Page 171 - 《精细化工》2020年第11期

第 11 期 张成龙，等: 诺蒎酮-噻唑腙类化合物的合成及其抑菌活性 ·2317·

4-(2-{2-[3-(4-氟亚苄基)-6,6-二甲基双环[3.1.1] 126.45 (C 24 ), 124.13 (C 13 , C 15 ), 116.83 (C 26 , C 28 ),
庚-2-亚基]肼基}噻唑-4-基)苯酚（Ⅲi）：黄色固体， 100.67 (C 22 ), 44.35 (C1), 42.36 (C 3 ), 39.43 (C 7 ), 31.85
1
产率 80.5%，m.p. 182.6~183.5 ℃。 HNMR (400 MHz, (C 4 ), 28.14 (C 2 ), 23.41 (Ar—CH 3 ), 21.68 (C 8 ), 21.42
+
(C 9 ); HRMS (ESI), m/Z: C 26 H 27 FN 3 S [M+H] 理论值
C 5 D 5 N), δ: 8.24 (d, J=8.6 Hz, 2H, C 12 —H, C 16 —H),
432.1912, 测试值 432.1917。
7.93 (s, 1H, C 22 —H), 7.71 (d, J=8.6 Hz, 2H, C 13 —H,
4-(2-{2-[6,6- 二甲基 -3-(4- 甲 基 亚苄基 ) 二环
C 15 —H), 7.43 (d, J=8.3 Hz, 2H, C 25 —H, C 29 —H),
[3.1.1]庚-2-亚基]肼基}噻唑-4-基)苯酚（Ⅲl）：黄色
7.26 (d, J=8.1 Hz, 2H, C 26 —H, C 28 —H), 7.14 (s, 1H, 1
C 10 —H), 3.23~3.04 (m, 2H, C 1 —H, C 3 —H), 2.87 (m, 固体，产率 73.5%，m.p. 161.3~161.9 ℃。 HNMR
1H, C 4—H), 2.65 (m, 2H, C 2—H), 2.17 (m, 1H, C 4—H), (400 MHz, C 5 D 5 N), δ: 8.22 (d, J=8.6 Hz, 2H, C 12 —H,
13
1.49 (s, 3H, C 8 —H), 0.99 (s, 3H, C 9 —H); CNMR C 16 —H), 8.06 (s, 1H, C 22 —H), 7.69 (d, J=8.3 Hz, 2H,
(100 MHz, C 5 D 5 N), δ: 171.36 (C 19 ), 163.47 (C 14 ), C 13—H, C 15 —H), 7.40 (t, J=7.9 Hz, 4H, C 25—H, C 26 —H,
161.27 (C 27 ), 159.21 (C 6 ), 155.32 (C 21 ), 152.25 (C 5 ), C 28 —H, C 29 —H), 7.21 (s, 1H, C 10 —H), 3.12~2.94 (m,
134.70 (C 10 ), 132.65 (C 11 ), 128.01 (C 12 , C 16 ), 126,67 2H, C 1 —H, C 3 —H), 2.59 (m, 1H, C 4 —H), 2.39 (s, 3H,
(C 24 , C 25 , C 29 ), 117.02 (C 26 , C 28 ), 115.68 (C 13 , C 15 ),
101.44 (C 22 ), 41.69 (C 1 ), 40.38 (C 3 ), 35.24 (C 7 ), 32.54 Ar—CH 3), 2.18 (m, 2H, C 2—H), 1.39 (m, 1H, C 4—H),
13
(C 4 ), 28.76 (C 2 ), 21.35 (C 8 ), 21.09 (C 9 ); HRMS (ESI), 1.37 (s, 3H, C 8 —H), 0.98 (s, 3H, C 9 —H); CNMR
+
m/Z: C 25 H 25 FN 3 OS [M+H] 理论值 434.1548, 测试值 (100 MHz, C 5 D 5 N), δ: 170.77 (C 19 ), 158.57 (C 27 ),
434.1546。 154.91 (C 6 ), 151.72 (C 21 ), 131.45 (C 14 ), 131.19
(C 5 ),130.78 (C 11 ), 130.09 (C 10 ), 129.34 (C 12 , C 16 ),
2-{2- [6,6-二甲基-3-(4-甲基亚苄基)二环[3.1.1]
127.78 (C 13 , C 15 ), 127.32 (C 25 , C 29 ), 127.15 (C 24 ),
庚-2-亚基]肼基}-4-苯基噻唑（Ⅲj）：黄色固体，产 116.21 (C 26 , C 28 ), 100.62 (C 22 ), 42.69 (C 1 ), 40.98 (C 3 ),
1
率 84.3%，m.p. 163.6~164.6 ℃。 HNMR (400 MHz, 39.24 (C 7 ), 32.14 (C 4 ), 28.21 (C 2 ), 21.35 (Ar—CH 3 ),
CDCl 3), δ: 12.48 (s, 1H, N—H), 7.63 (d, J=7.1 Hz, 2H, 20.95 (C 8), 19.89 (C 9); HRMS (ESI), m/Z: C 26H 28N 3OS
+
C 12 —H, C 16 —H), 7.42 (s, 1H, C 22 —H), 7.39~7.28 (m, [M+H] 理论值 430.1941, 测试值 430.1935。
5H, C 25 —H, C 26 —H, C 27 —H, C 28 —H, C 29 —H), 7.12 2-{2-[3-(4- 氯 亚苄基 )-6,6- 二甲基双环 [3.1.1]
(d, J=7.1 Hz, 2H, C 13—H, C 15—H), 6.67 (s, 1H, C 10 —H), 庚-2-亚基]肼基}-4-苯基噻唑（Ⅲm）：黄色固体，产
1
3.06~2.93 (m, 2H, C 1—H, C 3—H), 2.45 (m, 1H, C 4—H), 率 77.8%，m.p. 185.6~186.6 ℃。 HNMR (400 MHz,
2.28 (s, 3H, Ar—CH 3 ), 2.14 (m, 2H, C 2 —H), 1.41 (m, CDCl 3), δ: 12.56 (s, 1H, N—H), 7.63 (d, J=6.9 Hz, 2H,
13
1H, C 4 —H), 0.85 (s, 6H, C 8 —H, C 9 —H); CNMR C 12 —H, C 16 —H), 7.42~7.31 (m, 6H, C 22 —H, C 25 —H,
(100 MHz, CDCl 3 ), δ: 169.23 (C 19 ), 165.78 (C 6 ), C 26 —H, C 27 —H, C 28 —H, C 29 —H), 7.00 (d, J=7.1 Hz,
140.32 (C 21 ), 138.09 (C 5 ), 133.35 (C 14 ), 130.74 (C 24 ), 2H, C 13 —H, C 15 —H), 6.63 (s, 1H, C 10 —H), 3.04~2.91
130.13 (C 11 ), 129.97 (C 10 ), 129.48 (C 12 , C 16 ), 129.40 (m, 2H, C 1—H, C 3—H), 2.81 (m, 1H, C 4—H), 2.14 (m,
(C 13 , C 15 ), 129.05 (C 25 , C 29 ), 127.25 (C 26 , C 28 ), 125.34
(C 27 ), 100.68 (C 22 ) , 44.27 (C 1 ), 42.06 (C 3 ), 39.23 (C 7 ), 2H, C 2 —H), 1.41 (m, 1H, C 4 —H), 0.85 (s, 6H, C 8 —H,
13
31.87 (C 4 ), 28.24 (C 2 ), 24.41 (Ar—CH 3 ), 21.98 (C 9 ), C 9 —H); CNMR (100 MHz, CDCl 3 ), δ: 169.95 (C 19 ),
+
21.20 (C 9 ); HRMS (ESI), m/Z: C 26 H 28 N 3 S [M+H] 理 165.65 (C 6 ), 140.86 (C 21 ), 135.09 (C 5 ), 134.32 (C 14 ),
131.59 (C 11 ), 130.67 (C 10 ), 129.88 (C 24 ), 129.85 (C 12 ,
论值 414.2002, 测试值 414.2003。 C 16 ), 128.99 (C 13 , C 15 ), 127.67 (C 25 , C 29 ), 125.89 (C 26 ,
2-{2-[6,6-二甲基-3-(4-甲基亚苄基)二环[3.1.1] C 28 ),125.47 (C 27 ), 101.28 (C 22 ), 44.75 (C 1 ), 42.60 (C 3 ),
庚-2-亚基]肼基}-4-(4-氟苯基)噻唑（Ⅲk）：黄色固 39.61 (C 7 ), 32.07 (C 4 ), 28.15 (C 2 ), 21.92 (C 9 ), 21.40
+
1
体，产率 78.9%，m.p. 177.6~178.5 ℃。 HNMR (C 9 ); HRMS (ESI), m/Z: C 25 H 25 ClN 3 S [M+H] 理论值
434.1521, 测试值 434.1538。
(400 MHz, CDCl 3 ), δ: 12.48 (s, 1H, N—H), 7.61 (d,
2-{2-[3-(4- 氯 亚苄基 )-6,6- 二甲基双环 [3.1.1]
J=6.8 Hz, 2H, C 12 —H, C 16 —H), 7.42 (s, 1H, C 22 —H),
庚-2-亚基]肼基}-4-(4-氟苯基)噻唑（Ⅲn）：黄色固
7.39 (d, J=7.9 Hz, 2H, C 25 —H, C 29 —H), 7.20 (d,
1
体，产率 75.9%，m.p. 199.2~200.3 ℃。 HNMR
J=6.8 Hz, 2H, C 13—H, C 15—H), 7.12 (d, J=7.9 Hz, 2H,
(400 MHz, CDCl 3 ), δ: 12.40 (s, 1H, N—H), 7.64 (d,
C 26 —H, C 28 —H), 6.66 (s, 1H, C 10 —H), 3.03~2.90 (m,
J=8.8 Hz, 2H, C 12 —H, C 16 —H), 7.40 (s, 1H, C 22 —H),
2H, C 1 —H, C 3 —H), 2.74 (m, 1H, C 4 —H), 2.28 (s, 3H,
7.32 (d, J=9.0 Hz, 2H, C 25 —H, C 29 —H), 7.05 (d,
Ar—CH 3), 2.12 (m, 2H, C 2—H), 1.39 (m, 1H, C 4—H),
13
0.86 (s, 6H, C 8 —H, C 9 —H); CNMR (100 MHz, J=9.0 Hz, 2H, C 13 —H, C 15 —H), 6.93 (d, J=8.8 Hz, 2H,
CDCl 3 ), δ: 169.32 (C 19 ), 165.84 (C 27 ), 163.70 (C 6 ), C 26 —H, C 28 —H), 6.50 (s, 1H, C 10 —H), 3.04~2.92 (m,
139.95 (C 21 ), 138.33 (C 14 ), 133.58 (C 5 ), 130.96 (C 11 ), 2H, C 1 —H, C 3 —H), 2.74 (m, 1H, C 4 —H), 2.47 (m,
130.14 (C 10 ), 129.70 (C 25 , C 29 ), 127.81 (C 12 , C 16 ), 2H, C 2 —H), 1.19 (m, 1H, C 4 —H), 0.78 (s, 6H, C 8 —H,