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X. YE ET AL.
(29), 205 (39), 105 (90), 77 (62), 57 (100). Anal. calc. for C22H26: C, 90.98; H, 9.02.
Found: C, 90.71; H, 9.25%.
(2E,4Z)-1-Methoxy-4-phenyl-2,4-undecadiene
(4c). Oil. 1H NMR
(400 MHz, CDCl3): d 7.35 (t, J ¼ 7.4 Hz, 2H), 7.27 (m, 1H), 7.12 (d, J ¼ 6.8 Hz, 2H),
6.45 (d, J ¼ 15.6 Hz, 1H), 5.72 (t, J ¼ 7.6 Hz, 1H), 5.21 (dt, J ¼ 15.6, 6.4 Hz, 1H),
3.91 (d, J ¼ 6.4 Hz, 2H), 3.30 (s, 3H), 1.94–1.88 (m, 2H), 1.34–1.16 (m, 8H), 0.84
(t, J ¼ 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3): d 140.32, 138.19, 137.09, 134.44,
129.49, 128.09, 126.75, 126.06, 73.10, 57.95, 31.66, 29.62, 29.06, 28.86, 22.60, 14.10;
IR (neat): n (cmꢂ1) 3058, 2927, 2854, 1729, 1595, 1493, 1449, 1122, 960, 703; MS
(EI, 70 eV): m=z 258 (Mþ, 1.5), 120 (35), 105 (100), 77 (57). Anal. calc. for
C18H26O: C, 83.67; H, 10.14. Found: C, 83.43; H, 9.97%.
1
(7Z,9E)-8-Tolyl-7,9-hexadecadiene (4d). Oil. H NMR (400 MHz, CDCl3):
d 7.16 (d, J ¼ 8.0 Hz, 2H), 6.97 (d, J ¼ 8.0 Hz, 2H), 6.20 (d, J ¼ 15.6 Hz, 1H), 5.51
(t, J ¼ 7.6 Hz, 1H), 5.06 (dt, J ¼ 15.6, 7.6 Hz, 1H), 2.35 (s, 3H), 2.02–1.97 (m, 2H),
1.90–1.84 (m, 2H), 1.35–1.15 (m, 16H), 0.90–0.85 (m, 6H); 13C NMR (100 MHz,
CDCl3): d 141.25, 139.38, 134.35, 132.19, 131.84, 130.23, 126.83, 125.19, 32.86,
31.74, 31.68, 29.85, 29.75, 29.36, 28.94, 28.89, 22.62, 21.56, 14.08, 14.04; IR (neat):
n (cmꢂ1) 3057, 2926, 2858, 1712, 1600, 1493, 1456, 1378, 961, 702; MS (EI, 70 eV):
m=z 312 (Mþ, 1.8), 91 (45), 57 (100). Anal. calc. for C23H36: C, 88.39; H, 11.61.
Found: C, 88.13; H, 11.84%.
(2E,4Z)-1-Methoxy-4-phenyl-2,4-nonadiene
(4e). Oil.
1H
NMR
(400 MHz, CDCl3): d 7.34–7.26 (m, 3H), 7.12–7.10 (m, 2H), 6.45 (d, J ¼ 15.6 Hz,
1H), 5.72 (t, J ¼ 7.2 Hz, 1H), 5.20 (dt, J ¼ 15.6, 6.0 Hz, 1H), 3.91 (d, J ¼ 6.0 Hz,
2H), 3.30 (s, 3H), 1.95–1.89 (m, 2H), 1.33–1.19 (m, 4H), 0.85 (t, J ¼ 7.2 Hz, 3H);
13C NMR (100 MHz, CDCl3): d 140.34, 138.18, 137.09, 134.39, 129.49, 128.10,
126.75, 126.08, 73.10, 57.93, 31.85, 28.80, 22.26, 13.95; IR (neat): n (cmꢂ1) 2957,
2926, 1597, 1464, 1379, 1122, 968, 703; MS (EI, 70 eV): m=z 230 (Mþ, 6), 105
(100), 77 (54), 57 (65). Anal. calc. for C16H22O: C, 83.43; H, 9.63. Found:
C, 83.20; H, 9.82%.
1
(1E,3Z)-1,3-Diphenyl-1,3-octadiene (4f). Oil. H NMR (400 MHz, CDCl3):
d 7.43–7.39 (m, 2H), 7.35–7.24 (m, 5H), 7.21–7.14 (m, 3H), 6.99 (d, J ¼ 16.0 Hz,
1H), 5.98 (d, J ¼ 16.0 Hz, 1H), 5.86 (t, J ¼ 7.6 Hz, 1H), 2.00–1.94 (m, 2H), 1.39–1.31
(m, 2H), 1.29–1.22 (m, 2H), 0.83 (t, J ¼ 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3):
d 141.24, 138.21, 137.71, 135.07, 133.36, 129.60, 129.05, 128.46, 128.14, 126.95,
126.83, 126.18, 31.90, 29.00, 22.27, 13.91; IR (neat): n (cmꢂ1) 3060, 3029, 2956,
2871, 1705, 1599, 1494, 1455, 1379, 965, 754, 700; MS (EI, 70 eV): m=z 262 (Mþ,
8.5), 105 (100), 77 (56), 57 (87). Anal. calc. for C20H22: C, 91.55; H, 8.45. Found:
C, 91.28; H, 8.67%.
1
(5Z,7E)-6-Phenyl-5,7-dodecadiene (4g). Oil. H NMR (400 MHz, CDCl3):
d 7.37–7.27 (m, 3H), 7.10 (d, J ¼ 7.6 Hz, 2H), 6.23 (d, J ¼ 15.6 Hz, 1H), 5.58
(t, J ¼ 7.6 Hz, 1H), 5.11 (dt, J ¼ 15.6, 7.6 Hz, 1H), 2.06–2.00 (m, 2H), 1.93–1.86
(m, 2H), 1.33–1.20 (m, 8H), 0.87–0.79 (m, 6H); 13C NMR (100 MHz, CDCl3): d
141.06, 138.97, 134.17, 131.60, 131.28, 129.54, 127.93, 126.48, 32.48, 32.05, 31.55,
28.65, 22.27, 22.26, 13.94, 13.92; IR (neat): n (cmꢂ1) 3058, 3023, 2958, 2872, 1723,