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。
                                                                                       +
                                                                                                     +
                                                 +
                                 +
            (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),
                                                                          +
                                                                                        +
                                                   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。
                         +
                                      +
            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,
                                                                    13
                                               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
                                                                                       +
                                                                                                     +
                                                        +
            39.8,36.5,33.7,21.0。HRMS (ESI),C 21 H 21 NO 4 Na ,  390.1312;测试值 390.1312。
                       +
            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,
                                                                                                     +
            C21H21NO4Na+,m/Z: [M+Na]+  理论值 374.1363;测          36.4 , 33.4 。 HRMS (ESI) , C 24H 21NO 4Na , m/Z:
                                                                     +
            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
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