, 124.2, 114.1,
55.3, 50.5, 48.0, 44.4, 38.2, 35.8, 31.6, 29.7, 29.5, 26.6, 25.8, 21.6, 13.9. IR
(film): 2928, 2864, 1737, 1608, 1518, 1493, 1468, 1455, 1441,
1
2-p-Tolylnaphthalene (4f) (CAS no. 59115-49-0). H NMR (400
MHz, CDCl3):δ8.00(s, 1H), 7.88-7.82 (m, 3 H), 7.72 (dd, J= 8.5, 1.7 Hz,
1H), 7.61(d,J= 8.1 Hz, 2 H), 7.49-7.42 (m, 2 H), 7.27 (d, J= 8.1 Hz, 2 H),
2.40 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ 138.5, 138.2, 137.1, 133.7,
132.5, 129.6, 128.3, 128.1, 127.6, 127.2, 126.2, 125.7, 125.5, 125.4, 21.1.
2-(4-Phenylphenyl)naphthalene (4g) (CAS no. 68862-02-2). 1H
NMR (400 MHz, CDCl3): δ 8.09 (d, J = 1.1 Hz, 1 H), 7.94-7.86
(m, 3 H), 7.83-7.78 (m, 3 H), 7.74-7.71 (m, 2 H), 7.68-7.65 (m, 2
1282, 1245, 1174, 1025, 822 cm-1. [R]25 þ135.2 (c 1.0, CHCl3)
D
{lit.49 [R]20D þ135.0 (c 0.99, CHCl3)}.
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dx.doi.org/10.1021/jo2000034 |J. Org. Chem. 2011, 76, 2338–2344