X.-Y. Tang, M. Shi / Tetrahedron 65 (2009) 8863–8868
8867
1638, 1465, 1378, 1149, 1092, 1053 cmꢁ1; MS (EI) m/z (%): 180 [Mþ]
(0.8), 109 (18.2), 96 (11.4), 95 (100.0), 82 (47.2), 81 (32.9), 67 (22.3),
55 (15.9); HRMS (EI) calcd for C12H20O (Mþ) requires 180.1514,
found: 180.1515.
(13.4); HRMS (EI) calcd for C18H15OCl (Mþ) requires 282.0811,
found: 282.0810.
3.2.15. (2E,4E)-1,5-Diphenylpenta-2,4-dien-1-one 2f. A known com-
pound.11 1H NMR (CDCl3, 300 MHz, TMS)
d 7.02–7.04 (m, 2H), 7.10 (d,
3.2.9. (E)-1-(2-Benzylidenecyclopropyl)but-3-en-1-one 1j. A white
J¼15.0 Hz, 1H), 7.32–7.41 (m, 4H, Ar), 7.46–7.62 (m, 5H), 7.97–7.99
solid. Mp 65–67 ꢀC. 1H NMR (CDCl3, 400 MHz, TMS)
d
1.98–2.05 (m,
(m, 2H, Ar).
1H), 2.16–2.20 (m, 1H), 2.65–2.68 (m, 1H), 3.20–3.23 (m, 1H), 5.14–
5.30 (m, 2H), 5.90–5.99 (m, 1H), 6.75–6.77 (m, 1H), 7.24–7.34 (m,
1H, Ar), 7.35–7.37 (m, 2H, Ar), 7.52 (d, J¼8.0 Hz, 2H, Ar); 13C NMR
3.2.16. (2E,4E)-5-Phenylpenta-2,4-dienal 2g. A known compound.12
1H NMR (CDCl3, 300 MHz, TMS)
d 6.24–6.31 (m, 1H), 7.00–7.02 (m,
(CDCl3, 100 MHz, TMS)
d
13.4, 24.2, 45.6, 118.9, 119.5, 124.3, 127.1,
2H), 7.23–7.42 (m, 4H), 7.50–7.52 (m, 2H, Ar), 9.61 (d, J¼6.6 Hz, 1H,
127.6, 128.6, 130.5, 136.5, 205.5; IR (CH2Cl2):
n
3062, 3029, 2926,
CHO); 13C NMR (CDCl3, 75 MHz, TMS)
131.5, 135.5, 142.5, 152.2, 193.7.
d 126.1, 127.5, 128.9, 129.7,
1785, 1711, 1638, 1496, 1452, 1421, 1390 cmꢁ1; MS (EI) m/z (%): 198
[Mþ] (17.9), 157 (99.8), 156 (19.4), 149 (16.5), 129 (99.5), 128 (100.0),
127 (45.1), 41 (16.1); HRMS (EI) calcd for C14H14O (Mþ) requires
198.1045, found: 198.1043.
3.2.17. (3E,5E)-6-Phenylhexa-3,5-dien-2-one 2h. A known com-
pound.13 1H NMR (CDCl3, 400 MHz, TMS)
2.31 (s, 3H, CH3), 6.26
d
(d, J¼15.2 Hz, 1H), 6.85–6.97 (m, 2H), 7.26–7.38 (m, 4H), 7.46–7.48
3.2.10. (E)-1-(2-Benzylidenecyclopropyl)pent-4-en-1-one 1k. A col-
(m, 2H, Ar); 13C NMR (CDCl3, 100 MHz, TMS)
129.7, 131.5, 135.5, 142.5, 152.2, 193.7.
d 126.1, 127.5, 128.9,
orless oil. 1H NMR (CDCl3, 400 MHz, TMS)
d 1.95–2.00 (m, 1H), 2.13–
2.19 (m, 1H), 2.34–2.39 (m, 2H), 2.51–2.57 (m, 2H), 2.61–2.64 (m,
1H), 4.97–5.07 (m, 2H), 5.76–5.86 (m, 1H), 6.75–6.76 (m, 1H), 7.23–
7.28 (m, 1H, Ar), 7.32–7.37 (m, 2H, Ar), 7.51 (m, 2H, Ar); 13C NMR
3.2.18. (2E,4E)-Dodeca-2,4-dienal 2i. A colorless oil. 1H NMR (CDCl3,
400 MHz, TMS) 0.87–0.90 (m, 3H), 1.25–1.33 (m, 8H), 1.42–1.48 (m,
d
(CDCl3, 100 MHz, TMS)
d
13.2, 24.5, 27.9, 39.6, 115.3, 119.3, 124.3,
2H), 2.19–2.25 (m, 2H), 6.08 (dd, J¼15.2, 7.6 Hz, 1H), 6.24–6.36 (m,
127.1, 127.6, 128.5, 136.5, 137.0, 207.1; IR (CH2Cl2):
n 3085, 3062,
2H), 7.05–7.12 (m, 2H), 9.54 (d, J¼7.6 Hz, 1H); 13C NMR (CDCl3,
3029, 2969, 1785, 1703, 1592, 1491, 1454, 1414, 1363 cmꢁ1; MS (EI)
100 MHz, TMS) d 14.1, 22.6, 28.5, 29.0, 29.1, 31.7, 33.2, 128.6, 130.0,
m/z (%): 212 [Mþ] (27.8), 171 (47.5), 157 (42.9), 129 (88.8), 128
147.5, 152.9, 194.0; IR (CH2Cl2): n 2957, 2927, 2856, 2714, 1715, 1686,
(100.0),127 (33.1),115 (26.8), 55 (33.2); HRMS (EI) calcd for C15H16
O
1640, 1465, 1378, 1050, 1115 cmꢁ1; MS (EI) m/z (%): 180 [Mþ] (1.9),
109 (18.7), 95 (100.0), 82 (46.0), 81 (46.4), 67 (24.2), 55 (18.6), 41
(26.8); HRMS (EI) calcd for C12H20O (Mþ) requires 180.1514, found:
180.1516.
(Mþ) requires 212.1201, found: 212.1203.
3.2.11. (3E,5E)-1,6-Diphenylhexa-3,5-dien-2-one 2a. A known com-
pound.10 1H NMR (CDCl3, 300 MHz, TMS)
d 3.85 (s, 2H, CH2), 6.31 (d,
J¼15.6 Hz, 1H), 6.77–6.95 (m, 2H), 7.23–7.44 (m, 11H); 13C NMR
3.2.19. (2E,5E,7E)-8-Phenylocta-2,5,7-trien-4-one 2j. A white solid.
(CDCl3, 75 MHz, TMS)
d
48.3, 126.5, 126.9, 127.2, 128.4, 128.7, 128.8,
Mp 112–114 ꢀC. 1H NMR (CDCl3, 400 MHz, TMS)
d
1.95 (dd, J¼6.8,
129.2, 129.4, 134.5, 135.9, 141.7, 143.3, 197.3.
1.6 Hz, 3H, CH3), 6.41 (dq, J¼15.2,1.6 Hz,1H), 6.51 (d, J¼15.2 Hz,1H),
6.89–7.01 (m, 3H), 7.30–7.49 (m, 6H); 13C NMR (CDCl3, 100 MHz,
3.2.12. (3E,5E)-1-Phenyl-6-(3,4,5-trimethoxyphenyl)hexa-3,5-dien-
TMS)
d 18.5,126.9,127.2, 128.3, 128.8, 129.1,130.8, 136.1,141.2, 143.0,
2-one 2b. A white solid. Mp 90–92 ꢀC. 1H NMR (CDCl3, 400 MHz,
143.1, 189.2; IR (CH2Cl2): n 3028, 2925, 2852, 1660, 1627, 1582, 1494,
TMS)
J¼15.2 Hz, 1H), 6.67 (s, 2H, Ar), 6.71–6.87 (m, 2H), 7.24–7.28 (m,
3H), 7.32–7.42 (m, 3H); 13C NMR (CDCl3,100 MHz, TMS)
48.4, 56.0,
60.8, 104.2, 125.9, 126.8, 128.0, 128.6, 129.4, 131.5, 134.5, 139.1, 141.6,
d
3.85 (s, 2H, CH2), 3.86 (s, 3H, CH3), 3.87 (s, 6H, 2CH3), 6.32 (d,
1447,1350,1293 cmꢁ1; MS (EI) m/z (%): 198 [Mþ] (100.0),197 (29.9),
155 (26.9), 129 (34.4), 128 (59.2), 127 (22.2), 121 (20.9), 91 (18.8);
HRMS (EI) calcd for C14H14O (Mþ) requires 198.1045, found:
198.1049.
d
143.2,153.3,197.2; IR (CH2Cl2): n 3061, 2998, 2939, 2838,1784,1703,
1584, 1505, 1462, 1424 cmꢁ1; MS (EI) m/z (%): 338 [Mþ] (27.5), 248
(15.7), 247 (100.0), 219 (12.4), 216 (18.7), 188 (13.1), 115 (8.2), 91
(24.0); HRMS (EI) calcd for C21H22O4 (Mþ) requires 338.1518, found:
338.1528.
3.2.20. (1E,3E)-1-Phenylnona-1,3,8-trien-5-one 2k. A colorless oil.
1H NMR (CDCl3, 400 MHz, TMS)
d 2.38–2.44 (m, 2H, CH2), 2.68–2.72
(m, 2H, CH2), 4.99–5.09 (m, 2H), 5.81–5.91 (m, 1H), 6.29 (d,
J¼15.2 Hz, 1H), 6.84–6.97 (m, 2H), 7.29–7.38 (m, 4H), 7.46–7.48 (m,
2H, Ar); 13C NMR (CDCl3, 100 MHz, TMS)
d 28.2, 39.7, 115.2, 126.6,
3.2.13. (3E,5E)-6-(4-Bromophenyl)-1-phenylhexa-3,5-dien-2-one
127.2, 128.8, 129.1, 129.5, 136.0, 137.2, 141.3, 142.5, 199.6; IR
2c. A yellow solid. Mp 92–94 ꢀC. 1H NMR (CDCl3, 400 MHz, TMS)
(CH2Cl2): n 3079, 3028, 3002, 2919, 1785, 1681, 1588, 1495, 1449,
d
3.86 (s, 2H, CH2), 6.32 (d, J¼15.2 Hz, 1H), 6.76–6.87 (m, 2H), 7.23–
7.42 (m, 8H), 7.44–7.47 (m, 2H, Ar); 13C NMR (CDCl3, 100 MHz, TMS)
48.4, 123.2, 126.9, 127.2, 128.5, 128.7, 128.8, 129.4, 131.9, 134.4,
1406, 1362 cmꢁ1; MS (EI) m/z (%): 212 [Mþ] (24.5), 171 (22.1), 157
(100.0), 131 (23.0), 130 (34.7), 129 (52.4), 128 (76.2), 127 (27.6);
HRMS (EI) calcd for C15H16O (Mþ) requires 212.1201, found:
212.1199.
d
134.8, 140.1, 142.8, 197.2; IR (CH2Cl2): n 3028, 2891, 1763, 1736, 1718,
1683, 1612, 1594, 1580, 1487 cmꢁ1; MS (EI) m/z (%): 326 [Mþ] (4.0),
238 (12.3), 237 (97.3), 235 (100.0), 156 (23.4), 128 (76.4), 127 (18.5),
102 (9.2); HRMS (EI) calcd for C18H15OBr (Mþ) requires 326.0306,
found: 326.0305.
3.2.21. 1,6-Diphenylhexane-1,5-dione 3a. A known compound.14 1H
NMR (CDCl3, 300 MHz, TMS)
d 1.95–2.04 (m, 2H, CH2), 2.60 (t,
J¼7.2 Hz, 2H, CH2), 2.95 (t, J¼7.2 Hz, 2H, CH2), 3.70 (s, 2H, CH2),
7.19–7.34 (m, 5H, Ar), 7.42–7.47 (m, 2H, Ar), 7.53–7.58 (m, 1H, Ar),
7.92 (dd, J¼7.2, 1.5 Hz, 2H, Ar); 13C NMR (CDCl3, 100 MHz, TMS)
3.2.14. (3E,5E)-6-(4-Chlorophenyl)-1-phenylhexa-3,5-dien-2-one
2d. A yellow solid. Mp 88–90 ꢀC. 1H NMR (CDCl3, 400 MHz, TMS)
d 18.1, 37.3, 40.8, 50.2, 127.0, 128.0, 128.5, 128.7, 129.4, 133.0, 134.1,
d
3.85 (s, 2H, CH2), 6.30 (d, J¼15.2 Hz, 1H), 6.74–6.88 (m, 2H), 7.23–
7.39 (m, 10H); 13C NMR (CDCl3, 100 MHz, TMS)
48.4, 126.9, 127.1,
128.3, 128.7, 128.8, 129.0, 129.4, 134.3, 134.4, 134.8, 140.1, 142.8,
136.7, 199.7, 208.0.
d
3.2.22. 6-Phenyl-1-(3,4,5-trimethoxyphenyl)hexane-1,5-dione 3b. A
197.2; IR (CH2Cl2):
n
3086, 3062, 3028, 2924, 1683, 1615, 1597, 1583,
yellow oil. 1H NMR (CDCl3, 400 MHz, TMS)
d 1.95–2.02 (m, 2H, CH2),
1491, 1453, 1406, 1344 cmꢁ1; MS (EI) m/z (%): 282 [Mþ] (8.1), 193
2.60 (t, J¼7.2 Hz, 2H, CH2), 2.91 (t, J¼7.2 Hz, 2H, CH2), 3.70 (s, 2H,
(32.2), 192 (13.2), 191 (100.0), 156 (7.4), 128 (38.0), 127 (24.8), 91
CH2), 3.91 (s, 9H, 3CH3), 7.19–7.21 (m, 4H, Ar), 7.24–7.27 (m, 1H, Ar),