Page 128 - 201901

·114· 精细化工 FINE CHEMICALS 第 36 卷

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IR (KBr), v/cm : 3424, 3116, 1619, 1551 cm ; 2H), 1.72 (d, J=10.5 Hz, 1H), 1.37 (dd, J=13.0、9.0 Hz,
1 13
HNMR (400 MHz, CDCl 3 )，δ: 7.62 (d, J=8.5 Hz, 2H), 1H), 1.24 (s, 3H), 0.49 (s, 3H); CNMR (100 MHz,
7.23 (d, J=8.6 Hz, 2H), 7.03 (d, J=8.6 Hz, 2H), 6.70 (d, CDCl 3), δ: 165.71, 165.21, 151.96, 149.92, 135.46,
J=7.7 Hz, 1H), 6.66 (d, J=8.7 Hz, 2H), 5.76 (d, J= 128.43, 128.04, 127.39, 126.24, 124.34, 112.41, 101.85,
11.9 Hz, 1H), 3.92 (dd, J=21.3、9.6 Hz, 1H), 2.94 (t, 65.50, 45.78, 45.07, 41.34, 40.74, 26.64, 23.59, 21.83;
+
J=4.2 Hz, 1H), 2.91 (s, 6H), 2.51 (m, 1H), 2.09~ HRMS, m/Z: calcd for C 27 H 30 N 4 S [M+H] : 443.2269;
1.92 (m, 2H), 1.75 (d, J=10.5 Hz, 1H), 1.40 (dd, found: 443.2260。
J=13.1、9.1 Hz, 1H), 1.26 (d, J=7.2 Hz, 3H), 0.52 (s, 2-{2-[3-(4-二甲氨基亚苄基)-6,6-二甲基双环
13
3H); CNMR (100 MHz, CDCl 3 ), δ: 166.00, 165.33, [3.1.1]庚-2-亚基]肼基} -4-(3,4-二氯苯基)噻唑(4j):
150.84, 149.97, 133.98, 133.01, 128.59, 128.05, 127.55, 白色粉末，收率 69.2%，质量分数 98.8%。m. p. 218~
124.21, 112.42, 102.24, 65.55, 45.87, 45.13, 41.36, 1
40.76, 26.66, 23.61, 21.86; HRMS, m/Z: calcd for 219 ℃; IR (KBr), v/cm : 3429, 3149, 1617, 1549;
+
C 27 H 29 ClN 4 S [M+H] : 477.1880; found: 477.1833。 1 HNMR (400 MHz, CDCl 3 ), δ: 7.77 (s, 1H), 7.49 (d,
J=6.4 Hz, 1H), 7.31 (d, J=7.0 Hz, 1H), 7.03 (d, J=
2-{2-[3-(4-二甲氨基亚苄基)-6,6-二甲基双环
8.3 Hz, 1H), 6.92 (d, J=8.3 Hz, 1H), 6.71 (d, J=7.9 Hz,
[3.1.1]庚-2-亚基]肼基}-4-(4-羟基苯基)噻唑(4g): 白 1H), 6.64 (dd, J=14.2、8.5 Hz, 2H), 5.72 (dd, J=23.8、
色粉末，收率 82.7%，质量分数 99.4%。m. p. 212~ 11.0 Hz, 1H), 4.03~3.85 (m, 1H), 2.95 (d, J=12.8 Hz,
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214 ℃; IR (KBr), v/cm : 3400, 3228, 3112, 1615, 1549; 1H), 2.89 (d, J=8.6 Hz, 6H), 2.64~2.47 (m, 1H),
1 2.08~1.91 (m, 2H), 1.75 (d, J=10.5 Hz, 1H), 1.52~
HNMR (400 MHz, CDCl 3)，δ: 7.45 (t, J=7.1 Hz, 2H),
6.99 (d, J=8.6 Hz, 1H), 6.88 (d, J=8.6 Hz, 1H), 1.32 (m, 3H), 1.27 (s, 2H), 1.06 (s, 1H), 0.52 (s, 1H);
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6.70~6.62 (m, 1H), 6.62~6.55 (m, 3H), 6.52 (d, J= CNMR (100 MHz, CDCl 3)，δ: 165.96, 165.16, 149.89,
5.6 Hz, 1H), 5.78 (d, J=18.9Hz, 1H), 4.01~3.82 (m, 149.41, 135.29, 132.28, 130.72, 130.13, 128.47, 127.94,
1H), 2.92 (t, J=4.9 Hz, 1H), 2.85 (d, J=5.5 Hz, 5H), 127.87, 125.24, 125.15, 112.23, 103.33, 103.05, 65.40,
2.53 (m, 1H), 2.06~1.92 (m, 2H), 1.74 (d, J=10.4 Hz, 44.94, 40.40, 32.87, 26.50, 23.38, 21.67; HRMS, m/Z:
+
1H), 1.40 (m, 1H), 1.33 (s, 1H), 1.26 (s, 2H), 1.25~ calcd for C 27 H 28 Cl 2 N 4 S [M+H] : 511.1490; found:
1.19 (m, 1H), 1.05 (s, 1H), 0.90~0.81 (m, 1H), 0.49 (s, 511.1463。
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2H); CNMR (100 MHz, CDCl 3 ), δ: 165.71, 165.33, 2-{2-[3-(4-二甲氨基亚苄基)-6, 6-二甲基双环
155.42, 151.63, 149.70, 128.55, 127.95, 127.50, 115.22, [3.1.1]庚-2-亚基]肼基}-4-(3-硝基苯基)噻唑(4k): 黄
112.38, 100.26, 99.88, 68.87, 65.34, 44.87, 40.61, 色粉末，收率 83.7%，质量分数 95.6%。m. p. 229~
40.45, 32.80, 26.49, 23.28, 21.63; HRMS, m/Z: calcd
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for C 27 H 30 N 4 OS [M+H] : 459.2219; found: 459.2220。 230 ℃; IR (KBr), v/cm : 3468, 3163, 1617, 1549;
1 HNMR (400 MHz, CDCl 3 ), δ: 8.55~8.40 (m, 1H),
2-{2-[3-(4-二甲氨基亚苄基)-6,6-二甲基双环
8.07~7.94 (m, 2H), 7.42 (t, J=8.0 Hz, 1H), 7.04 (d,
[3.1.1]庚-2-亚基]肼基}-4-(4-氟苯基)噻唑(4h): 白色 J=8.6 Hz, 2H), 6.87 (s, 1H), 6.67 (d, J=8.7 Hz, 2H),
粉末，收率 82.3%，质量分数 99.5%。m. p. 236~237 ℃; 5.78 (d, J=11.9 Hz, 1H), 3.94 (dd, J=21.3、9.6 Hz, 1H),
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1
IR (KBr), v/cm : 3442, 3116, 1617, 1543; HNMR 2.95 (t, J=5.1 Hz, 1H), 2.91 (s, 6H), 2.53 (m, 1H),
(400 MHz, CDCl 3 )，δ: 7.65 (dd, J=8.7 Hz, 5.5 Hz, 2H), 2.09~1.96 (m, 2H), 1.77 (d, J=10.5 Hz, 1H), 1.59 (s,
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7.04 (d, J=8.6 Hz, 2H), 6.95 (t, J=8.8 Hz, 2H), 6.67 (d, 1H), 1.28 (d, J=5.7 Hz, 3H), 0.53 (s, 3H); CNMR
J=8.6 Hz, 2H), 6.65 (s, 1H), 5.77 (d, J=11.9 Hz, 1H), (100 MHz, CDCl 3 )，δ: 166.23, 165.30, 149.84, 149.39,
3.92 (dd, J=21.3、9.7 Hz, 1H), 2.94 (t, J=4.1 Hz, 1H), 148.46, 136.90, 131.95, 129.16, 127.87, 121.74, 120.85,
2.92 (s, 6H), 2.51 (m, 1H), 2.06~1.94 (m, 2H), 1.76 (d, 112.22, 103.90, 65.41, 45.77, 44.96, 41.14, 40.53, 26.48,
J=10.5 Hz, 1H), 1.44~1.39 (m, 1H), 1.28 (s, 3H), 0.52 23.38, 21.69; HRMS, m/Z: calcd for C 27 H 29 N 5 O 2 S
+
(s, 3H); 13 CNMR (100 MHz, CDCl 3 ), δ: 165.67, [M+H] : 488.2120; found: 488.2116。
165.11, 163.42, 160.97, 150.76, 127.99, 115.16, 114.95, 2-{2-[3-(4-二甲氨基亚苄基)-6,6-二甲基双环
112.30, 101.16, 65.33, 45.64, 44.92, 41.17, 40.61, [3.1.1]庚-2-亚基]肼基}-4-(2-氯苯基)噻唑(4l):白色粉
26.45, 23.42, 21.65; HRMS, m/Z: calcd for
+
C 27 H 29 FN 4 S [M+H] : 461.2175; found: 461.2179。 末，收率 81.4%，质量分数 98.1%。m. p. 224~225 ℃;
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1
IR (KBr), v/cm : 3429, 3149, 1617, 1549; HNMR
2-{2-[3-(4-二甲氨基亚苄基)-6,6-二甲基双环
(400 MHz, CDCl 3 )，δ: 7.69 (d, J=7.5 Hz, 1H), 7.33 (d,
[3.1.1]庚-2-亚基]肼基}-4-苯基噻唑(4i): 白色粉末，收
J=7.6 Hz, 1H), 7.18~7.07 (m, 3H), 7.02 (d, J=8.5 Hz,
率 75.6%，质量分数 96.2%。m. p. 203~204 ℃; IR (KBr), 2H), 6.66 (d, J=8.5 Hz, 2H), 5.77 (d, J= 11.9 Hz, 1H),
1
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v/cm : 3433, 3112, 1620, 1556; HNMR (400 MHz, 3.92 (dd, J=21.1、9.8 Hz, 1H), 2.96~ 2.92 (m, 1H),
CDCl 3 ), δ: 7.66 (d, J=7.3 Hz, 2H), 7.23 (d, J=6.3 Hz, 2.91 (s, 6H), 2.51 (m, 1H), 2.07~1.94 (m, 2H), 1.73 (d,
2H), 7.16 (t, J=7.3 Hz, 1H), 7.01 (d, J=8.6 Hz, 2H), J=6.1 Hz, 1H), 1.40 (dd, J=12.8、9.1 Hz, 1H), 1.26 (d,
6.70 (s, 1H), 6.63 (d, J=8.7 Hz, 2H), 5.76 (d, J=11.9 Hz, J=13.9 Hz, 3H), 0.52 (s, 3H); CNMR (100 MHz,
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1H), 3.89 (dd, J=21.3、9.6 Hz, 1H), 2.95~ 2.90 (m, 1H), CDCl 3 ), δ: 165.67, 164.13, 149.97, 148.18, 133.99,
2.89 (d, J=7.0 Hz, 6H), 2.48 (m, 1H), 2.04~1.91 (m, 131.75, 130.34, 128.15, 126.75, 124.22, 112.43, 107.36,