F. Zhang et al.
Cyclopentyl(2-cyclopentylphenyl)methanone (3g)
Cyclopent
Cyclopent
4-Methyl-biphenyl-2-yl)-(4-methyl-phenyl)-methanone(3k)
Me
O
O
A colorless liquid. IR:(KBr) vmax 2953, 2867, 1807, 1765, 1687,
1464, 1371, 1119, 1071, 758 cm−1 1H NMR: (600 MHz, CDCl3) δ
Me
;
7.39–7.35 (m, 3H, CH arom), 7.21–7.19 (m, 1H, CH arom), 3.47 (tt,
A white solid. M.p. = 152–153 ◦C IR:(KBr) vmax 3030, 2963, 1659,
1600, 1512, 1474, 1379, 1253, 1150, 1044, 923, 823, 775 cm−1; 1H
NMR: (600 MHz, CDCl3) δ 7.60 (d, J = 7.8 Hz, 2H, CH arom), 7.53
(t, J = 7.8 Hz, 2H, CH arom), 7.47–7.40 (m, 3H, CH arom), 7.16 (d,
J = 7.8 Hz, 1H, CH arom), 7.10 (d, J = 7.8 Hz, 2H, CH arom), 7.02
J = 15.6 Hz, 7.8 Hz, 1H, CH to C O), 3.20 (tt, J = 17.4 Hz, 8.4 Hz,
1H, PhCH), 1.86–1.62 (m, 8H, 4CH2), 1.58–1.25 (m, 8H, 4CH2); 13
C
NMR: (150 MHz, CDCl3) δ 208.83 (C O), 144.11 (C arom), 140.02 (C
arom), 129.34 (C arom), 126.05 (C arom), 125.53 (C arom), 124.30 (C
arom), 50.12 (CH to C O), 40.91 (PhCH), 34.71 (CH2), 28.81 (CH2),
(d, J = 7.8 Hz, 2H, CH arom), 2.34 (s, 3H, CH3), 2.25 (s, 3H, CH3); 13
C
26.52 (CH2), 25.20 (CH2), 25.08 (CH2); HRMS calcd for C17H22
O
NMR: (150 MHz, CDCl3) δ 198.51 (C O), 143.82 (C arom), 141.02 (C
arom), 139.12 (C arom), 137.37 (C arom), 137.03 (C arom), 134.88 (C
arom), 130.27 (C arom), 130.17 (C arom), 130.12 (C arom), 129.07 (C
arom), 128.94 (C arom), 128.81 (C arom), 128.56 (C arom), 126.69 (C
arom), 22.25 (CH3), 21.72 (CH3); HRMS calcd for C21H18O 286.1358;
found: 286.1366.
242.1671; found: 242.1678.
1-(2-Heptylphenyl)octan-1-one (3h)
O
n-Hept
n-Hept
4-Methoxy-biphenyl-2-yl)-(4-methoxy-phenyl)-methanone(3l)
OMe
A colorless liquid. IR:(KBr) vmax 2924, 2858, 1689, 1457, 1372, 1220,
653 cm−1; 1H NMR: (600 MHz, CDCl3) δ 7.52 (d, J = 7.8 Hz, 1H, CH
arom), 7.37–7.35 (m, 1H, CH arom), 7.26–7.22 (m, 2H, CH arom),
2.86 (t, J = 7.8 Hz, 2H, CH2 to C O), 2.76 (t, J = 7.8 Hz, 2H, PhCH2),
1.72–1.67 (m, 2H, CH2), 1.61–1.53 (m, 2H, CH2), 1.35–1.26 (m,
16H, 8CH2), 0.89–0.86 (m, 6H, 2CH3); 13C NMR: (150 MHz, CDCl3) δ
205.73 (C O), 142.29 (C arom), 139.10 (C arom), 130.94 (C arom),
130.73 (C arom), 127.90 (C arom), 125.58 (C arom), 42.38 (CH2
to C O), 33.84 (PhCH2), 32.07 (CH2), 31.93 (CH2), 31.81 (CH2),
29.78 (CH2), 29.40 (CH2), 29.28 (CH2), 29.23 (CH2), 24.51 (CH2),
22.75 (CH2), 22. 71 (CH2), 14.18 (CH3), 14.15 (CH3); HRMS calcd for
C21H34O 302.2610; found: 302.2606.
O
OMe
A white solid. M.p. = 101–102 ◦C IR:(KBr) vmax 2933, 2839, 1644,
1601, 1511, 1450, 1301, 1251, 1144, 1023, 926, 841, 765 cm−1; 1H
NMR: (600 MHz, CDCl3) δ 7.60 (d, J = 8.4 Hz, 2H, CH arom), 7.53
(t, J = 7.2 Hz, 2H, CH arom), 7.46–7.39 (m, 3H, CH arom), 7.24 (d,
J = 8.4 Hz, 1H, CH arom), 6.76 (t, J = 8.4 Hz, 4H, CH arom), 3.80 (s,
3H, OCH3), 3.73 (s, 3H, OCH3); 13C NMR: (150 MHz, CDCl3) δ 197.66
(C O), 163.38 (C arom), 158.92 (C arom), 140.33 (C arom), 139.18
(C arom), 132.76 (C arom), 132.39 (C arom), 130.34 (C arom), 130.05
(C arom), 129.99 (C arom), 129.95 (C arom), 128.42 (C arom), 126.62
(C arom), 113.79 (C arom), 113.45 (C arom), 55.44 (OCH3), 55.20
(OCH3); HRMS calcd for C21H18O3 318.1256; found: 318.1259.
1-(2-Octylphenyl)nonan-1-one (3i)
O
n-Oct
n-Oct
4-Dimethylamino-biphenyl-2-yl)-(4-dimethylamino-phenyl)-
methanone (3m)
A colorless liquid. IR:(KBr) vmax 2953, 2929, 2857, 1690, 1467, 1366,
752 cm−1; 1H NMR: (600 MHz, CDCl3) δ 7.52 (d, J = 7.8 Hz, 1H, CH
arom), 7.37–7.35 (m, 1H, CH arom), 7.26–7.22 (m, 2H, CH arom),
2.86 (t, J = 7.2 Hz, 2H, CH2 to C O), 2.76 (t, J = 7.8 Hz, 2H,
PhCH2), 1.71–1.68 (m, 2H,CH2), 1.56–1.54 (m, 2H,CH2), 1.34–1.22
(m, 20H, 10CH2), 0.88 (m, 6H, 2CH3); 13C NMR: (150 MHz, CDCl3)
δ 205.59 (C O), 142.28 (C arom), 139.11 (C arom), 130.92 (C
arom), 130.69 (C arom), 127.88 (C arom), 125.55 (C arom), 42.35
(CH2 to C O), 33.83 (PhCH2), 32.04 (CH2), 31.97 (CH2), 31.92
(CH2), 29.82 (CH2), 29.56 (CH2), 29.52 (CH2), 29.43 (CH2), 29.35
(CH2), 29.25 (CH2), 24.50 (CH2), 22.74 (CH2), 22.72 (CH2), 14.18
(CH3), 14.14 (CH3); HRMS calcd for C23H38O 330.2923; found:
330.2917.
NMe2
O
NMe2
A green solid. M.p. = 171–173 ◦C IR:(KBr) vmax 3898, 1593, 1531,
1478, 1441, 1370, 1291, 1190, 1142, 1062, 934, 817, 762 cm−1
;
1H NMR: (600 MHz, CDCl3) δ 7.68 (d, J = 9.0 Hz, 2H, CH arom),
7.50–7.46 (m, 3H), 7.39–7.33 (m, 2H, CH arom), 7.25 (d, J = 8.4 Hz,
1H, CH arom), 6.62 (d, J = 9.0 Hz, 2H, CH arom), 6.54 (d, J = 9.0 Hz,
2H, CH arom), 3.02 [s, 6H, N(CH3)2], 2.90 [s, 6H, N(CH3)2]; 13C NMR:
(150 MHz, CDCl3)δ 197.32(C O), 153.28(Carom), 149.61(Carom),
140.53 (C arom), 139.68 (C arom), 132.52 (C arom), 129.75 (C arom),
Biphenyl-2-yl-phenyl-methanone (3j)[41]
A white solid. The spectra data is identical to the literature.
c
Copyright ꢀ 2009 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2010, 24, 57–63