X. Li, G. Zou / Journal of Organometallic Chemistry 794 (2015) 136e145
143
d
(ppm): 7.84 (d, J ¼ 8.4 Hz, 2H), 7.30e7.17 (m, 7H), 3.25 (t,
133.2, 130.3, 130.2, 129.5, 128.5, 128.3, 125.2, 26.4, 16.0.
J ¼ 7.6 Hz, 2H), 3.04 (t, J ¼ 7.6 Hz, 2H), 2.38 (s, 3H); 13C NMR (CDCl3,
100 MHz)
128.2, 126.2, 40.4, 30.3, 21.7.
d (ppm): 198.9, 143.9, 141.5, 134.4, 129.3, 128.6, 128.5,
4.3.23. (2-Methoxyphenyl) (phenyl)methanone 3 cg [26]
Colorless oil, 1H NMR (CDCl3, 400 MHz)
d (ppm): 7.81 (d,
J ¼ 8.4 Hz, 2H), 7.57e7.53 (m, 1H), 7.49e7.41 (m, 3H), 7.36 (dd,
J ¼ 2.0, 7.6 Hz, 1H), 7.06e6.98 (m, 2H), 3.72 (s, 3H); 13C NMR (CDCl3,
4.3.14. 1-(p-Tolyl)octadecan-1-one 3pa
white solid, mp 64e65 ꢀC, 1H NMR (CDCl3, 400 MHz)
d (ppm):
100 MHz)
d (ppm): 196.5, 157.4, 137.8, 133.0, 132.0, 129.8, 129.6,
7.86 (d, J ¼ 8.4 Hz, 2H), 7.25 (d, J ¼ 8.4 Hz, 2H), 2.93 (t, J ¼ 7.4 Hz,
128.8, 128.3, 120.5, 111.5, 55.6.
2H), 2.41 (s, 3H), 1.75e1.68 (m, 2H), 1.33e1.25 (m, 28H), 0.88 (t,
J ¼ 6.8 Hz, 3H); 13C NMR (CDCl3, 100 MHz)
d (ppm): 200.2, 143.5,
134.6, 129.2, 128.2, 38.5, 32.0, 29.8, 29.71, 29.68, 29.57, 29.55, 29.45,
4.3.24. Phenyl(3-vinylphenyl)methanone 3ch [14a]
Light yellow oil, 1H NMR (CDCl3, 400 MHz)
d (ppm): 7.74e7.70
29.42, 24.5, 22.7, 21.6, 14.1. HRMS (ESI) m/z [Mþ1]þ calcd for
(m, 3H), 7.57e7.48 (m, 3H), 7.41e7.32 (m, 3H), 6.66 (dd, J ¼ 10.8,
17.6 Hz, 1H), 5.72 (d, J ¼ 17.6 Hz, 1H), 5.23 (d, J ¼ 10.8 Hz, 1H); 13C
C
25H43O 359.3314, found 359.3310.
NMR (CDCl3, 100 MHz)
d (ppm): 195.6, 136.8, 136.7, 136.4, 134.9,
4.3.15. Cyclohexyl(p-tolyl)methanone 3qa [21]
131.5, 129.0, 128.9, 128.4, 127.4, 127.3, 126.7, 114.3.
White solid, mp 62e63 ꢀC, 1H NMR (CDCl3, 400 MHz)
d (ppm):
7.85 (d, J ¼ 8.0 Hz, 2H), 7.25 (d, J ¼ 8.0 Hz, 2H), 3.27e3.20 (m, 1H),
4.3.25. 1-(o-Tolyl)octadecan-1-one 3pe [7]
2.40 (s, 3H), 1.89e1.82 (m, 4H), 1.54e1.25 (m, 6H); 13C NMR (CDCl3,
White solid, mp 44e45 ꢀC, 1H NMR (CDCl3, 400 MHz)
d (ppm):
100 MHz)
25.9, 21.6.
d (ppm): 203.5, 143.4, 133.8, 129.3, 128.4, 45.5, 29.5, 26.0,
7.60 (d, J ¼ 7.6 Hz, 1H), 7.37e7.33 (m, 1H), 7.24 (t, J ¼ 7.6 Hz, 2H),
2.87 (t, J ¼ 7.6 Hz, 2H), 2.48 (s, 3H), 1.73e1.65 (m, 2H), 1.36e1.25 (m,
28H), 0.88 (t, J ¼ 7.2 Hz, 3H); 13C NMR (CDCl3, 100 MHz)
d (ppm):
4.3.16. o-Tolyl(p-tolyl)methanone 3ra [19]
204.9, 138.4, 137.8, 131.9, 131.0, 128.3, 125.6, 41.7, 32.0, 29.73, 29.70,
29.6, 29.54, 29.51, 29.40, 29.37, 24.5, 22.7, 21.2, 14.1.
Light yellow oil, 1H NMR (CDCl3, 400 MHz)
d (ppm): 7.71 (d,
J ¼ 8.4 Hz, 2H), 7.40e7.36 (m, 1H), 7.30e7.22 (m, 5H), 2.42 (s, 3H),
2.31 (s, 3H); 13C NMR (CDCl3, 100 MHz)
d
(ppm): 198.4, 144.1, 139.0,
4.3.26. 1-(2-Ethylphenyl)octadecan-1-one 3pf [7]
136.5, 135.2, 130.9, 130.3, 130.1, 129.2, 128.3, 125.2, 21.7, 19.9.
White solid, mp 47e49 ꢀC, 1H NMR (CDCl3, 400 MHz)
d (ppm):
7.53 (dd, J ¼ 7.6, 1.2 Hz, 1H), 7.39e7.35 (m, 1H), 7.27e7.21 (m, 2H),
2.86 (t, J ¼ 7.2 Hz, 2H), 2.80 (q, J ¼ 7.2 Hz, 2H), 1.73e1.66 (m, 2H),
1.30e1.20 (m, 31H), 0.88 (t, J ¼ 7.2 Hz, 3H); 13C NMR (CDCl3,
4.3.17. (3r,5r,7r)-Adamantan-1-yl(p-tolyl)methanone 3sa [25]
Light yellow solid, mp 65e66 ꢀC, 1H NMR (CDCl3, 400 MHz)
d
(ppm): 7.53 (d, J ¼ 8.0 Hz, 2H), 7.19 (d, J ¼ 8.0 Hz, 2H), 2.37 (s, 3H),
2.07e2.02 (m, 9H), 1.78e1.71 (m, 6H); 13C NMR (CDCl3, 100 MHz)
(ppm): 209.3, 140.7, 136.5, 128.6, 127.6, 46.9, 39.3, 36.6, 28.2, 21.4.
100 MHz)
d (ppm): 205.4, 143.6, 138.7, 130.9, 130.3, 127.9, 125.5,
42.2, 32.0, 29.74, 29.70, 29.66, 29.5, 29.41, 29.36, 26.9, 24.4, 22.7,
16.1, 14.1.
d
4.3.18. (4-Fluorophenyl) (phenyl)methanone 3 cb [7]
Light yellow oil, 1H NMR (CDCl3, 400 MHz)
(ppm): 7.86e7.83
(m, 2H), 7.78e7.76 (m, 2H), 7.61e7.57 (m, 1H), 7.50e7.47 (m, 2H),
7.18e7.13 (m, 2H); 13C NMR (CDCl3, 100 MHz)
(ppm): 195.2, 165.4
4.3.27. 1-(2-Methoxyphenyl)octadecan-1-one 3 pg
d
White solid, mp 42e43 ꢀC, 1H NMR (CDCl3, 400 MHz)
d (ppm):
7.64 (dd, J ¼ 1.6, 7.6 Hz, 1H), 7.44e7.39 (m, 1H), 6.99e6.92 (m, 2H),
d
3.87 (s, 3H), 2.95 (t, J ¼ 7.6 Hz, 2H), 1.70e1.63 (m, 2H), 1.31e1.25 (m,
(d, J ¼ 252.4 Hz), 137.5, 133.8 (d, J ¼ 2.9 Hz), 132.7, 132.6 (d,
28H), 0.88 (t, J ¼ 7.2 Hz, 3H); 13C NMR (CDCl3, 100 MHz)
d (ppm):
J ¼ 14.5 Hz), 129.9, 128.4, 115.5 (d, J ¼ 21.7 Hz).
203.2, 158.3, 133.0, 130.1, 128.8, 120.6, 111.4, 55.4, 43.8, 32.0, 29.74,
29.71, 29.69, 29.58, 29.56, 29.45, 29.41, 24.4, 22.7, 14.1. HRMS (ESI)
m/z [Mþ1]þ calcd for C25H43O2 375.3258, found 375.3254.
4.3.19. (4-Methoxyphenyl) (phenyl)methanone 3cc [7]
White solid, mp 59e60 ꢀC, 1H NMR (CDCl3, 400 MHz)
d (ppm):
7.84e7.81 (m, 2H), 7.76e7.74 (m, 2H), 7.56 (t, J ¼ 7.2 Hz, 1H), 7.46 (t,
J ¼ 7.6 Hz, 2H), 6.98e6.95 (m, 2H), 3.87 (s, 3H); 13C NMR (CDCl3,
4.3.28. Cyclohexyl(o-tolyl)methanone 3qe [7]
Colorless oil, 1H NMR (CDCl3, 400 MHz)
d (ppm): 7.42e7.40 (m,
100 MHz)
d (ppm): 195.6, 163.2, 138.3, 132.6, 131.9, 130.1, 129.7,
1H), 7.27e7.23 (m, 1H), 7.19e7.14 (m, 2H), 2.99e2.92 (m, 1H), 2.33
128.2, 113.6, 55.5.
(s, 3H), 1.80e1.71 (m, 5H), 1.38e1.17 (m, 5H); 13C NMR (CDCl3,
100 MHz)
49.0, 28.8, 26.0, 25.8, 20.6.
d (ppm): 208.8, 138.9, 137.2, 131.5, 130.4, 127.3, 125.5,
4.3.20. Benzophenone 3cd [7]
Light yellow solid, mp 46e47 ꢀC, 1H NMR (CDCl3, 400 MHz)
d
(ppm): 7.71e7.69 (m, 4H), 7.48 (t, J ¼ 7.6 Hz, 2H), 7.37 (t, J ¼ 8.0 Hz,
4H); 13C NMR (CDCl3, 100 MHz)
128.3.
d (ppm): 196.8, 137.6, 132.5, 130.1,
4.3.29. Cyclohexyl(2-ethylphenyl)methanone 3qf
Colorless oil, 1H NMR (CDCl3, 400 MHz)
d
(ppm):7.44 (dd, J ¼ 0.8,
7.6 Hz, 1H), 7.39e7.34 (m, 1H), 7.28e7.21 (m, 2H), 3.04e2.97 (m,
1H), 2.72 (q, J ¼ 7.6 Hz, 2H), 1.89e1.68 (m, 5H), 1.48e1.27 (m, 5H),
4.3.21. Phenyl(o-tolyl)methanone 3ce [7]
1.22 (t, J ¼ 7.6 Hz, 3H); 13C NMR (CDCl3, 100 MHz)
d (ppm): 209.2,
Light yellow oil, 1H NMR (CDCl3, 400 MHz)
d (ppm): 7.73e7.71
143.3, 139.0, 130.5, 130.0, 127.1, 125.4, 49.3, 28.9, 26.7, 26.0, 25.8,
16.2. HRMS (ESI) m/z [Mþ1]þ calcd for C15H21O 217.1587, found
217.1586.
(m, 2H), 7.50 (t, J ¼ 7.2 Hz, 1H), 7.37 (t, J ¼ 7.6 Hz, 2H), 7.33e7.29 (m,
1H), 7.24e7.15 (m, 3H), 2.25 (s, 3H); 13C NMR (CDCl3, 100 MHz)
d
(ppm): 198.7, 138.6, 137.7, 136.8, 133.2, 131.0, 130.3, 130.2, 128.53,
128.48, 125.2, 20.0.
4.3.30. Cyclohexyl(2-methoxyphenyl)methanone 3qg [27]
4.3.22. (2-Ethylphenyl) (phenyl)methanone 3cf [7]
Colorless oil, 1H NMR (CDCl3, 400 MHz)
d
(ppm): 7.48 (dd, J ¼ 1.6,
Light yellow oil, 1H NMR (CDCl3, 400 MHz)
d
(ppm): 7.82e7.80
7.2 Hz, 1H), 7.42e7.38 (m, 1H), 6.99e6.92 (m, 2H), 3.86 (s, 3H),
(m, 2H), 7.59e7.54 (m, 1H), 7.46e7.40 (m, 3H), 7.34 (d, J ¼ 7.2 Hz,
3.22e3.15 (m, 1H), 1.91e1.66 (m, 5H), 1.41e1.24 (m, 5H); 13C NMR
1H), 7.28e7.22 (m, 2H), 2.67 (q, J ¼ 7.6 Hz, 2H), 1.16 (t, J ¼ 7.6 Hz,
(CDCl3, 100 MHz)
d (ppm): 207.3, 157.6, 132.5, 129.8, 120.6, 111.4,
3H); 13C NMR (CDCl3, 100 MHz)
d (ppm): 198.8, 143.0, 138.4, 137.8,
55.6, 50.1, 28.8, 26.1, 26.0.