Vol. 66, No. 9 (2018)
Chem. Pharm. Bull.
877
2
Diethyl (2-Oxo-2-(3,4,5-trimethoxyphenyl)ethyl)phosphonate (3f)
7.16–7.12 (m, 2H), 4.17–4.09 (m, 4H), 3.59 (d, JP–H=22.8Hz,
2H), 1.28 (td, 3J=7.2, JP–H=0.4Hz, 6H); 13C-NMR
4
2
(100MHz, CDCl3) δ: 190.32 (d, JP–C=6.4Hz), 166.09 (d,
1JF-C=255.1Hz), 132.95–132.93 (m), 131.85 (d, JF-C=9.5Hz),
3
2
2
115.73 (d, JF-C=21.9Hz), 62.69 (d, JP–C=6.6Hz), 38.63 (d,
1JP–C=128.7Hz), 16.23 (d, JP–C=6.4Hz); IR (neat): 2985,
3
2934, 1681, 1598, 1508, 1414, 1249, 1160, 1026, 970, 823cm−1;
HR-MS (ESI, TFA-Na): Calcd for C12H16FNaO4P [M+Na]+
Yellow oil; 1H-NMR (400MHz, CDCl3) δ: 7.32 (s, 2H), 297.0668, found 297.0657.
2
4.18–4.11 (m, 4H), 3.92 (s, 9H), 3.60 (d, JP–H=22.8Hz, 2H),
Diethyl (2-(4-Chlorophenyl)-2-oxoethyl)phosphonate (3j)46)
1.30 (t, J=7.2Hz, 6H); 13C-NMR (100MHz, CDCl3) δ: 190.64
2
3
(d, JP–C=6.4Hz), 152.97, 143.11, 131.66 (d, JP–C=1.6Hz),
2
106.68, 62.68 (d, JP–C=6.4Hz), 60.93, 56.30, 38.73 (d,
1JP–C=128.6Hz), 16.27 (d, JP–C=6.2Hz); IR (neat) 2982, 2935,
3
2836, 1675, 1585, 1505, 1462, 1417, 1335, 1253, 1128, 1024,
969, 895cm−1; HR-MS (ESI, TFA-Na): Calcd for C15H23NaO7P
[M+Na]+ 369.1079, found 369.1070.
Yellow oil; 1H-NMR (400MHz, CDCl3) δ: 7.95 (d,
Diethyl (2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoethyl)phospho- J=8.4Hz, 2H), 7.44 (d, J=8.4Hz, 2H), 4.16−4.08 (m, 4H),
2
nate (3g)45)
3.58 (d, JP–H=22.8Hz, 2H), 1.27 (t, J=7.2Hz, 6H); 13C-NMR
2
(100MHz, CDCl3) δ: 190.68 (d, JP–C=6.4Hz), 140.22, 134.78
(d, JP–C=1.9Hz), 130.46, 128.88, 62.70 (d, JP–C=6.5Hz),
3
2
1
3
38.62 (d, JP–C=128.7Hz), 16.20 (d, JP–C=6.4Hz); IR
(neat): 2987, 2939, 1689, 1412, 1328, 1254, 1170, 1131, 1066,
1026, 970, 822cm−1; HR-MS (ESI, TFA-Na): Calcd for
C12H16ClNaO4P [M+Na]+ 313.0372, found 313.0357.
1
Yellow oil; H-NMR (400MHz, CDCl3) δ: 7.64 (dd, J=8.0,
Diethyl (2-Oxo-2-(4-(trifluoromethyl)phenyl)ethyl)phospho-
1.6Hz, 1H), 7.48 (d, J=1.6Hz, 1H), 6.87 (d, J=8.0Hz, 1H), nate (3k)45)
2
6.05 (s, 2H), 4.18–4.10 (m, 4H), 3.55 (d, JP–H=22.4Hz, 2H),
1.30 (t, J=7.2Hz, 6H); 13C-NMR (100MHz, CDCl3) δ: 189.84
2
3
(d, JP–C=6.4Hz), 152.35, 148.26, 131.45 (d, JP–C=1.8Hz),
2
126.06, 108.51, 107.85, 101.99, 62.63 (d, JP–C=6.6Hz), 38.45
1
3
(d, JP–C=129.4Hz), 16.28 (d, JP–C=6.2Hz); IR (neat): 2984,
2905, 1671, 1604, 1490, 1446, 1353, 1262, 1034, 969, 809cm−1;
HR-MS (ESI, TFA-Na): Calcd for C13H17NaO6P [M+Na]+
323.0660, found 323.0656.
Yellow oil; 1H-NMR (400MHz, CDCl3) δ: 8.13 (d,
J=8.4Hz, 2H), 7.74 (d, J=8.4Hz, 2H), 4.18−4.10 (m,
Diethyl (2-(Naphthalen-2-yl)-2-oxoethyl)phosphonate (3h)46) 4H), 3.64 (d, JP–H=23.2Hz, 2H), 1.28 (t, J=7.2Hz, 6H);
2
13C-NMR (100MHz, CDCl3) δ: 191.07 (d, JP–C=6.7Hz),
2
3
139.08, 135.00–134.34 (m), 129.39, 125.65 (q, JF-C=3.6Hz),
1
2
123.48 (q, JF-C=271.5Hz), 62.80 (d, JP–C=6.4Hz), 38.95 (d,
1JP–C=128.6Hz), 16.21 (d, JP–C=6.2Hz); IR (neat): 2984, 2937,
3
1681, 1589, 1402, 1253, 1092, 1025, 969, 814cm−1; HR-MS
(ESI, TFA-Na): Calcd for C13H16F3NaO4P [M+Na]+ 347.0636,
1
Yellow oil; H-NMR (400MHz, CDCl3) δ: 8.56–8.56 (brs, found 347.0631.
1H), 8.06 (dd, J=8.0, 2.0Hz, 1H), 7.99 (d, J=8.0Hz, 1H),
7.91−7.87 (m, 2H), 7.64−7.60 (m, 1H), 7.59–7.55 (m, 1H),
Diethyl (1-Oxo-1-phenylpropan-2-yl)phosphonate (3l)38)
2
4.20−4.11 (m, 4H), 3.76 (d, JP–H=22.8Hz, 2H), 1.28 (td,
4
3J=7.2, JP–H=0.4Hz, 6H); 13C-NMR (100MHz, CDCl3) δ:
2
191.81 (d, JP–C=6.7Hz), 135.80, 133.89, 132.40, 131.45, 129.79,
2
128.87, 128.48, 127.76, 126.89, 124.17, 62.67 (d, JP–C=6.6Hz),
1
3
38.63 (d, JP–C=129.0Hz), 16.26 (d, JP–C=6.3Hz); IR (neat):
2984, 2916, 1674, 1289, 1248, 1024, 965, 813cm−1; HR-MS
Yellow oil; 1H-NMR (400MHz, CDCl3) δ: 8.01–7.99 (m,
(ESI, TFA-Na): Calcd for C16H19NaO4P [M+Na]+ 329.0919, 2H), 7.59–7.56 (m, 1H), 7.49–7.45 (m, 2H), 4.23–4.01 (m, 5H),
3
3
found 329.0910.
1.54 (dd, JP–H=18.0Hz, J=7.2Hz, 3H), 1.28 (t, J=7.2, 3H),
Diethyl (2-(4-Fluorophenyl)-2-oxoethyl)phosphonate (3i)46)
1.19 (t, J=7.2, 3H); 13C-NMR (100MHz, CDCl3) δ: 196.49
2
3
(d, JP–C=5.2Hz), 136.85 (d, JP–C=1.8Hz), 133.31, 128.84,
128.48, 62.71 (d, JP–C=6.9Hz), 62.60 (d, JP–C=6.7Hz),
2
2
1
3
41.31 (d, JP–C=129.8Hz), 16.33 (d, JP–C=6.1Hz), 16.18 (d,
3JP–C=6.2Hz), 12.22 (d, JP–C=6.5Hz); IR (neat): 2988, 2923,
2
1680, 1450, 1265, 1024, 970, 803cm−1; HR-MS (ESI, TFA-Na):
Calcd for C13H19NaO4P [M+Na]+ 293.0919, found 293.0907.
Yellow oil; 1H-NMR (400MHz, CDCl3) δ: 8.07–8.04 (m, 2H),