Page 224 - 《精细化工》2021年第3期

·644· 精细化工 FINE CHEMICALS 第 38 卷

1716 (C==O), 1646, 1520, 1442 (Ar, C==C), 1155 (C 7H, C4-H, C5-H, C10-H), 1.66 (s, 3H, C9-H), 1.58 (s,
13
1
—O); HNMR (600 MHz, CDCl 3 ), δ: 7.49 (s, 1H, 3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ: 166.43,
C13-H), 7.17 (s, 4H, Ar-H), 5.65 (s, 1H, C2-H), 5.46 161.22, 160.13, 143.79, 135.93, 132.59, 130.21,
(s, 2H, C11-H), 5.19 (s, 2H, C14-H), 5.13~5.10 (m, 123.48, 122.87, 120.31, 114.96, 114.29, 113.71, 56.85,
1H, C6-H), 2.63~2.60 (m, 2H, C4-H), 2.35 (s, 3H, 55.30, 54.14, 40.98, 25.99, 25.65, 18.95, 17.68。
C21-H), 2.13 (d, J = 7.6 Hz, 2H, C5-H), 1.87 (d, J = ESI-MS, m/Z: [M+H] 实测值 370.06；理论值 370.21。
+
1.4 Hz, 3H, C10-H), 1.67 (d, J = 1.0 Hz, 3H, C9-H), (Z)-柠檬醛基对-甲氧基苄基 1,2,3-三唑〔(Z)-
13
1.59 (s, 3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ:
165.85, 161.59, 143.72, 138.74, 132.23, 131.43, Ⅴ f〕：无色液体，产率 87.3%，HPLC 纯度：97.65%。
–1
129.79, 128.18, 123.56, 123.30, 115.58, 56.85, 53.87, IR (KBr)，ν/cm : 3143 (==C—H), 2972, 2913 (C—H),
33.49, 26.70, 25.67, 25.41, 21.15, 17.56。ESI-MS, m/Z: 1718 (C==O), 1642, 1512, 1438 (Ar, C==C), 1152
1
+
[M+H] 实测值 354.07；理论值 354.21。 (C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.49 (s, 1H,
(E)-柠檬醛基对-甲基苄基 1,2,3-三唑〔(E)-Ⅴd〕： C13-H), 7.26~7.20 (m, 2H, C16-H, C20-H), 6.93~6.87
(m, 2H, C17-H, C19-H), 5.67~5.64 (m, 1H, C2-H),
无色液体，产率 81.8%，HPLC 纯度：96.87%。IR 5.45 (s, 2H, C11-H), 5.20 (s, 2H, C14-H), 5.16~5.10
–1
(KBr)，ν/cm : 3140 (==C—H), 2967, 2924 (C—H), (m, 1H, C6-H), 3.81 (s, 3H, C21-H), 2.63 (dd, J = 9.3、
1714 (C==O), 1649, 1514, 1442 (Ar, C==C), 1135 6.4 Hz, 2H, C4-H), 2.14 (dt, J = 15.6、4.7 Hz, 2H,
1
(C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.50 (s, 1H, C5-H), 1.88 (d, J = 1.4 Hz, 3H, C10-H), 1.68 (d, J =
C13-H), 7.17 (s, 4H, Ar-H), 5.65 (s, 1H, C2-H), 5.46 1.0 Hz, 3H, C9-H), 1.61 (s, 3H, C8-H); CNMR (151
13
(s, 2H, C11-H), 5.20 (s, 2H, C14-H), 5.07~5.02 (m, MHz, CDCl 3 ), δ: 165.85, 161.60, 159.94, 143.65,
1H, C6-H), 2.34 (s, 3H, C21-H), 2.13 (dd, J = 5.6、2.1 132.19, 129.71, 126.43, 123.55, 123.18, 115.50,
Hz, 7H, C4-H, C5-H, C10-H), 1.66 (s, 3H, C9-H), 114.49, 56.85, 55.33, 53.74, 33.49, 26.73, 26.68, 25.66,
13
1.58 (s, 3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ: 17.61。ESI-MS, m/Z: [M+H] 实测值 370.06；理论值
+
166.41, 161.15, 143.71, 138.64, 132.54, 131.45, 370.21。
129.78, 128.19, 123.33, 122.87, 114.98, 56.85, 54.05,
40.97, 25.99, 25.65, 21.28, 18.94, 17.64。ESI-MS, m/Z: (E)-柠檬醛基对-甲氧基苄基 1,2,3-三唑〔(E)-
+
[M+H] 实测值 354.07；理论值 354.21。 Ⅴ f〕：无色液体，产率 86.7%，HPLC 纯度：98.58%。
–1
(Z)-柠檬醛基间-甲氧基苄基 1,2,3-三唑〔(Z)-Ⅴe〕： IR (KBr)，ν/cm : 3142 (==C—H), 2963, 2932 (C—H),
1718 (C==O), 1646, 1612, 1516 (Ar, C==C), 1135
无色液体，产率 85.4%，HPLC 纯度：98.63%。IR 1
–1
(KBr)，ν/cm : 3111，3067 (==C—H), 2978, 2964 (C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.50 (s, 1H,
C13-H), 7.25~7.22 (m, 2H, C16-H, C20-H), 6.92~6.87
(C—H), 1707 (C==O), 1642, 1586, 1458 (Ar, C==C), (m, 2H, C17-H, C19-H), 5.66 (s, 1H, C2-H), 5.44 (s,
1
1138 (C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.59 (s, 2H, C11-H), 5.20 (d, J = 4.7 Hz, 2H, C14-H), 5.05 (dd,
1H, C13-H), 7.38~7.33 (m, 1H, C19-H), 7.22 (dd, J = J = 4.7、3.3 Hz, 1H, C6-H), 3.83~3.78 (m, 3H, C21-H),
7.4、1.2 Hz, 1H, C20-H), 6.95 (dd, J = 17.4、7.9 Hz, 2.14 (dd, J = 5.5、1.8 Hz, 7H, C4-H, C5-H, C10-H),
2H, C16-H, C18-H), 5.67 (s, 1H, C2-H), 5.54 (s, 2H, 1.67 (s, 3H, C9-H), 1.58 (s, 3H, C8-H); CNMR (151
13
C11-H), 5.21 (s, 2H, C14-H), 5.16~5.11 (m, 1H, MHz, CDCl 3 ), δ: 166.41, 161.16, 159.96, 143.64,
C6-H), 3.88 (s, 3H, C21-H), 2.66~2.61 (m, 2H, C4-H), 132.61, 129.72, 126.45, 123.28, 122.87, 114.97,
2.15 (dd, J = 15.3、7.5 Hz, 2H, C5-H), 1.88 (d, J = 1.2 114.48, 56.85, 55.32, 53.73, 40.96, 25.98, 25.65, 18.94,
Hz, 3H, C10-H), 1.68 (s, 3H, C9-H), 1.61 (s, 3H, 17.63。ESI-MS, m/Z: [M+H] 实测值 370.06；理论值
+
13
C8-H); CNMR (151 MHz, CDCl 3 ), δ: 165.85, 161.44, 370.21。
157.05, 143.30, 132.23, 130.40, 123.76, 123.62,
122.85, 120.95, 115.65, 110.77, 56.95, 55.46, 49.15, (Z)-柠檬醛基邻-氟苄基 1,2,3-三唑〔(Z)- gⅤ 〕：
33.42, 26.75, 25.71, 25.40, 17.57 。 ESI-MS, m/Z: 无色液体，产率 84.5%，HPLC 纯度：97.75%。IR
–1
+
[M+H] 实测值 370.06；理论值 370.21。 (KBr)，ν/cm : 3145 (==C—H), 2963, 2917 (C—H),
(E)-柠檬醛基间-甲氧基苄基 1,2,3-三唑〔(E)-Ⅴe〕： 1716 (C==O), 1645, 1577, 1444 (Ar, C==C), 1140 (C
1
—O); HNMR (600 MHz, CDCl 3 ), δ: 7.61 (s, 1H,
无色液体，产率 86.5%，HPLC 纯度：98.78%。IR
–1
(KBr)，ν/cm : 3143 (==C—H), 2966, 2919 (C—H), C13-H), 7.37~7.33 (m, 1H, C19-H), 7.28 (d, J = 5.7
Hz, 1H, C18-H), 7.13 (dd, J = 17.2、8.3 Hz, 2H,
1712 (C==O), 1647, 1600, 1491 (Ar, C==C), 1138 C17-H, C20-H), 5.65 (s, 1H, C2-H), 5.57 (s, 2H,
1
(C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.53 (s, 1H,
C11-H), 5.21 (d, J = 4.0 Hz, 2H, C14-H), 5.12 (t, J =
C13-H), 7.28 (dd, J = 12.9、5.0 Hz, 1H, C19-H), 7.9 Hz, 1H, C6-H), 2.63 (d, J = 7.6 Hz, 2H, C4-H),
6.90~6.83 (m, 2H, C18-H, C20-H), 6.79 (s, 1H, 2.14 (t, J = 7.1 Hz, C5-H), 1.87 (d, J = 1.3 Hz, 3H,
C16-H), 5.66 (d, J = 0.4 Hz, 1H, C2-H), 5.47 (s, 2H, C10-H), 1.66 (s, 3H, C9-H), 1.59 (s, 3H, C8-H);
C11-H), 5.21 (s, 2H, C14-H), 5.07~5.02 (m, 1H, 13 CNMR (151 MHz, CDCl 3 ), δ: 165.83, 161.66,
C6-H), 3.78 (s, 3H, C21-H), 2.13 (dd, J = 5.6、2.1 Hz, 161.36, 159.72, 143.81, 132.23, 130.98, 130.61,