36
J. Galeta et al./Chemical Papers 67 (1) 29–39 (2013)
Table 2. (continued)
Compound
Spectral dataa
—
—
Xb
IR, ν˜/cm−1: 1035, 1166, 1237 (P O), 1393, 1461, 1733 (C N), 2874, 2911, 2934, 2964, 3163 (NH)
—
—
3
3
1H NMRb (CDCl3), δ: 0.83 (t, JH,H = 7.4 Hz, 3H, CH2—CH2—CH3), 1.24 (t, JH,H = 7.1 Hz, 6H, O—CH2—
3
CH3), 1.41 (qm, JH,H = 7.4 Hz, 2H, CH2—CH2—CH3), 2.03–2.14 (m, 2H, CH2—CH2—CH3), 3.95–4.12 (m, 4H,
3
2
O—CH2), 7.12 (t, JH,H = 5.7 Hz, 1H, CH), 8.21 (d, JH,P = 27.2 Hz, 1H, NH)
3
13C NMRb (CDCl3), δ: 13.5 (CH2—CH2—CH3), 16.0 (d, JC,P = 6.9 Hz, O—CH2—CH3), 19.9 (CH2—CH2—
2
3
CH3), 34.0 (CH2—CH2—CH3), 62.9 (d, JC,P = 5.5 Hz, O—CH2), 148.5 (d, JC,P = 18.5 Hz, CH)
1H NMRc (CDCl3), δ: 0.89 (t, 3JH,H = 7.4 Hz, 3H, CH2—CH2—CH3), 1.26 (t, 3JH,H = 7.1 Hz, 6H, O—CH2—CH3),
1.47 (qm, 3JH,H = 7.4 Hz, 2H, CH2—CH2—CH3), 2.20 (td, 3JH,H = 7.4 Hz, 3JH,H = 1.2 Hz, 2H, CH2—CH2—CH3),
3
2
3.95–4.12 (m, 4H, O—CH2), 6.53 (t, JH,H = 5.3 Hz, 1H, CH), 8.36 (d, JH,P = 27.2 Hz, 1H, NH)
3
13C NMRc (CDCl3), δ: 13.6 (CH2—CH2—CH3), 16.1 (d, JC,P = 6.8 Hz, O—CH2—CH3), 19.3 (CH2—CH2—
2
3
CH3), 28.0 (CH2—CH2—CH3), 63.0 (d, JC,P = 5.5 Hz, O—CH2), 148.0 (d, JC,P = 17.8 Hz, CH)
GC-MS, m/z (%): 222 (M+, 10), 126 (40), 98 (30), 70 (100), 55 (20)
HRMS, m/z (found/calc.): 223.1221/223.1206 (C8H20N2O3P+
)
—
—
Xc
IR, ν˜/cm−1: 1041, 1083, 1160, 1247 (P O), 1391, 1451, 1478, 1631 (C N), 2848, 2906, 2982, 3129 (NH)
—
—
3
1H NMR (CDCl3), δ: 1.33 (t, JH,H = 6.7 Hz, 6H, CH3), 1.62–1.77 (m, 12H, Ad), 1.97–2.02 (m, 3H, Ad), 4.06–4.20
2
—
—
(m, 4H, O—CH2), 6.86 (s, 1H, HC N), 7.12 (d, JH,P = 26.6 Hz, 1H, NH)
13C NMR (CDCl3), δ: 16.4 (d, JC,P = 6.7 Hz, CH3), 28.2 (CH, Ad), 36.7 (C, Ad), 36.9 (CH2, Ad), 40.3 (CH2,
3
2
3
—
Ad), 63.4 (d, JC,P = 5.6 Hz, O—CH2), 155.5 (d, JC,P = 17.0 Hz, HC N)
—
GC-MS, m/z (%): 314 (M+, 1), 153 (44), 126 (100), 98 (58), 81 (24)
3
Xd
Xe
1H NMR (CDCl3), δ: 1.37 (t, JH,H = 6.9 Hz, 6H, CH3), 4.12–4.26 (m, 4H, CH2), 6.98–7.02 (m, 1H, CH), 7.11–7.16
2
—
—
(m, 1H, CH), 7.25–7.29 (m, 1H, CH), 8.00 (s, 1H, HC N), 8.28 (d, JH,P = 27.6 Hz, 1H, NH)
13C NMR (CDCl3), δ: 16.3 (d, JC,P = 6.8 Hz, CH3), 63.8 (d, JC,P = 5.9 Hz, CH2), 127.1 (CH), 127.4 (CH),
128.2 (CH), 139.6 (d, JC,P = 19.8 Hz, HC N), 139.8 (C)
GC-MS, m/z (%): 262 (M+, 15), 153 (16), 126 (83), 109 (22), 98 (100), 81 (53)
IR, ν˜/cm−1: 1030, 1242 (P O), 1317, 1456, 1660 (C N), 2941, 2981, 3012, 3138 (NH)
1H NMRb (CDCl3), δ: 1.29 (t, JH,H = 7.1 Hz, 6H, CH3), 3.50 (d, JH,H = 5.8 Hz, 2H, Ph—CH2), 4.02–4.16 (m,
4H, O—CH2), 7.12–7.30 (m, 5H, Ph), 7.31 (t, JH,H = 5.8 Hz, 1H, N CH), 8.78 (d, JH,P = 27.7 Hz, 1H, NH)
13C NMRb (CDCl3), δ: 15.9 (d, JC,P = 6.8 Hz, CH3), 38.6 (Ph—CH2), 62.7 (d, JC,P = 5.4 Hz, O—CH2), 126.4
3
2
3
—
—
—
—
—
—
3
3
3
2
—
—
3
2
3
—
—
(CH), 128.4 (2 × CH), 128.6 (2 × CH), 136.8 (C), 146.5 (d, JC,P = 19.0 Hz, N CH)
1H NMRc (CDCl3), δ: 1.11 (t, JH,H = 7.0 Hz, 6H, CH3), 3.64 (d, JH,H = 5.2 Hz, 2H, Ph—CH2), 3.86–3.96 (m,
3
3
3
2
—
—
4H, CH2), 6.76 (t, JH,H = 5.2 Hz, 1H, N CH), 7.12–7.30 (m, 5H, Ph), 8.93 (d, JH,P = 28.6 Hz, 1H, NH)
13C NMRc (CDCl3), δ: 15.7 (d, JC,P = 6.8 Hz, CH3), 35.0 (Ph—CH2), 63.2 (d, JC,P = 6.2 Hz, CH2), 126.0
3
2
3
—
—
(CH), 128.1 (2 × CH), 128.3 (2 × CH), 135.9 (C), 148.2 (d, JC,P = 19.6 Hz, N CH)
GC-MS, m/z (%): 270 (M+, 80), 242 (20), 153 (20), 126 (90), 98 (100), 81 (40)
—
—
Xf
Xg
Xh
Xi
IR, ν˜/cm−1: 1032, 1066, 1168, 1226 (P O), 1369, 1391, 1482, 1532, 1615 (C N), 2814, 2905, 2941, 2986, 3136
—
—
(NH)
3
1H NMR (CDCl3), δ: 1.33 (t, JH,H = 7.0 Hz, 6H, CH3), 2.99 (s, 6H, N—CH3), 4.13–4.26 (m, 4H, CH2), 6.68 (d,
3
JH,H = 8.7 Hz, 2H, Ph), 7.49 (d, 3JH,H = 8.7 Hz, 2H, Ph), 7.56 (d, 2JH,P = 27.0 Hz, 1H, NH), 7.71 (s, 1H, HC N)
—
—
3
2
13C NMR (CDCl3), δ: 16.4 (d, JC,P = 6.9 Hz, CH3), 40.5 (N—CH3), 63.4 (d, JC,P = 5.5 Hz, CH2), 112.1 (CH),
3
—
122.8 (C), 128.2 (CH), 145.6 (d, JC,P = 18.9 Hz, HC N), 151.4 (C)
—
GC-MS, m/z (%): 299 (M+, 38), 162 (12), 146 (100), 126 (24), 98 (35), 81 (15)
IR, ν˜/cm−1: 1032, 1236 (P O), 1479, 1610, 2818, 2837, 2931, 2958, 3116 (NH)
1H NMR (CDCl3), δ: 1.36 (t, JH,H = 7.1 Hz, 6H, CH3), 3.82 (s, 3H, O—CH3), 4.03–4.37 (m, 4H, CH2), 6.88 (d,
—
—
3
3
3
2
—
JH,H = 8.8 Hz, 2H, Ph), 7.55 (d, JH,H = 8.8 Hz, 2H, Ph), 7.82 (s, 1H, HC N), 8.43 (d, JH,P = 28.1 Hz, 1H,
—
NH)
3
2
13C NMR (CDCl3), δ: 16.3 (d, JC,P = 7.1 Hz, CH3), 55.5 (O—CH3), 63.5 (d, JC,P = 5.1 Hz, CH2), 114.1 (CH),
3
—
127.6 (C), 128.2 (CH), 144.8 (d, JC,P = 19.2 Hz, HC N), 160.7 (C)
—
GC-MS, m/z (%): 286 (M+, 17), 153 (19), 126 (100), 109 (21), 98 (87), 81 (44)
IR, ν˜/cm−1: 1036, 1092, 1240 (P O), 1485, 2827, 2866, 2943, 2980, 3149 (NH)
1H NMR (CDCl3), δ: 1.36 (t, JH,H = 7.1 Hz, 6H, CH3), 2.35 (s, 3H, Ph—CH3), 4.09–4.31 (m, 4H, CH2), 7.16 (d,
—
—
3
3
3
2
—
JH,H = 7.9 Hz, 2H, Ph), 7.50 (d, JH,H = 7.9 Hz, 2H, Ph), 7.81 (s, 1H, HC N), 8.22 (d, JH,P = 28.1 Hz, 1H,
—
NH)
3
2
13C NMR (CDCl3), δ: 16.3 (d, JC,P = 7.1 Hz, CH3), 21.6 (Ph—CH3), 63.6 (d, JC,P = 6.1 Hz, CH2), 126.8 (CH),
3
—
129.5 (CH), 132.1 (C), 139.6 (C), 145.1 (d, JC,P = 19.2 Hz, HC N)
—
GC-MS, m/z (%): 270 (M+, 8), 153 (16), 126 (67), 98 (100), 81 (55)
IR, ν˜/cm−1: 1034, 1087, 1242 (P O), 1483, 2846, 2866, 2939, 2983, 3128 (NH)
1H NMR (CDCl3), δ: 1.37 (t, JH,H = 7.1 Hz, 6H, CH3), 4.08–4.31 (m, 4H, CH2), 7.31 (d, JH,H = 8.4 Hz, 2H,
Ph), 7.54 (d, JH,H = 8.4 Hz, 2H, Ph), 7.86 (s, 1H, HC N), 8.97 (d, JH,P = 28.7 Hz, 1H, NH)
13C NMR (CDCl3), δ: 16.3 (d, JC,P = 6.1 Hz, CH3), 63.6 (d, JC,P = 6.1 Hz, CH2), 127.9 (CH), 128.9 (CH),
—
—
3
3
3
2
—
—
3
2
3
—
133.4 (C), 135.1 (C), 143.8 (d, JC,P = 20.2 Hz, HC N)
—
GC-MS, m/z (%): 290 (M+, 7), 153 (18), 126 (100), 109 (21), 98 (90), 89 (19), 81 (48)