2842
J.-x. Wang et al.
PAPER
13C NMR (100 MHz, CDCl3, TMS): d = 134.91, 118.06, 70.65,
41.92, 36.80, 31.80, 29.30, 25.62, 22.60, 14.06.
13C NMR (100MHz, CDCl3, TMS): d = 147.59, 133.63, 128.15,
126.59, 124.73, 119.49, 73.58, 48.42, 29.89.
MS (EI, 70 eV): m/z (%) = 139 (0.6) [M+ – OH], 115 (13.7), 97
MS (EI, 70 eV): m/z (%) = 162 (0.3) [M+], 145 (0.9), 121 (29.9), 105
(38.3), 69 (15.9), 55 (100.0), 41 (55.4).
(62.9), 77 (12.0), 51 (9.7), 43 (100.0).
1-(9-Anthryl)but-3-en-1-ol (3j)
1,1-Diphenylbut-3-en-1-ol (5b)
Oil.35
Oil.25
IR: 3410, 3070, 2923, 2853, 1723, 1666, 1446, 1315, 1285, 1036,
917, 735 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 8.64–7.22 (m, 9 H), 6.30 (q,
J = 5.2 Hz, 1 H), 5.98–5.89 (m, 1 H), 5.26–5.12 (m, 2 H), 3.23–2.82
(m, 2 H), 2.23 (s, 1 H).
13C NMR (100 MHz, CDCl3, TMS): d = 138.05, 135.18, 133.95,
131.64, 129.32, 129.20, 128.19, 125.56, 124.76, 118.00, 70.61,
42.06.
IR: 3549, 3475, 3068, 2930, 1817, 1639, 1440, 1171, 998, 918 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 7.46–7.19 (m, 10 H), 5.71–
5.60 (m, 1 H), 5.26–5.16 (m, 2 H), 3.09–3.06 (m, 2 H), 2.55 (s, 1 H).
13C NMR (100 MHz, CDCl3): d = 146.46, 133.40, 128.17, 126.85,
125.95, 120.55, 76.84, 46.28.
MS (EI, 70 eV): m/z (%) = 224 (0.1) [M+], 207 (1.5), 183 (79.6), 165
(2.0), 105 (100.0), 91 (11.4), 77 (66.0), 51 (16.3), 39 (13.3).
MS (EI, 70 eV): m/z (%) = 248 (8.4) [M+], 231 (0.1), 207 (51.5), 178
(34.2), 152 (57.0), 137 (3.9), 123 (96.8), 106 (6.3), 95 (10.2), 73
(21.2), 61 (16.3), 43 (100.0).
4-Phenylhex-1-en-4-ol (5c)
Oil.37
IR: 3474,3068, 3028, 2972, 2934, 1638, 1602, 1493, 1445, 978,
918, 762, 702, 567 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 7.40–7.21 (m, 5 H), 5.62–
5.53 (m, 1 H), 5.16–5.09 (m, 2 H), 2.75–2.46 (m, 2 H), 2.02 (s, 1 H),
1.89–1.77 (q, 2 H), 0.76 (t, J = 7.6 Hz, 3 H).
13C NMR (100 MHz, CDCl3, TMS): d = 145.71, 133.56, 128.03,
126.39, 125.37, 119.54, 75.97, 46.89, 35.22, 7.81.
MS (EI, 70 eV): m/z (%) = 159 (0.6) [M+ – OH], 147 (0.6), 135
(40.2), 117 (3.5), 105 (21.8), 91 (5.5), 77 (23.2), 57 (100.0), 41
(22.8), 39 (34.1).
1-(2-Thienyl)but-3-en-1-ol (3k)
Oil.36
IR: 3374, 3075, 2932, 2905, 1641, 1436, 1034, 919, 852 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 7.25–7.24 (m, 1 H), 6.99–
6.96 (m, 2 H), 5.88–5.78 (m, 1 H), 5.22–5.15 (m, 2 H), 4.99 (t, J =
6.4 Hz, 1 H), 2.64–2.60 (m, 2 H), 2.17 (s, 1 H).
13C NMR (100 MHz, CDCl3, TMS): d = 147.75, 133.79, 126.62,
124.56, 123.67, 118.84, 69.33, 43.76.
MS (EI, 70 eV): m/z (%) = 154 (1.1) [M+], 137 (9.4), 113 (100.0),
85 (72.9), 83 (2.7), 58 (7.0), 45 (58.3), 41 (27.3), 39 (54.1).
4-Methylnon-1-en-4-ol (5d)
Oil.25
1-(2-Furyl)but-3-en-1-ol (3l)
IR: 3392, 3073, 2935, 1642, 1454, 1149, 1002, 917 cm–1.
Oil.25,26
1H NMR (400 MHz, CDCl3, TMS): d = 6.08–5.87 (m, 1 H), 5.27–
5.18 (m, 2 H), 2.35–2.28 (m, 2 H), 1.53–1.41 (m, 9 H), 1.28 (s, 3 H),
1.04–0.97 (t, 3 H).
13C NMR (100 MHz, CDCl3, TMS): d = 134.10, 118.58, 72.17,
46.23, 41.81, 32.36, 26.69, 23.50, 22.62, 14.03.
MS (EI, 70 eV): m/z (%) = 139 (11.6) [M+ – OH], 115 (23.2), 99
(100.0), 83 (12.1), 71 (55.3), 55 (34.3), 43 (92.4).
IR: 3370, 3078, 2918, 1841, 1643, 1431, 1029, 920 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 7.38–7.26 (m, 1 H), 6.34–
6.25 (m, 2 H), 5.86–5.77 (m, 1 H), 5.20–5.13 (m, 2 H), 4.75 (t, J =
6.8 Hz, 1 H), 2.67–2.59 (m, 2 H), 2.07 (s, 1 H).
13C NMR (100 MHz, CDCl3, TMS): d = 155.95, 141.97, 133.64,
118.60, 110.12, 106.08, 66.88, 40.04.
MS (EI, 70 eV): m/z (%) = 138 (3.4) [M+], 121 (5.3), 97 (100.0), 84
(24.7), 69 (16.4), 55 (24.5), 41 (38.5), 39 (36.2).
1-(Prop-2-enyl)cyclohexan-1-ol (5e)
Oil.25,26
1-Phenylhexa-1,5-dien-3-ol (3m)
IR: 3403, 3073, 2930, 1643, 1445, 1143, 969, 913 cm–1.
Oil.25,26
1H NMR (400 MHz, CDCl3, TMS): d = 5.94–5.83 (m, 1 H), 5.16–
5.08 (m, 2 H), 2.21 (d, J = 7.6 Hz, 2 H), 1.64–1.40 (m, 10 H), 1.31–
1.25 (m, 1 H).
13C NMR (100 MHz, CDCl3, TMS): d = 133.69, 118.66, 70.91,
46.66, 37.35, 25.73, 22.15.
MS (EI, 70 eV): m/z (%) = 123 (0.9) [M+ – OH], 99 (62.3), 81
(86.6), 69 (10.2), 55 (65.5), 41 (100.0).
IR: 3374, 3070, 2925, 1640, 1438, 998, 915, 740, 687 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 7.39–7.21 (m, 5 H), 6.60 (d,
J = 16.0 Hz, 1 H), 6.24 (dd, J = 16.0, 6.4 Hz, 1 H), 5.91–5.80 (m, 1
H), 5.21–5.14 (m, 2 H), 4.36 (q, J = 6.4 Hz, 1 H), 2.46–2.34 (m, 2
H), 1.98 (s, 1 H).
13C NMR (100 MHz, CDCl3, TMS): d = 136.60, 133.98, 131.48,
130.36, 128.55, 127.64, 126.46, 118.53, 71.69, 41.98.
MS (EI, 70 eV): m/z (%) = 174 (4.6) [M+], 157 (5.3), 133 (75.3), 115
(31.8), 91 (15.0), 77 (35.7) 55 (100.0), 39 (52.7).
1-(Prop-2-enyl)cyclopentan-1-ol (5f)
Oil.2b
IR: 3386, 3074, 2954, 1829, 1640, 1437, 1192, 995, 913 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 5.95–5.85 (m, 1 H), 5.16–
5.12 (m, 2 H), 2.34 (d, J = 7.6 Hz, 2 H), 1.85–1.56 (m, 9 H).
13C NMR (100 MHz, CDCl3, TMS): d = 134.53, 118.59, 73.29,
45.83, 39.38, 23.83.
2-Phenylpent-4-en-2-ol (5a)
Oil.25,26
IR: 3425, 3070, 2975, 2925, 1646, 1440, 1364, 1059, 922 cm–1.
1H NMR (400 MHz, CDCl3, TMS): d = 7.47–7.21 (m, 5 H), 5.60–
5.56 (m, 1 H), 5.17–5.09 (m, 2 H), 2.71–2.44 (m, 2 H), 2.00 (s, 1 H),
1.54 (s, 3 H).
MS (EI, 70 eV): m/z (%) = 126 (0.7) [M+], 109 (0.6), 85 (100.0), 67
(77.8), 55 (51.9), 41 (57.2), 39 (51.1).
Synthesis 2005, No. 17, 2838–2844 © Thieme Stuttgart · New York