Page 192 - 201901

·178· 精细化工 FINE CHEMICALS 第 36 卷

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固体，收率 64.3%，熔点 115~117 ℃。 HNMR (400 270.8856。
MHz, Chloroform-d), δ: 7.43~7.35 (m, 2H), 7.12 (d, N-(3-溴苯基)-四氢呋喃-3-甲酰胺（Ⅸ）：白色固
J=8.2 Hz, 2H), 4.09~4.00 (m, 2H), 3.98~3.93 (m, 1H), 体，收率 88.1%，熔点 71~73 ℃。HNMR (400 MHz,
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3.91~3.80 (m, 1H), 3.12~2.94 (m, 1H), 2.31 (s, 3H), Chloroform-d), δ: 7.80 (s, 1H), 7.71 (t, J=2.0 Hz, 1H),
13
2.26 (m, 2H); CNMR (101 MHz, Chloroform-d), δ:
171.91, 135.18, 134.09, 129.51(2C), 119.98(2C), 7.34 (m, 1H), 7.21~7.14 (m, 1H), 7.09 (t, J=8.0 Hz,
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71.02, 68.21, 46.55, 30.64, 20.89。IR (KBr), v/cm : 1H), 4.03~3.93 (m, 2H), 3.86 (m, 1H), 3.77 (m, 1H),
13
2.98 (m, 1H), 2.18 (q, J=7.2 Hz, 2H); CNMR (101
3282, 3031, 2958, 2923, 2862, 1653, 1606, 1584, 1494, MHz, Chloroform-d), δ: 172.39, 139.07, 130.31,
+
1451, 1114。 HRMS (ESI, m/Z): [M+H] caled for 127.40, 122.93, 122.61, 118.44, 70.92, 68.19, 46.44,
+
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[C 12 H 16 NO 2 ] 206.1136, found 206.1140。 30.57。IR (KBr), v/cm : 3285, 3057, 2958, 2925, 2862,
N-(2-氟苯基)-四氢呋喃-3-甲酰胺（Ⅴ）：白色固 1657, 1583, 1538, 1475, 1444, 1066。HRMS (ESI,
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+
+
体，收率 93.2%，熔点 112~114 ℃。HNMR (400 MHz, m/Z): [M+H] caled for [C 11 H 13 BrNO 2 ] 271.0031,
Chloroform-d), δ: 8.20~7.94 (m, 2H), 7.03~6.87 (m, found 271.0006。
3H), 3.99~3.82 (m, 3H), 3.79~3.66 (m, 1H), 3.05 (m, N-(4-硝基苯基)-四氢呋喃-3-甲酰胺（Ⅹ）：黄色
1H), 2.23~2.03 (m, 2H); 13 CNMR (101 MHz, 1
Chloroform-d), δ: 172.48, 154.17, 151.75 126.04, 固体，收率 54.3%，熔点 243~245 ℃。 HNMR (400
124.86, 124.39, 122.69, 114.96, 70.91, 68.27, 46.09, MHz, Chloroform-d), δ: 8.27~8.18 (m, 2H), 7.88 (s,
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30.56。IR (KBr), v/cm : 3268, 3047, 2958, 2863, 1658, 1H), 7.76~7.69 (m, 2H), 4.16~4.03 (m, 2H), 3.97~3.80
13
+
1583, 1543, 1456, 1108。HRMS (ESI, m/Z): [M+H] (m, 2H), 3.11 (m, 1H), 2.31 (m, 2H); CNMR (101
MHz, Chloroform-d), δ: 172.82, 144.06, 143.38,
+
caled for [C 11 H 13 FNO 2 ] 210.0886, found 210.0847。 132.49, 131.97, 128.83, 125.05, 119.20, 70.85, 68.16,
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N-(2,4-二氟苯基)-四氢呋喃-3-甲酰胺（Ⅵ）：白 46.55, 30.48。IR (KBr), v/cm : 3284, 3079, 2958,
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色固体，收率 82.5%，熔点 105~106 ℃。HNMR (400 2923, 2868, 1656, 1601, 1584, 1543, 1509, 1445, 1327,
+
+
MHz, Chloroform-d), δ: 8.20 (m, 1H), 7.64 (s, 1H), 1114。HRMS (ESI, m/Z): [M+H] caled for [C 11 H 13 N 2 O 4 ]
6.95~6.80 (m, 2H), 4.10~4.00 (m, 2H), 3.96 (m, 1H), 237.0831, found 237.0687。
3.86 (m, 1H), 3.10(m, 1H), 2.27 (q, J=7.1 Hz, 2H);
13 CNMR (101 MHz, Chloroform-d), δ: 172.15, 123.13, N-(2-甲基-3-氯苯基)-四氢呋喃-3-甲酰胺（Ⅺ）：
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111.23, 103.83, 103.58, 103.33, 77.26, 70.88, 68.12, 白色固体，收率 90.3%，熔点 145~146 ℃。 HNMR
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46.47, 30.56。IR (KBr), v/cm : 3260, 3028, 2981,2958, (400 MHz, Chloroform-d), δ: 7.73 (s, 1H), 7.52(d,
J=8.0Hz, 1H), 7.19 (m, 1H), 7.08 (t, J=8.0 Hz, 1H),
2858, 1661, 1603, 1538, 1505, 1458, 1100。HRMS 4.09~3.97 (m, 2H), 3.94~3.80 (m, 2H), 3.14~3.01 (m,
+
+
(ESI, m/Z): [M+H] caled for [C 11H 12F 2NO 2 ] 227.0758, 1H), 2.32~2.19 (m, 5H); 13 CNMR (101 MHz,
found 227.0546。 Chloroform-d), δ: 172.60, 136.59, 134.88, 128.77,
N-(2-氯苯基)-四氢呋喃-3-甲酰胺（Ⅶ）：白色固 126.85, 126.51, 122.62, 70.99, 68.04, 46.13, 30.53,
1
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体，收率 86.2%，熔点 106~108 ℃。HNMR (400 MHz, 14.60。IR (KBr), v/cm : 3285, 3054, 2958, 2925, 2862,
Chloroform-d), δ: 8.26 (m, 1H), 7.94 (s, 1H), 7.30 (m, 1657, 1604, 1583, 1504, 1447,1108。HRMS (ESI，m/Z):
1H), 7.24~7.15 (m, 1H), 6.98 (m, 1H), 4.10~3.93 (m, [M+H] caled for [C 12 H 15 ClNO 2 ] 241.0684, found
+
+
2H), 3.88 (m, 1H), 3.85~3.77 (m, 1H), 3.11~2.99 (m, 241.0841。
1H), 2.30~2.16 (m, 2H); 13 CNMR (101 MHz, N-(2-甲基 -6-乙基苯基 )-四氢呋喃 -3-甲酰胺
Chloroform-d), δ: 172.23, 134.50, 129.04, 127.74,
124.82, 122.95, 121.81, 70.87, 68.02, 46.87, 30.56。IR （Ⅻ）：白色固体，收率 71.4%，熔点 130~132 ℃。
1 HNMR (400 MHz, Chloroform-d), δ: 7.23(s, 1H),
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(KBr), v/cm : 3280, 3043, 2958, 2862, 1659, 1585,
+
1538, 1474, 1445, 1104。HRMS (ESI, m/Z): [M+H] 7.06 (d, J=7.5 Hz, 1H), 7.02~6.96 (m, 2H), 4.00 (m,
1H), 3.93 (m, 1H), 3.85 (m, 1H), 3.76 (m, 1H), 3.03
+
caled for [C 11 H 13 ClNO 2 ] 227.0527, found 227.0545。 (m, 1H), 2.45 (q, J=7.6 Hz, 2H), 2.22~2.16 (m, 2H),
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N-(2-溴苯基)-四氢呋喃-3-甲酰胺（Ⅷ）：白色固 2.10 (s, 3H), 1.08 (t, J=7.6 Hz, 3H); CNMR (101
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体，收率 91.2%，熔点 85~87 ℃。HNMR (400 MHz, MHz, Chloroform-d), δ: 172.58, 141.03, 135.84,
Chloroform-d), δ: 8.23 (m, 1H), 7.92 (s, 1H), 7.46 (m, 132.96, 128.67, 128.24, 127.68, 126.32, 71.03, 68.09,
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1H), 7.28~7.19 (m, 1H), 6.91 (m, 1H), 4.12~3.93 (m, 45.63, 30.52, 24.87, 18.37, 14.46。IR (KBr), v/cm :
2H), 3.87(m, 1H), 3.84~3.76 (m, 1H), 3.13~2.99 (m, 3285, 3057, 2958, 2934, 2925, 2862, 1657, 1602, 1588,
+
1H), 2.30~2.16 (m, 2H); 13 CNMR (101 MHz, 1504, 1449, 1068; HRMS (ESI, m/Z): [M+H] caled
+
Chloroform-d), δ: 172.20, 135.61, 132.28, 128.38, for [C 14 H 20 NO 2 ] 234.1449, found 234.1226。
125.36, 122.17, 113.63, 70.82, 68.00, 46.88, 30.52。IR N-(4-甲氧基苯基)-四氢呋喃-3-甲酰胺（ⅩⅢ）：
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(KBr), v/cm : 3278, 3057, 2958, 2925, 2862, 1657, 黄色固体，收率 67.2%，熔点 126~127 ℃。 HNMR
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1603, 1583, 1485, 1444, 1106。HRMS (ESI，m/Z): (400 MHz, Chloroform-d), δ 7.45~7.39 (m, 2H),
+
+
[M+H] caled for [C 11 H 13 BrNO 2 ] 271.0031, found 6.88~6.82 (m, 2H), 4.05~3.98 (m, 2H), 3.98~3.91 (m,