Page 223 - 《精细化工》2021年第3期

第 3 期 何 云，等: 柠檬醛基 1,2,3-三唑类化合物的合成及其抑菌活性 ·643·

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P 为用供试化合物处理后的平均菌丝扩展直径，mm。 25.41, 18.98, 17.62。ESI-MS, m/Z: [M+H] 实测值
354.07；理论值 354.21。
2 结果与讨论 (E)-柠檬醛基邻-甲基苄基 1,2,3-三唑〔(E)-Ⅴb〕：

无色液体，产率 82.6%，HPLC 纯度：97.48%。IR
2.1 目标产物的结构表征
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(KBr)，ν/cm : 3144 (==C—H), 2967, 2926 (C—H),
(Z)-柠檬醛基苄基 1,2,3-三唑〔(Z)-Ⅴa〕：无色
1716 (C==O), 1644, 1497, 1440 (Ar, C==C), 1138
液体，产率 83.5%，HPLC 纯度：98.45%。IR (KBr)， (C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.42 (s, 1H,
1
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ν/cm : 3142 (==C—H), 2969, 2921 (C—H), 1717 C13-H), 7.28 (d, J = 4.5 Hz, 1H, C20-H), 7.24~7.20
(C==O), 1646, 1498, 1453 (Ar, C==C), 1155 (C—O); (m, 2H, C17-H, C19-H), 7.17~7.15 (m, 1H, C18-H),
1 HNMR (600 MHz, CDCl 3 )，δ: 7.53 (s, 1H, C13-H), 5.66 (d, J = 0.9 Hz, 1H, C2-H), 5.53 (s, 2H, C11-H),
5.20 (d, J = 5.3 Hz, 2H, C14-H), 5.08~5.02 (m, 1H,
7.36 (dd, J = 6.9、1.9 Hz, 3H, C16-H, C18-H, C20-H), C6-H), 2.28 (s, 3H, C21-H), 2.14 (t, J = 2.3 Hz, 7H,
7.26 (d, J = 6.9 Hz, 2H, C17-H, C19-H), 5.65 (s, 1H, C4-H, C5-H, C10-H), 1.67 (s, 3H, C9-H), 1.58 (s, 3H,
C2-H), 5.51 (s, 2H, C11-H), 5.20 (d, J = 1.4 Hz, 2H, C8-H); CNMR (151 MHz, CDCl 3 ), δ: 166.40, 161.15,
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C14-H), 5.11 (dd, J = 10.2、4.0 Hz, 1H, C6-H), 2.62 (t, 143.58, 136.97, 132.54, 132.37, 131.05, 129.42,
J = 7.8 Hz, 2H, C4-H), 2.14 (d, J = 9.1、4.8 Hz, 2H, 129.19, 126.68, 123.17, 122.87, 114.93, 56.85, 52.35,
C5-H), 1.87 (s, 3H, C10-H), 1.66 (s, 3H, C9-H), 1.59 40.97, 25.99, 25.65, 18.99, 18.94,17.68。ESI-MS, m/Z:
13
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(s, 3H, C8-H); CNMR (151 MHz, CDCl 3 )，δ: 165.82, [M+H] 实测值 354.06；理论值 354.21。
161.63, 143.77, 134.49, 132.20, 129.11, 128.77, (Z)-柠檬醛基间-甲基苄基 1,2,3-三唑〔(Z)-Ⅴc〕：
128.10, 123.55, 123.46, 115.55, 56.82, 54.15, 33.48, 无色液体，产率 83.4%，HPLC 纯度：95.74%。IR
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26.73, 25.66, 25.39, 17.61。ESI-MS，m/Z: [M+H] 实
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(KBr)，ν/cm : 3142 (==C—H), 2969, 2918 (C—H),
测值 340.05；理论值 340.19。
1718 (C==O), 1646, 1502, 1442 (Ar, C==C)，1153
(E)-柠檬醛基苄基 1,2,3-三唑〔(E)-Ⅴa〕：无色
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(C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.53 (s, 1H,
液体，产率 82.2%，HPLC 纯度：98.66%。IR (KBr)， C13-H), 7.27 (m, 1H, C19-H), 7.17 (d, J = 7.6 Hz, 1H,
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ν/cm : 3140 (==C—H), 2967, 2922 (C—H), 1718 C20-H), 7.10~7.07 (m, 2H, C16-H, C18-H), 5.67 (d,
(C==O), 1647, 1498, 1445 (Ar, C==C), 1155(C—O); J = 0.6 Hz, 1H, C2-H), 5.48 (s, 2H, C11-H), 5.22 (s,
1 2H, C14-H), 5.15~5.11 (m, 1H, C6-H), 2.65~2.62 (m,
HNMR (600 MHz, CDCl 3 ), δ: 7.55 (s, 1H, C13-H),
7.38 (ddd, J = 6.8、4.1、1.4 Hz, 3H, C16-H, C18-H, 2H, C4-H), 2.35 (s, 3H, C21-H), 2.17~2.12 (m, 2H,
C20-H), 7.30~7.28 (m, 2H, C17-H, C19-H), 5.67 (s, C5-H), 1.88 (s, 3H, C10-H), 1.68 (s, 3H, C9-H), 1.61
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(s, 3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ: 165.87,
1H, C2-H), 5.53 (s, 2H, C11-H), 5.22 (d, J = 2.7 Hz, 161.65, 143.76, 139.00, 134.35, 132.25, 129.56,
2H, C14-H), 5.08~5.03 (m, 1H, C6-H), 2.16~2.14 (m, 129.01, 128.87, 125.21, 123.55, 123.41, 115.57, 56.87,
7H, C4-H, C5-H, C10-H), 1.68 (s, 3H, C9-H), 1.59 (s,
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3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ: 166.43, 54.21, 33.50, 26.74, 25.68, 25.43, 21.33, 17.62。
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161.22, 143.78, 134.47, 132.59, 129.14, 128.81, ESI-MS, m/Z: [M+H] 实测值 354.07；理论值 354.21。
128.13, 123.46, 122.87, 114.95, 56.85, 54.20, 40.98, (E)-柠檬醛基间-甲基苄基 1,2,3-三唑〔(E)-Ⅴc〕：
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25.99, 25.66, 18.95, 17.68。ESI-MS, m/Z: [M+H] 实 无色液体，产率 82.7%，HPLC 纯度：96.88%。IR
测值 340.05；理论值 340.19。 (KBr)，ν/cm : 3140 (==C—H), 2964, 2925 (C—H),
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(Z)-柠檬醛基邻-甲基苄基 1,2,3-三唑〔(Z)-Ⅴb〕： 1715 (C==O), 1644, 1498, 1435 (Ar, C==C)，1138
无色液体，产率 84.3%，HPLC 纯度：99.05%。IR (C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.54 (s, 1H,
1
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(KBr)，ν/cm : 3036 (==C—H), 2970, 2917 (C—H), C13-H), 7.29~7.25 (m, 1H, C19-H), 7.17 (d, J = 7.6
1717 (C==O), 1646, 1497, 1456 (Ar, C==C), 1155 Hz, 1H, C20-H), 7.10~7.07 (m, 2H, C16-H, C18-H),
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(C—O); HNMR (600 MHz, CDCl 3 ), δ: 7.40 (s, 1H, 5.68 (s, 1H, C2-H), 5.48 (s, 2H, C11-H), 5.22 (d, J =
2.4 Hz, 2H, C14-H), 5.08~5.03 (m, 1H, C6-H), 2.35 (s,
C13-H), 7.29 (d, J = 7.5 、 1.3 Hz, 1H, C20-H), 3H, C21-H), 2.16~2.14 (m, 7H, C4-H, C5-H, C10-H),
7.23~7.20 (m, 2H, C17-H, C19-H), 7.17~7.14 (m, 1H, 1.68 (s, 3H, C9-H), 1.59 (s, 3H, C8-H); CNMR (151
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C18-H), 5.66~5.64 (m, 1H, C2-H), 5.52 (s, 2H, MHz, CDCl 3 ), δ: 166.43, 161.19, 143.69, 138.99,
C11-H), 5.19 (s, 2H, C14-H), 5.14~5.09 (m, 1H, 134.37, 132.54, 129.55, 129.00, 128.86, 125.21,
C6-H), 2.61 (dd, J = 9.3、6.4 Hz, 2H, C4-H), 2.28 (s, 123.45, 122.87, 114.97, 56.86, 54.20, 40.97, 25.99,
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3H, C21-H), 2.13 (dt, J = 15.3、5.3 Hz, 2H, C5-H), 25.65, 21.31, 18.95, 17.68。ESI-MS, m/Z: [M+H] 实
1.87 (d, J = 1.3 Hz, 3H, C10-H), 1.67 (d, J = 1.0 Hz, 测值 354.06；理论值 354.21。
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3H, C9-H), 1.59 (d, J = 5.2 Hz, 3H, C8-H); CNMR (Z)-柠檬醛基对-甲基苄基 1,2,3-三唑〔(Z)-Ⅴd〕：
(151 MHz, CDCl 3 ), δ: 165.84, 161.62, 143.54, 136.93,
132.27, 131.06, 129.48, 129.19, 126.55, 123.56, 无色液体，产率 82.2%，HPLC 纯度：97.47%。IR
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123.23, 115.56, 56.84, 52.36, 33.45, 26.74, 25.67, (KBr)，ν/cm : 3140 (==C—H), 2969, 2924 (C—H),