Page 226 - 《精细化工》2021年第3期

·646· 精细化工 FINE CHEMICALS 第 38 卷

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(C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.57 (s, 1H, 5.48 (s, 2H, C11-H), 5.22 (s, 2H, C14-H), 5.12 (t, J =
C13-H), 7.32 (dt, J = 15.4、7.9 Hz, 2H, C19-H, 6.5 Hz, 1H, C6-H), 2.64~2.61 (m, 2H, C4-H),
C20-H), 7.27 (d, J = 6.1 Hz, 1H, C16-H), 7.15 (d, J = 2.15~2.11 (m, 2H, C5-H), 1.88 (s, 3H, C10-H), 1.66 (s,
13
3H, C9-H), 1.60 (s, 3H, C8-H); CNMR (151 MHz,
7.2 Hz, 1H, C18-H), 5.67 (s, 1H, C2-H), 5.49 (s, 2H, CDCl 3 ), δ: 165.86, 161.80, 144.08, 136.65, 132.26,
C11-H), 5.23 (s, 2H, C14-H), 5.05 (s, 1H, C6-H), 2.14 131.98, 131.06, 130.70, 126.62, 123.54, 123.52,
(d, J = 4.0 Hz, 7H, C4-H, C5-H, C10-H), 1.67 (s, 3H, 123.11, 115.51, 56.80, 53.40, 33.52, 26.74, 25.67,
C9-H), 1.59 (s, 3H, C8-H); 13 CNMR (151 MHz, +
CDCl 3 ), δ: 166.42, 161.35, 144.06, 136.33, 135.02, 25.43, 17.62。ESI-MS, m/Z: [M+H] 实测值 418.00；
132.54, 130.43, 129.02, 128.15, 126.15, 123.58, 理论值 418.11。
122.85, 114.90, 56.80, 53.45, 40.98, 25.89, 25.53, (E)-柠檬醛基间-溴苄基 1,2,3-三唑〔(E)-Ⅴl〕：
+
18.96, 17.62。ESI-MS, m/Z: [M+H] 实测值 374.02； 无色液体，产率 86.8%，HPLC 纯度：96.78%。IR
理论值 374.16。 (KBr)，ν/cm : 3128 (==C—H), 2964, 2908 (C—H),
–1
(Z)-柠檬醛基邻-溴苄基 1,2,3-三唑〔(Z)-Ⅴk〕： 1715 (C==O), 1643, 1485, 1435 (Ar, C==C), 1143 (C
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无色液体，产率 85.7%，HPLC 纯度：96.43%。IR —O); HNMR (600 MHz, CDCl 3 ), δ: 7.58 (s, 1H,
–1
(KBr)，ν/cm : 3157 (==C—H), 2974, 2927 (C—H), C13-H), 7.33~7.26 (m, 3H, C16-H, C18-H, C19-H),
1714 (C==O), 1644, 1570, 1441 (Ar, C==C), 1141 (C 7.16 (d, J = 7.2 Hz, 1H, C20-H), 5.68 (s, 1H, C2-H),
1
—O); HNMR (600 MHz, CDCl 3 ), δ: 7.65 (s, 1H, 5.50 (s, 2H, C11-H), 5.23 (s, 2H, C14-H), 5.05 (s, 1H,
C6-H), 2.15 (d, J = 5.5 Hz, 7H, C4-H, C5-H, C10-H),
C13-H), 7.63 (d, J = 8.0 Hz, 1H, C17-H), 7.32 (t, J = 1.67 (s, 3H, C9-H), 1.59 (s, 3H, C8-H); CNMR (151
13
7.5 Hz, 1H, C19-H), 7.24 (t, J = 7.0 Hz, 1H, C18-H), MHz, CDCl 3 ), δ: 166.41, 161.35, 144.01, 136.43,
7.18 (d, J = 7.6 Hz, 1H, C20-H), 5.67 (d, J = 5.8 Hz, 135.01, 132.59, 130.43, 129.01, 128.14, 126.14,
3H, C2-H, C11-H), 5.24 (s, 2H, C14-H), 5.14 (t, J = 123.59, 122.85, 114.90, 56.79, 53.44, 40.98, 25.98,
7.2 Hz, 1H, C5-H), 2.66~2.63 (m, 2H, C4-H), +
2.17~2.13 (m, 2H, C5-H), 1.89 (s, 3H, C10-H), 1.68 (s, 25.65, 18.96, 17.67。ESI-MS, m/Z: [M+H] 实测值
13
3H, C9-H), 1.61 (s, 3H, C8-H); CNMR (151 MHz, 417.99；理论值 418.11。
CDCl 3 ), δ: 165.85, 161.67, 143.74, 134.04, 133.24, (Z)-柠檬醛基对-溴苄基 1,2,3-三唑〔(Z)-Ⅴm〕：
132.24, 130.44, 130.38, 128.24, 123.81, 123.56, 无色液体，产率 87.5%，HPLC 纯度：98.31%。IR
123.49, 115.55, 56.83, 53.81, 33.52, 26.75, 25.67, –1
+
25.42, 17.63。ESI-MS, m/Z: [M+H] 实测值 417.98； (KBr)，ν/cm : 3140 (==C—H), 2965, 2930 (C—H),
1716 (C==O), 1644, 1550, 1493 (Ar, C==C), 1146 (C
理论值 418.11。 1
—O); HNMR (600 MHz, CDCl 3 ), δ: 7.54 (s, 1H,
(E)-柠檬醛基邻-溴苄基 1,2,3-三唑〔(E)-Ⅴk〕： C13-H), 7.52~7.50 (m, 2H, C17-H, C19-H), 7.16 (d, J
无色液体，产率 84.6%，HPLC 纯度：96.85%。IR = 8.4 Hz, 2H, C16-H, C20-H), 5.67 (s, 1H, C2-H),
–1
(KBr)，ν/cm : 3143 (==C—H), 2964, 2923 (C—H), 5.48 (s, 2H, C11-H), 5.22 (s, 2H, C14-H), 5.13 (t, J =
1712 (C==O), 1643, 1587, 1492 (Ar, C==C), 1135 7.2 Hz, 1H, C6-H), 2.65~2.62 (m, 2H, C4-H),
1
(C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.65 (s, 1H, 2.16~2.13 (m, 2H, C5-H), 1.89 (s, 3H, C10-H), 1.68 (s,
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C13-H), 7.61 (d, J = 8.0, 1H, C17-H), 7.31 (td, J = 3H, C9-H), 1.61 (s, 3H, C8-H); CNMR (151 MHz,
CDCl 3 ), δ: 165.85, 161.78, 144.05, 133.50, 132.32,
7.5、1.1 Hz, 1H, C19-H), 7.23 (td, J = 7.7、1.6 Hz, 1H,
132.27, 129.70, 123.53, 123.43, 122.99, 115.50, 56.79,
C18-H), 7.16 (dd, J = 7.6、1.5 Hz, 1H, C20-H), 5.68 (s, 53.48, 33.51, 26.74, 25.68, 25.43, 17.62。ESI-MS, m/Z:
1H, C2-H), 5.66 (s, 2H, C11-H), 5.23 (s, 2H, C14-H), [M+H] 实测值 417.99；理论值 418.11。
+
5.08~5.03 (m, 1H, C6-H), 2.14 (dd, J = 6.6、2.1 Hz, (E)-柠檬醛基对-溴苄基 1,2,3-三唑〔(E)-Ⅴm〕：
7H, C4-H, C5-H, C10-H), 1.67 (s, 3H, C9-H), 1.59 (s,
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3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ: 166.40, 无色液体，产率 86.5%，HPLC 纯度：96.67%。IR
–1
161.23, 143.68, 134.05, 133.23, 132.58, 130.44, (KBr)，ν/cm : 3136 (==C—H), 2965, 2929 (C—H),
130.39, 128.23, 123.85, 123.48, 122.87, 114.95, 56.83, 1716 (C==O), 1644, 1491, 1436 (Ar, C==C), 1146 (C
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53.81, 40.98, 25.99, 25.66, 18.97, 17.69。ESI-MS, m/Z: —O); HNMR (600 MHz, CDCl 3 ), δ: 7.55 (s, 1H,
+
[M+H] 实测值 418.00；理论值 418.11。 C13-H), 7.52~7.51 (m, 2H, C17-H, C19-H), 7.16 (d, J
(Z)-柠檬醛基间-溴苄基 1,2,3-三唑〔(Z)-Ⅴl〕： = 8.4 Hz, 2H, C16-H, C20-H), 5.68 (s, 1H, C2-H),
5.48 (s, 2H, C11-H), 5.23 (s, 2H, C14-H), 5.06 (t, J =
无色液体，产率 84.6%，HPLC 纯度：97.43%。IR 3.9 Hz, 1H, C6-H), 2.16 (dd, J = 5.3、2.1 Hz, 7H,
–1
(KBr)，ν/cm : 3144 (==C—H), 2967, 2928 (C—H), C4-H, C5-H, C10-H), 1.68 (s, 3H, C9-H), 1.60 (s, 3H,
1716 (C==O), 1648, 1577, 1438 (Ar, C==C), 1138 C8-H); CNMR (151 MHz, CDCl 3 ), δ: 166.42, 161.36,
13
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(C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.55 (s, 1H, 144.01, 133.51, 132.62, 132.32, 129.72, 123.46,
C13-H), 7.50~7.48 (m, 1H, C18-H), 7.43 (t, J = 1.6 Hz, 122.99, 122.84, 114.90, 56.79, 53.48, 40.99, 25.99,
+
1H, C16-H), 7.25 (dd, J = 15.8、8.0 Hz, 1H, C19-H), 25.66, 18.97, 17.69。ESI-MS, m/Z: [M+H] 实测值
7.19 (d, J = 8.0 Hz, 1H, C20-H), 5.66 (s, 1H, C2-H), 417.99；理论值 418.11。