Page 225 - 《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 ·645·

124.83, 123.55, 121.71, 115.77, 115.54, 56.80, 47.71, 1716 (C==O), 1644, 1446 (Ar, C==C), 1138 (C—O);
33.50, 26.73, 25.65, 25.40, 17.60 。 ESI-MS, m/Z: 1 HNMR (600 MHz, CDCl 3 ), δ: 7.62 (s, 1H, C13-H),
+
[M+H] 实测值 358.03；理论值 358.19。 7.43 (dd, J = 7.9、1.2 Hz, 1H, C17-H), 7.31 (td, J =
(E)-柠檬醛基邻-氟苄基 1,2,3-三唑〔(E)- gⅤ 〕： 7.7、1.7 Hz, 1H, C18-H), 7.26 (td, J = 7.5、1.7 Hz, 1H,
无色液体，产率 87.5%，HPLC 纯度：94.56%。IR C19-H), 7.19 (dd, J = 7.6、1.6 Hz, 1H, C20-H), 5.66 (d,
–1
(KBr)，ν/cm : 3143 (==C—H), 2966, 2922 (C—H), J = 4.1 Hz, 3H, C2-H), 5.22 (s, 2H, C11-H), 5.12
1715 (C==O), 1645, 1497, 1453 (Ar, C==C), 1136 (C (dddd, J = 7.2、5.9、2.7、1.4 Hz, 1H, C6-H), 2.64~2.61
1
—O); HNMR (600 MHz, CDCl 3 ), δ: 7.64 (s, 1H, (m, 2H, C4-H), 2.13 (dd, J = 15.3、7.6 Hz, 2H, C5-H),
C13-H), 7.38 (dd, J = 14.4、6.6 Hz, 1H, C19-H), 1.88 (d, J = 1.3 Hz, 3H, C10-H), 1.67 (s, 3H, C9-H),
13
7.32~7.28 (m, 1H, C18-H), 7.18~7.12 (m, 2H, C17-H, 1.60 (s, 3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ:
C20-H), 5.69 (s, 1H, C2-H), 5.60 (s, 2H, C11-H), 5.24 165.84, 161.72, 143.78, 133.50, 132.13, 130.38,
(s, 2H, C14-H), 5.07 (s, 1H, C6-H), 2.17~2.15 (m, 7H, 130.24, 129.91, 127.61, 123.78, 123.52, 123.55,
C4-H, C5-H, C10-H), 1.69 (s, 3H, C9-H), 1.60 (s, 3H, 115.54, 56.82, 51.40, 33.51, 26.71, 25.59, 25.42,
+
13
C8-H); CNMR (151 MHz, CDCl 3 ), δ: 166.41, 161.24, 17.57。ESI-MS, m/Z: [M+H] 实测值 374.02；理论值
143.78, 132.59, 130.93, 130.65, 124.84, 123.62, 374.16。
122.90, 121.83, 121.74, 115.93, 115.79, 114.94, 56.82, (E)-柠檬醛基邻-氯苄基 1,2,3-三唑〔(E)- iⅤ 〕：
47.65, 40.99, 25.99, 25.66, 18.97, 17.69。ESI-MS, m/Z: 无色液体，产率 84.6%，HPLC 纯度：97.49%。IR
+
[M+H] 实测值 358.04；理论值 358.19。
–1
(KBr)，ν/cm : 3146 (==C—H), 2966, 2922 (C—H),
(Z)-柠檬醛基间-氟苄基 1,2,3-三唑〔(Z)- hⅤ 〕： 1715 (C==O), 1645, 1574, 1447 (Ar, C==C), 1135 (C
无色液体，产率 85.6%，HPLC 纯度：96.75%。IR —O); HNMR (600 MHz, CDCl 3 ), δ: 7.64 (s, 1H,
1
–1
(KBr)，ν/cm : 3142 (==C—H), 2963, 2932 (C—H), C13-H), 7.44 (dd, J = 8.0、1.1 Hz, 1H, C17-H), 7.32
1718 (C==O), 1644, 1593, 1453 (Ar, C==C), 1157 (C (td, J = 7.7、1.7 Hz, 1H, C18-H), 7.27 (td, J = 7.5、1.2
1
—O); HNMR (600 MHz, CDCl 3 ), δ: 7.57 (s, 1H, Hz, 1H, C19-H), 7.20 (dd, J = 7.6、1.5 Hz, 1H, C20-H),
C13-H), 7.37~7.34 (m, 1H, C19-H), 7.06 (d, J = 6.9 5.68 (s, 1H, C2-H), 5.66 (s, 2H, C11-H), 5.23 (s, 2H,
Hz, 2H, C18-H, C20-H), 6.97 (d, J = 9.2 Hz, 1H, C14-H), 5.05 (d, J = 1.3 Hz, 1H, C6-H), 2.15 (dd, J =
C16-H), 5.67 (s, 1H, C2-H), 5.52 (s, 2H, C11-H), 5.23
(s, 2H, C14-H), 5.13 (t, J = 7.1 Hz, 1H, C6-H), 7.1、1.8 Hz, 7H, C4-H, C5-H, C10-H), 1.67 (s, 3H,
13
2.65~2.62 (m, 2H, C4-H), 2.15 (q, J = 7.5 Hz, 2H, C9-H), 1.59 (s, 3H, C8-H); CNMR (151 MHz,
C5-H), 1.89 (s, 3H, C10-H), 1.68 (s, 3H, C9-H), 1.61 CDCl 3 ), δ: 165.84, 161.67, 143.72, 133.50, 132.33,
13
(s, 3H, C8-H); CNMR (151 MHz, CDCl 3 ), δ: 165.85, 132.24, 130.38, 130.28, 129.94, 127.61, 123.78,
163.83, 162.18, 161.77, 144.04, 136.83, 132.25, 123.55, 115.54, 56.82, 51.40, 33.51, 26.74, 25.66,
+
130.82, 123.57, 123.53, 115.76, 115.51, 114.97, 56.84, 25.42, 17.62。ESI-MS, m/Z: [M+H] 实测值 374.02；
53.44, 33.43, 26.73, 25.66, 25.41, 17.60。ESI-MS, m/Z: 理论值 374.16。
+
[M+H] 实测值 358.04；理论值 358.19。 (Z)-柠檬醛基间-氯苄基 1,2,3-三唑〔(Z)- jⅤ 〕：
(E)-柠檬醛基间-氟苄基 1,2,3-三唑〔(E)- hⅤ 〕： 无色液体，产率 85.7%，HPLC 纯度：98.12%。IR
–1
无色液体，产率 85.6%，HPLC 纯度：98.21%。IR (KBr)，ν/cm : 3140 (==C—H), 2966, 2913 (C—H),
–1
(KBr)，ν/cm : 3143 (==C—H), 2920, 2857 (C—H), 1717 (C==O), 1646, 1576, 1436 (Ar, C==C), 1152 (C
1
1718 (C==O), 1645, 1602, 1429 (Ar, C==C), 1137 (C —O); HNMR (600 MHz, CDCl 3 ), δ: 7.56 (s, 1H,
1
—O); HNMR (600 MHz, CDCl 3 ), δ: 7.58 (s, 1H, C13-H), 7.33~7.27 (m, 2H, C19-H, C20-H), 7.26 (s,
C13-H), 7.35 (td, J = 8.0、5.9 Hz, 1H, C19-H), 1H, C16-H), 7.14 (dt, J = 7.3、1.4 Hz, 1H, C18-H),
7.06~7.03 (m, 2H, C16-H, C18-H), 6.98~6.95 (m, 1H, 5.66 (s, 1H , C2-H), 5.49 (s, 2H , C11-H), 5.22 (s, 2H,
C20-H), 5.67 (s, 1H, C2-H), 5.52 (s, 1H, C11-H), 5.23 C14-H), 5.13~5.10 (m, 1H, C6-H), 2.64~2.61 (m, 2H,
(s, 2H, C14-H), 5.05 (d, J = 3.9, 1H, C6-H), 2.14 (dd, C4-H), 2.13 (dd, J = 15.3、7.6 Hz, 2H, C5-H), 1.88 (d,
J = 5.7、2.0 Hz, 7H, C4-H, C5-H, C10-H), 1.67 (s, 3H, J = 1.3 Hz, 3H, C10-H), 1.66 (s, 3H, C9-H), 1.60 (s,
13
C9-H), 1.59 (s, 3H, C8-H); 13 CNMR (151 MHz, 3H , C8-H); CNMR (151 MHz, CDCl 3 ), δ: 165.85,
CDCl 3 ), δ: 166.41, 163.81, 162.17, 161.34, 143.98, 161.78, 144.06, 136.42, 135.02, 132.24, 130.43,
136.90, 132.59, 130.81, 123.58, 122.84, 115.88, 129.02, 128.15, 126.13, 123.53, 115.50, 56.79, 53.45,
115.11, 114.90, 56.79, 53.49, 40.97, 25.98, 25.64, 33.51, 26.73, 25.66, 25.41, 17.61 。 ESI-MS, m/Z:
+
+
18.94, 17.66。ESI-MS, m/Z: [M+H] 实测值 358.05； [M+H] 实测值 374.02；理论值 374.16。
理论值 358.19。 (E)-柠檬醛基间-氯苄基 1,2,3-三唑〔(E)-Ⅴj〕：
(Z)-柠檬醛基邻-氯苄基 1,2,3-三唑〔(Z)- iⅤ 〕： 无色液体，产率 85.4%，HPLC 纯度：97.56%。IR
无色液体，产率 85.5%，HPLC 纯度：98.34%。IR (KBr)，ν/cm : 3143 (==C—H), 2966, 2913 (C—H),
–1
–1
(KBr)，ν/cm : 3146 (==C—H), 2964, 2924 (C—H), 1715 (C==O), 1651, 1580, 1436 (Ar, C==C), 1138