Page 143 - 精细化工2019年第9期

第 9 期 杨家强，等: 含膦酸酯结构单元的磺胺衍生物合成与抗菌活性 ·1871·

OCH 2 ), 1.36(t, 3H, J=16.0 Hz, CH 3 ), 1.01(t, 3H, 160.9, 162.2, 163.4。
13
J=12.0 Hz, CH 3 ); CNMR (100 MHz, CDCl 3 ), δ: 16.0, N-[(二乙氧基膦酰基)-苯甲基]-4-甲基苯磺酰胺
16.4, 48.5, 63.9, 64.5, 114.7, 114.9, 121.1, 124.0,
126.8, 128.3, 129.5, 132.0, 140.3, 161.8。 (Ⅱg): 白色固体, 收率 50.2%，m. p. 102~104 ℃。
–1
IR (KBr), v/cm : 3063, 2982, 2867, 1600, 1459, 1318,
N-[(二乙氧基膦酰基)-4-氟苯甲基]-苯磺酰胺 1
1227, 1161, 1092, 1053, 1023; HNMR (400 MHz,
(Ⅱc): 白色固体, 收率 45.0%,m. p. 141~142 ℃。IR CDCl 3 ), δ: 7.42(d, 2H, J = 8.0 Hz, ArH), 6.94~7.24(m,
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(KBr), v/cm : 3129, 2983, 2930, 2888, 1607, 1514, 7H, ArH), 6.52(s, 1H, NH), 4.71(q, 1H, J=36.0 Hz,
1458, 1394, 1340, 1239, 1163, 1093, 1050, 1019; PCH), 4.16~4.23(m, 2H, OCH 2 ), 3.79~3.85(m, 1H,
1
HNMR (400 MHz, CDCl 3 ), δ: 7.72~7.82(m, 1H, ArH), OCH 2 ), 3.51~3.58(m, 1H, OCH 2 ), 2.25(s, 3H, CH 3 ),
7.54(d, 2H, J=8.0 Hz, ArH), 7.11~7.30(m, 5H, ArH), 1.30(t, 3H, J=16.0 Hz, CH 3 ), 0.99(t, 3H, J=12.0 Hz,
13
6.67~6.72(m, 2H, ArH+NH), 4.77(q, 1H, J=32.0 Hz, CH 3 ); CNMR (100 MHz, CDCl 3 ), δ: 16.0, 16.3, 21.3,
PCH), 4.25~4.29(m, 2H, OCH 2 ), 3.84~3.88(m, 1H, 54.4, 55.9, 63.5, 63.6, 127.0, 127.7, 127.8, 128.0,
OCH 2 ), 3.58~3.68(m, 1H, OCH 2 ), 1.35(t, 3H, J=16.0 128.1, 128.2, 128.8, 128.9, 133.5, 137.4, 139.9, 142.8。
13
Hz, CH 3 ), 1.02(t, 3H, J=16.0 Hz, CH 3 ); CNMR (100 N-[(二乙氧基膦酰基)-2-氟苯甲基]-4-甲基苯磺
MHz, CDCl 3 ), δ: 16.1, 16.5, 53.8, 63.5, 64.3, 114.8,
115.0, 126.8, 128.2, 129.3, 129.9, 132.0, 160.9, 163.4。 酰胺(Ⅱh): 白色固体, 收率 47.3%，m. p. 137~138 ℃。
–1
IR (KBr), v/cm : 3129, 2985, 2886, 1617, 1590, 1606,
N-[(二乙氧基膦酰基)-苯甲基]-4-甲氧基苯磺酰
1497, 1457, 1394, 1341, 1289, 1241, 1185, 1092, 1050,
胺(Ⅱd): 白色固体, 收率 44.6%，m. p. 115~116 ℃。 1018; HNMR (400 MHz, CDCl 3), δ: 6.77~7.49(m, 9H,
1
–1
IR (KBr), v/cm : 3120, 2982, 2934, 2882, 1597, 1498, ArH+NH), 5.11~5.19(q, 1H, J=32.0 Hz, PCH), 4.24~
1459, 1333, 1259, 1235, 1160, 1094, 1051, 1023; 4.28(m, 2H, OCH 2 ), 3.87~3.91(m, 1H, OCH 2 ), 3.68~
1 HNMR (400 MHz, CDCl 3 ), δ: 7.46(d, 2H, J = 8.0 Hz, 3.72(m, 1H, OCH 2 ), 2.22(s, 3H, CH 3 ), 1.34(t, 3H,
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ArH), 7.04~7.24(m, 5H, ArH), 6.65(s, 1H, NH), J=8.0 Hz, CH 3 ), 1.03(t, 3H, J=8.0 Hz, CH 3 ); CNMR
6.58~6.62(m, 2H, ArH), 4.72(q, 1H, J=32.0 Hz, PCH), (100 MHz, CDCl 3 ), δ: 16.0, 16.4, 21.3, 46.5, 63.6,
4.18~4.26(m, 2H, OCH 2 ), 3.83~3.85(m, 1H, OCH 2 ), 64.3, 114.7, 114.9, 121.2, 124.0, 126.9, 128.9, 129.4,
3.72(s, 3H, OCH 3 ), 3.53~3.60(m, 1H, OCH 2 ), 1.32(t, 129.5, 135.8, 142.9, 158.9。
3H, J=12.0 Hz, CH 3 ), 0.99(t, 3H, J=12.0 Hz, CH 3 ); N-[(二乙氧基膦酰基)-4-氟苯甲基]-4-甲基苯磺
13 CNMR (100 MHz, CDCl 3 ), δ: 16.0, 16.4, 54.4, 55.4,
63.5, 64.0, 113.4, 127.7, 127.8, 128.1, 128.2, 128.3, 酰胺(Ⅱi): 白色固体, 收率 52.2%, m. p. 125~127 ℃。
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129.0, 132.4, 133.4, 162.3。 IR (KBr), v/cm : 3248, 2976, 2928, 2867, 1659, 1606,
1536, 1511, 1455, 1393, 1308, 1242, 1161, 1115, 1097,
N-[(二乙氧基膦酰基)-2-氟苯甲基]-4-甲氧基苯 1029; HNMR (400 MHz, CDCl 3 ), δ: 7.00~7.56(m, 9H,
1
磺酰胺(Ⅱe): 白色固体, 收率 42.9%, m. p. 138~ ArH+NH), 5.62~5.70(q, 1H, J=32.0 Hz, PCH),
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140 ℃。IR (KBr), v/cm : 3141, 2989, 2886, 2846, 4.01~4.07(m, 2H, OCH 2 ), 3.83~3.87(m, 1H, OCH 2 ),
1597, 1496, 1457, 1392, 1338, 1261, 1238, 1159, 1098, 3.59(m, 1H, OCH 2 ), 2.34(s, 3H, CH 3 ), 1.25(t, 3H,
1
1064, 1024; HNMR (400 MHz, CDCl 3 ), δ: 7.51(d, 2H, J=12.0 Hz, CH 3 ), 1.05(m, 3H, J=12.0 Hz, CH 3 );
13
J=8.0 Hz, ArH), 6.81~7.24(m, 5H, ArH+NH), 6.61~ CNMR (100 MHz, CDCl 3 ), δ: 16.1, 16.3, 18.2, 48.7,
6.63(q, 2H, J=8.0 Hz, ArH), 5.08(q, 1H, J=32.0 Hz, 62.9, 63.5, 115.4, 115.6, 125.6, 126.9, 129.8, 135.4,
PCH), 4.23~4.26(m, 2H, OCH 2 ), 3.87~3.91(m, 1H, 136.2, 161.2, 163.7。
OCH 2 ), 3.67~3.73(m, 4H, OCH 2 +CH 3 ), 1.34(t, 3H, N-[(二乙氧基膦酰基)-苯甲基]-4-氟苯磺酰胺
J=12.0 Hz, CH 3 ), 1.01(t, 3H, J=12.0 Hz, CH 3 ); (Ⅱj): 白色固体, 收率 52.1%，m. p. 150~151 ℃。IR
13 CNMR (100 MHz, CDCl 3 ), δ: 15.9, 16.4, 47.2, 63.6, (KBr), v/cm : 3141, 2986, 2930, 2885, 1605, 1500,
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64.2, 113.5, 114.8, 115.1, 121.0, 121.4, 124.1, 129.0, 1461, 1337, 1260, 1234, 1166, 1092, 1055, 1026;
129.5, 131.7, 160.8, 162.7。 1 HNMR (400 MHz, CDCl 3 ), δ: 6.88~7.56(m, 10H,
N-[(二乙氧基膦酰基)-4-氟苯甲基]-4-甲氧基苯 ArH+NH), 4.78(q, 1H, J=32.0 Hz, PCH), 4.22~4.29(m,
磺酰胺(Ⅱf): 白色固体, 收率 43.2%，m. p. 106~ 2H, OCH 2 ), 3.84~3.89(m, 1H, OCH 2 ), 3.50~3.57(m,
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108 ℃。IR (KBr), v/cm : 3117, 2987, 2935, 2884, 1H, OCH 2 ), 1.30(t, 3H, J=16.0 Hz, CH 3 ), 1.01(t, 3H,
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J=12.0 Hz, CH 3 ); CNMR (100 MHz, CDCl 3 ), δ: 16.0,
1597, 1513, 1456, 1393, 1336, 1303, 1258, 1235, 1161, 16.4, 54.4, 55.4, 63.5, 64.0, 114.2, 114.4, 127.7, 127.8,
1
1095, 1049, 1016; HNMR (400 MHz, CDCl 3 ), δ: 128.1, 128.2, 128.8, 128.9, 129.0, 132.4, 133.4, 162.3。
7.44(d, 2H, J=12.0 Hz, ArH), 7.03~7.24(m, 3H,
ArH+NH), 6.73(d, 2H, J=16.0 Hz, ArH), 6.61(d, 2H, N-[(二乙氧基膦酰基)-2-氟苯甲基]-4-氟苯磺酰
J=8.0 Hz, ArH), 4.70(q, 1H, J=36.0 Hz, PCH), 胺(Ⅱk): 白色固体, 收率 51.4%，m. p. 129 ~ 130 ℃。
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4.20~4.24(m, 2H, OCH 2 ), 3.84~3.88(m, 1H, OCH 2 ), IR (KBr), v/cm : 3132, 2982, 2925, 2885, 1608, 1590,
3.60~3.71(m, 4H, OCH 2 +CH 3 ), 1.32(t, 3H, J=12.0 Hz, 1532, 1495, 1455, 1389, 1308, 1226, 1182, 1091, 1055,
1
CH 3 ), 1.02(t, 3H, J=16.0 Hz, CH 3 ); 13 CNMR (100 1010; HNMR (400 MHz, CDCl 3 ), δ: 6.75~7.80(m, 9H,
MHz, CDCl 3 ), δ: 16.0, 16.4, 55.3, 63.5, 64.2, 113.5, ArH+NH), 5.20~5.28(q, 1H, J=32.0 Hz, PCH), 4.26~
114.9, 115.1, 129.0, 129.4, 129.5,129.8, 130.0, 132.3, 4.40(m, 2H, OCH 2 ), 3.82~3.88(m, 1H, OCH 2 ), 3.70~