Page 150 - 《精细化工》2023年第1期
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·142· 精细化工 FINE CHEMICALS 第 40 卷
3H) , 3.20~3.13 (m , 1H) , 2.63~2.53 (m , 2H) , (s,3H),2.21~2.11(m,1H),2.05~1.97 (m,1H)。
13
2.15~2.00 (m,2H)。 CNMR (100 MHz,CDCl 3),δ: 13 CNMR (100 MHz , CDCl 3) , δ: 172.4 , 168.1 ,
171.9,168.2,141.0,133.9,132.5,132.0,128.8, 140.7,136.0,133.8,132.0,130.7,126.4,126.3,
128.7,123.1,51.6,41.8,39.6,36.3,33.7。HRMS 125.4,123.1,51.6,41.2,36.4,34.8,33.4,19.6。
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(ESI) , C 20H 18ClNO 4Na , m/Z: [M+Na] 理论值 HRMS (ESI),C 21H 21NO 4Na ,m/Z: [M+Na] 理论值
394.0817;测试值 394.0816。 374.1363;测试值 374.1363。
5-邻苯二甲酰亚胺基-3-对氟苯基戊酸甲酯(Ⅲc): 5-邻苯二甲酰亚胺基-3-对甲氧苯基戊酸甲酯(Ⅲ
1
1
黄色黏稠液体,产率 96%。 HNMR (400 MHz, g):白色黏稠液体,产率 97%。 HNMR (400 MHz,
CDCl 3),δ: 7.78~7.75 (m,2H),7.69~7.67 (m,2H), CDCl 3),δ: 7.78~7.76 (m,2H),7.68~7.66 (m,2H),
7.21~7.18 (m,2H),6.92 (t,J = 8.0 Hz,2H), 7.13 (d,J = 6.0 Hz,2H),6.76 (d,J = 6.0 Hz,
3.64~3.55 (m,2H),3.52 (s,3H),3.22~3.14 (m, 2H),3.71(s,3H),3.62~3.53 (m,5H),3.15~3.12
1H) , 2.67~2.62 (m , 1H) , 2.58~2.52 (m , 1H) 。 (m,1H),2.65~2.51 (m,2H),2.15~1.96 (m,2H)。
13 13
CNMR (100 MHz,CDCl 3),δ: 172.0,168.2,161.6 CNMR (100 MHz , CDCl 3) , δ: 172.3 , 168.3 ,
(d,J FC = 244.0 Hz),138.1 (d,J FC = 3.0 Hz),133.9, 158.3,134.4,133.8,132.1,128.3,123.0,113.9,
132.0,128.9 (d,J FC = 8.0 Hz),123.1,115.4 (d,J FC = 55.1,51.6,42.2,39.4,36.5,33.8。HRMS (ESI),
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19
22.0 Hz),51.6,41.9,39.4,36.3,33.9。 FNMR C 21H 21NO 5Na ,m/Z∶[M+Na] 理论值 390.1312;测
(376 MHz , CDCl 3) , δ: 115.86 。 HRMS (ESI) , 试值 390.1311。
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C 20H 18FNO 4Na ,m/Z: [M+Na] 理论值 378.1112; 测 5-邻苯二甲酰亚胺基-3-邻甲氧苯基戊酸甲酯(Ⅲh):
1
试值 378.1112。 白色黏稠液体,产率 95%。 HNMR (400 MHz,
5-邻苯二甲酰亚胺基-3-对甲苯基戊酸甲酯(Ⅲd): CDCl 3),δ: 7.78~7.76 (m,2H),7.68~7.66 (m,2H),
1
白色黏稠液体,产率 98%。 HNMR (400 MHz, 7.18 (d,J = 8.0 Hz, 1H),7.11 (t,J = 8.0 Hz,
CDCl 3),δ: 7.77~7.74 (m,2H),7.67~7.65 (m,2H), 1H),6.86 (t,J = 8.0 Hz,1H),6.79 (d,J = 8.0 Hz,
7.10 (d,J = 8.0 Hz,2H),7.02 (d,J = 8.0 Hz, 1H),3.79 (s,3H),3.62~3.54 (m,6H),2.68 (d,J =
2H),3.62~3.58 (m,2H),3.56 (s,3H),3.18~3.11 8.0 Hz,2H),2.28~2.19 (m,1H),2.06~1.98 (m,
(m , 1H) , 2.66~2.53 (m , 2H) , 2.16 (s , 3H) , 1H)。 CNMR (100 MHz,CDCl 3),δ: 172.8,168.2,
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13
2.14~2.08 (m,1H),2.05~1.97 (m,1H)。 CNMR (100 157.3,133.7,132.2,130.2,128.3,127.7,123.0,
MHz ,CDCl 3) ,δ: 172.3 ,168.2 ,139.4 , 136.2 , 120.6,110.7,55.3,51.5,39.7,36.6,34.5,32.1。
133.7,132.1,129.3,127.2,123.0,51.5,42.0, HRMS (ESI),C 21H 21NO 5Na ,m/Z: [M+Na] 理论值
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39.8,36.5,33.7,21.0。HRMS (ESI),C 21 H 21 NO 4 Na , 390.1312;测试值 390.1312。
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m/Z: [M+Na] 理论值 374.1363;测试值 374.1363。 5-邻苯二甲酰亚胺基-3-萘基戊酸甲酯(Ⅲi):白
5-邻苯二甲酰亚胺基-3-间甲苯基戊酸甲酯(Ⅲe): 色黏稠液体,产率 95%。 HNMR (400 MHz,CDCl 3),
1
白色黏稠液体,产率 97%。1HNMR (400 MHz,CDCl3), δ: 8.17~8.15 (d,J = 8.0 Hz,1H),7.78 (d,J = 8.0
δ: 7.76~7.74 (m,2H),7.67~7.64 (m,2H),7.09 (t,J = Hz,1H),7.73~7.69 (m,2H),7.66~7.61 (m,3H),
8.0 Hz,1H),7.01 (s,2H),6.86 (d,J = 8.0 Hz,1H), 7.53~7.40 (m,4H),4.17 (s,1H),3.70~3.58 (m,
3.62~3.57 (m,5H),3.18~3.11 (m,1H),2.66~2.54 (m, 2H),3.56 (s,3H),2.77 (d,J = 8.0 Hz,2H),
2H),2.25 (s,3H),2.19~2.10 (m,1H),2.05~1.97 (m, 2.35~2.33 (m,1H),2.24~2.16 (m,1H)。 CNMR
13
1H)。13CNMR (100 MHz,CDCl3),δ: 172.3,168.2, (100 MHz,CDCl 3),δ: 172.4,168.1,138.6,134.2,
142.5,138.0,133.7,132.0,128.5,128.1,127.4,124.4, 134.1,134.0,133.8,132.0,131.5,129.0,127.3,
123.0,51.6,41.9,40.1,36.5,33.6,21.4。HRMS (ESI), 126.2,125.6,123.5,123.0,122.9,51.7,41.5,
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C21H21NO4Na+,m/Z: [M+Na]+ 理论值 374.1363;测 36.4 , 33.4 。 HRMS (ESI) , C 24H 21NO 4Na , m/Z:
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试值 374.1364。 [M+Na] 理论值 410.1363;测试值 410.1362。
5-邻苯二甲酰亚胺基-3-邻甲苯基戊酸甲酯(Ⅲf): 1.2.3 5-邻苯二甲酰亚胺基-3-对氯苯基戊酸(Ⅳ)
1
白色黏稠液体,产率 95%。 HNMR (400 MHz, 的合成。
CDCl 3),δ: 7.77~7.75 (m,2H),7.67~7.65 (m,2H), 向 25.0 mL 单口圆底烧瓶中,分别加入 5-邻苯二甲
7.20 (d,J = 12.0 Hz,1H),7.12~7.06 (m,2H), 酰亚胺基-3-对氯苯基戊酸甲酯 Ⅲb 1.59 g (4.3 mmol)
7.00~6.97 (m,1H),3.65~3.61 (m,1H),3.58 (s, 和 10.0 mL 浓盐酸(6 mol/L),在 80 ℃下反应 8 h。
3H),3.55~3.48 (m,2H),2.66~2.52 (m,2H),2.36 待反应冷却后,过滤,得到 1.41 g 白色固体,即为产