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第 8 期 林桂汕，等: 紫苏醛基肟酯化合物的合成及性能 ·1437·

C7-H), 7.77 (d, J = 8.4 Hz, 1H, C17-H), 7.49 (d, 3078 (Ar — H), 2979, 2933, 2886 (C—H), 1741
J = 1.9 Hz, 1H, C14-H), 7.32 (dd, J = 8.4、2.0 Hz, 1H, (C==O), 1639, 1585, 1486, 1455, 1429 (Ar—C==C,
C16-H), 6.35~6.28 (m, 1H, C2-H), 4.75 (d, J = 23.2 Hz, C==C, C==N); HNMR (600 MHz, CDCl 3 ), δ: 8.06 (s,
1
2H, C9-H), 2.65 (dd, J = 11.4、8.8 Hz, 1H, C6-Hb), 1H, C7-H), 7.88 (d, J = 7.8 Hz, 1H, C17-H), 7.42 (td,
2.43~2.33 (m, 2H, C6-Ha, C3-Hb), 2.28~2.21 (m, 1H, J = 7.6、1.2 Hz, 1H, C15-H), 7.26 (dd, J = 13.6、7.4 Hz,
C4-H), 2.21~2.13 (m, 1H, C3-Ha), 1.97~1.91 (m, 1H, 2H, C14-H, C16-H), 6.29 (s, 1H, C2-H), 4.76 (d, J =
C5-Hb), 1.76 (s, 3H, C10-H), 1.56~1.48 (m, 1H, 20.2 Hz, 2H, C9-H), 2.72~2.66 (m, 1H, C6-Hb), 2.62
13
C5-Ha); CNMR (151 MHz, CDCl 3), δ: 162.82 (C-11), (s, 3H, C18-H), 2.40 (ddd, J = 13.1、7.5、4.6 Hz, 2H,
159.84 (C-7), 148.62 (C-1), 141.59 (C-2), 138.51
(C-8), 134.73 (C-15), 132.29 (C-13), 132.08 (C-17), C6-Ha, C3-Hb), 2.29~2.22 (m, 1H, C4-H), 2.21~2.13
130.93 (C-14), 127.72 (C-12), 127.12 (C-16), 109.39 (m, 1H, C3-Ha), 1.98~1.92 (m, 1H, C5-Hb), 1.77 (s,
(C-9), 40.52 (C-4), 31.76 (C-3), 26.48 (C-5), 23.62 3H, C10-H), 1.53 (ddd, J = 24.3、11.4、5.4 Hz, 1H,
13
+
(C-6), 20.74 (C-10)。ESI-MS, m/Z: [M+H] , 实测值, C5-Ha); CNMR (151 MHz, CDCl 3 ), δ: 165.22 (C-11),
159.13 (C-7), 148.73 (C-1), 140.73 (C-2), 140.34
337.75, 理论值, 337.06。
(C-8), 132.36 (C-13), 132.16 (C-15), 131.72 (C-12),
紫苏醛基对氯甲基苯基肟酯（Ⅲo）：白色固体, 130.17 (C-17), 128.42 (C-14), 125.71 (C-16), 109.33
0.88 g, 产率 83.7%。熔点 104~106 ℃。IR (KBr), (C-9), 40.59 (C-4), 31.72 (C-3), 26.55 (C-5), 23.71
–1
ν/cm : 3036 (Ar–H), 2973, 2922 (C—H), 1739 (C-6), 21.48 (C-10), 20.75 (C-18)。ESI-MS, m/Z:
(C==O), 1643, 1588, 1416 (Ar—C==C, C==C, C==N); [M+H] , 实测值, 283.87, 理论值, 283.16。
+
1 HNMR (600 MHz, CDCl 3 ), δ: 8.09 (s, 1H, C7-H), 紫苏醛基间甲基苯基肟酯（Ⅲr）：白色固体, 0.77
8.09~8.05 (m, 2H, C13-H, C17-H), 7.48 (d, J = 8.4 Hz, –1
2H, C14-H, C16-H), 6.31 (d, J = 2.3 Hz, 1H, C2-H), g, 产率 82.4%。熔点 70~71 ℃。IR (KBr), ν/cm :
4.79~4.72 (m, 2H, C9-H), 4.62 (s, 2H, C18-H), 3083, 3047 (Ar–H), 2932, 2890 (C—H), 1738 (C==O),
2.71~2.64 (m, 1H, C6-Hb), 2.43~2.34 (m, 2H, C6-Ha, 1639, 1612, 1583, 1428 (Ar—C==C, C==C, C==N);
C3-Hb), 2.25 (ddd, J = 11.2、6.8、2.9 Hz, 1H, C4-H), 1 HNMR (600 MHz, CDCl 3 ), δ: 8.10 (s, 1H, C7-H),
2.21~2.13 (m, 1H, C3-Ha), 1.97~1.91 (m, 1H, C5-Hb), 7.91~7.85 (m, 2H, C13-H, C17-H), 7.39 (d, J = 7.6 Hz,
1.76 (s, 3H, C10-H), 1.53 (dtd, J = 12.9、11.4、5.4 Hz, 1H, C16-H), 7.34 (t, J = 7.6 Hz, 1H, C15-H), 6.30 (dd,
13
1H, C5-Ha); CNMR (151 MHz, CDCl 3 ), δ: 163.68 J = 4.9、2.5 Hz, 1H, C2-H), 4.76 (dd, J = 11.4、10.0 Hz,
(C-11), 159.41 (C-7), 148.70 (C-1), 142.59 (C-2), 2H, C9-H), 2.72~2.65 (m, 1H, C6-Hb), 2.44~2.35 (m,
141.02 (C-8), 132.25 (C-15), 130.07 (C-12), 128.86 5H, C18-H, C6-Ha, C3-Hb), 2.29~2.22 (m, 1H, C4-H),
(C-13, C-17), 128.60 (C-14, C-16), 109.35 (C-9), 2.17 (dddd, J = 9.0、6.1、3.6、1.7 Hz, 1H, C3-Ha), 1.94
45.31 (C-18), 40.56 (C-4), 31.74 (C-3), 26.52 (C-5), (dtd, J = 12.6、4.9、2.4 Hz, 1H, C5-Hb), 1.76 (s, 3H,
+
23.70 (C-6), 20.74 (C-10)。ESI-MS, m/Z: [M+H] , 实 C10-H), 1.53 (dtd, J = 12.8、11.4、5.4 Hz, 1H, C5-Ha);
测值, 317.79, 理论值, 317.12。 13 CNMR (151 MHz, CDCl 3 ), δ: 164.37 (C-11), 159.22
紫苏醛基对溴苯基肟酯（Ⅲp）：白色固体, 0.80 g, (C-7), 148.75 (C-1), 140.73 (C-2), 138.33 (C-8),
–1
产率 70.1%。熔点 86~88 ℃。IR (KBr), ν/cm : 3084 134.02 (C-14), 132.35 (C-15), 130.17 (C-13), 128.82
(Ar–H), 2958, 2931, 2886 (C—H), 1738 (C==O), 1638, (C-12), 128.37 (C-16), 126.75 (C-17), 109.32 (C-9),
40.59 (C-4), 31.73 (C-3), 26.54 (C-5), 23.73 (C-6),
1592, 1583, 1482, 1453, 1428 (Ar–C==C, C==C, +
1
C==N); HNMR (600 MHz, CDCl 3 ), δ: 8.08 (s, 1H, 21.28 (C-10), 20.74 (C-18)。ESI-MS, m/Z: [M+H] ,
C7-H), 7.93 (t, J = 5.3 Hz, 2H, C13-H, C17-H), 7.60 (t, 实测值, 283.87, 理论值, 283.16。
J = 5.3 Hz, 2H, C14-H, C16-H), 6.31 (d, J = 2.1 Hz, 紫苏醛基对甲基苯基肟酯（Ⅲs）：白色固体,
1H, C2-H), 4.76 (d, J = 21.5 Hz, 2H, C9-H), 0.69 g, 产率 73.6%。熔点 89~90 ℃。IR (KBr), ν/cm :
–1
2.71~2.63 (m, 1H, C6-Hb), 2.44~2.34 (m, 2H, C6-Ha, 3087, 3037 (Ar–H), 2924 (C—H), 1734 (C==O), 1640,
C3-Hb), 2.29~2.22 (m, 1H, C4-H), 2.22~2.13 (m, 1H,
C3-Ha), 1.98~1.91 (m, 1H, C5-Hb), 1.76 (s, 3H, 1610, 1508, 1583, 1451 (Ar–C==C, C==C, C==N);
1
HNMR (600 MHz, CDCl 3 ), δ: 8.09 (s, 1H, C7-H),
C10-H), 1.52 (ddd, J = 24.2、11.3、5.3 Hz, 1H, C5-Ha); 7.99~7.95 (m, 2H, C13-H, C17-H), 7.26 (d, J = 7.9 Hz,
13 CNMR (151 MHz, CDCl 3 ), δ: 163.48 (C-11), 159.48 2H, C14-H, C16-H), 6.29 (dd, J = 4.9、2.6 Hz, 1H,
(C-7), 148.67 (C-1), 141.16 (C-2), 132.21 (C-8), C2-H), 4.79~4.72 (m, 2H, C9-H), 2.72~2.65 (m, 1H,
131.87 (C-13, C-17), 131.12 (C-14, C-16), 128.41 C6-Hb), 2.42 (s, 3H, C18-H), 2.41~2.35 (m, 2H,
(C-12), 127.81 (C-15), 109.36 (C-9), 40.55 (C-4), C6-Ha, C3-Hb), 2.28~2.22 (m, 1H, C4-H), 2.21~2.13
31.75 (C-3), 26.50 (C-5), 23.69 (C-6), 20.74 (C-10)。 (m, 1H, C3-Ha), 1.94 (dtd, J = 12.7、5.0、2.5 Hz, 1H,
+
ESI-MS, m/Z: [M+H] , 实测值 , 347.74, 理论值 ,
C5-Hb), 1.76 (s, 3H, C10-H), 1.52 (dtd, J = 12.9、
347.05。
13
11.4、5.4 Hz, 1H, C5-Ha); CNMR (151 MHz, CDCl 3),
紫苏醛基邻甲基苯基肟酯（Ⅲq）：白色固体, δ: 164.26 (C-11), 159.11 (C-7), 148.76 (C-1), 143.99
–1
0.84 g, 产率 89.7%。熔点 76~78 ℃。IR (KBr), ν/cm : (C-2), 140.59 (C-8), 132.37 (C-15), 129.67 (C-13,