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第 7 期 王春琴，等: 2-(4-芳氧苯氧基)丙酸衍生物的合成及除草活性 ·1205·

75.00, 106.09, 116.47, 118.63, 120.46, 120.67, 121.17, 139.82, 140.13, 146.89, 147.86, 155.08, 157.23,
125.93, 126.68, 127.06, 128.39, 128.98, 129.32, 170.80。Anal. Calcd. for C 27 H 19 ClN 2 O 4 ，%: C 68.87, H
132.73, 148.58, 150.47, 153.63, 154.80, 169.93。 Anal. 4.07, N 5.95, found：C 69.01, H 4.02, N 5.91。
Calcd. for C 25 H 21 FN 2 O 3 ，%: C 72.10, H 5.08, N 6.73, N-苯乙基-(R)-2-[4-(6-氯喹喔啉-2-氧基)苯氧基]
found：C 72.21, H 5.01, N 6.59。 丙酰胺（Ⅳs）：0.88 g，产率 59%，淡黄色固体，
吡啶-3-基-(R)-2-[4-(6-氯喹喔啉-2-氧基)苯氧基] m.p. 136~138 ℃，HNMR (CDCl 3 , 400 MHz)，δ: 1.57
1
丙酸酯（Ⅳp）：0.72 g，产率 51%，淡黄色固体， (d, J=8.4 Hz, 3H, CH 3 ), 2.71~2.88 (m, 2H, CH 2 ),
1
m.p. 81~82 ℃，HNMR (CDCl 3 , 400 MHz)，δ: 1.85 (d, 3.42~3.50 (m, 1H, CH 2 ), 3.65~3.74 (m, 1H, CH 2 ),
J=6.8 Hz, 3H, CH 3 ), 5.05 (d, J=6.8Hz, 1H, CH), 7.07 4.65 (q, J =8.4 Hz, 1H, CH), 6.46 (br s, 1H, NH), 6.91
(d, J=9.2 Hz, 2H, PhH), 7.23 (d, J=9.2 Hz, 2H, PhH), (d, J=8.8 Hz, 2H, PhH), 7.07 (d, J=6.8 Hz, 2H, PhH),
7.35 (dd, J=8.4 Hz, 4.8 Hz, 1H, Py-H), 7.47~7.50 (m, 7.18~7.29 (m, 5H, Ph-H), 7.58 (dd, J=9.2 Hz, 2.4Hz,
1H, Py-H), 7.62 (dd, J=8.8Hz, 2.4 Hz, 1H, 1H, quinoxaline-H), 7.62 (d, J=9.2 Hz, 1H,
quinoxaline-H), 7.70 (d, J=8.8 Hz, 1H, quinoxaline- quinoxaline-H), 8.05 (d, J=2.4 Hz, 1H, quinoxaline-
13
H), 8.05 (d, J=2.4 Hz, 1H, quinoxaline-H), 8.41 (d, H), 8.69 (s, 1H, quinoxaline-H); CNMR (CDCl 3 , 100
J=2.8 Hz, 1H, Py-H), 8.52 (dd, J=4.8 Hz, 1.2 Hz, 1H, MHz)，δ: 18.96, 35.73, 40.07, 75.64, 116.24, 122.70,
13
Py-H), 8.69 (s, 1H, quinoxaline-H); CNMR (CDCl 3 , 126.54, 127.99, 128.69, 128.73, 128.79, 131.18, 132.93,
100 MHz)，δ: 18.59, 73.14, 116.21, 122.68, 123.99, 138.49, 138.51, 139.84, 140.11, 146.88, 154.47, 157.20,
127.93, 128.82, 129.01, 131.18, 132.91, 138.48, 171.89。Anal. Calcd. for C 25H 22ClN 3O 3，%: C 67.04, H
139.78, 140.10, 142.96, 146.93, 146.99, 147.30,
154.82, 157.15, 170.23。Anal. Calcd. for C 22H 16ClN 3O 4， 4.95, N 9.38, found：C 67.12, H 5.01, N 9.44。
(R)-四氢异喹啉-2-基-2-[4-(6-氯-喹喔啉-2-氧基)
%: C 62.64, H 3.82, N 9.96, found：C 62.59, H 4.00, N
苯氧基]丙酮（Ⅳt）：0.99 g，产率 65%，淡黄色固
10.01。
1
(R)-2-[4-(6-氯喹喔啉-2-氧基)苯氧基]丙酸苯乙 体，m.p. 48~50 ℃， HNMR (CDCl 3 , 400 MHz)，δ:
1.69 (d, J=6.8 Hz, 3H, CH 3 ), 2.74~2.95 (m, 2H, CH 2 ),
酯（Ⅳq）：1.12 g，产率 75%，白色固体，m.p. 78~ 3.95~4.04 (m, 2H, CH 2 ), 4.70~4.98 (m, 2H, CH 2 ),
1
79 ℃， HNMR (CDCl 3 , 400 MHz)，δ: 1.59 (d, J=6.8 5.06 (q, J=6.8 Hz, 1H, CH), 6.95~7.00 (m, 2H, PhH),
Hz, 3H, CH 3 ), 2.96 (t, J=7.2 Hz, 2H, CH 2 ), 4.38~4.44 7.10~ 7.21 (m, 6H, Ph-H), 7.56~7.69 (m, 2H,
(m, 2H, CH 2 ), 4.72 (q, J=6.8 Hz, 1H, CH), 6.89 (d, quinoxaline-H), 8.04 (d, J=2.4 Hz, 1H, quinoxaline-
J=7.2 Hz, 2H, PhH), 7.12~7.31 (m, 7H, PhH), 7.59 H), 8.65 (s, 1H, quinoxaline-H); 13 CNMR (CDCl 3 ,
(dd, J=7.2 Hz, 2.4 Hz, 1H, quinoxaline-H), 7.64 (d, J 100 MHz)，δ: 17.94, 29.57, 45.01, 46.87, 74.96, 115.77,
=7.2 Hz, 1H, quinoxaline-H), 8.04 (d, J=2.4 Hz, 1H,
13
quinoxaline-H), 8.67 (s, 1H, quinoxaline-H); CNMR 115.89, 122.43, 122.60, 125.92, 126.54, 126.68,
(CDCl 3 , 100 MHz)，δ: 18.60, 34.97, 65.58, 73.00, 127.93, 128.38, 128.79, 131.10, 132.83, 138.51,
139.76, 140.09, 146.55, 154.83, 157.19, 170.06 。
115.94, 122.42, 126.66, 127.92, 128.53, 128.77, +
128.87, 131.11, 132.81, 137.29, 138.52, 139.74, HRMS (ESI, posotive mode): 460.1412 (M+H )。
140.11, 146.50, 155.06, 157.22, 172.00。Anal. Calcd. 吡啶-3-基-(R)-2-[4-(6-氯苯并唑-2-氧基)苯氧
for C 25 H 21 ClN 2 O 4 ，%: C 66.89, H 4.72, N 6.24, found： 基]丙酸酯（Ⅳu）：0.93 g，产率 68%，棕黄色固体，
1
C 67.02, H 4.66, N 6.19。 熔点 105.2~107.4 ℃； HNMR (CDCl 3 , 400 MHz)，δ:
(R)-2-[4-(6-氯喹喔啉-2-氧基)苯氧基]丙酸萘酯 1.82 (d, J=6.8 Hz, 3H, CH 3 ), 5.02(q, J=6.8Hz, 1H,
（Ⅳr）：1.24 g，产率 79%，白色固体，m.p. 120~ CH), 7.05 (d, J=9.2Hz, 2H, PhH), 7.24(dd, J 1 =8.4Hz,
1
121 ℃。HNMR (CDCl 3 , 400 MHz)，δ: 1.87 (d, J=6.8 J 2 = 2.0 Hz, 1H,benzoxazole-H), 7.34(dd, J 1 =8.4 Hz,
J 2 =4.4 Hz, 1H, Py-H), 7.38(d, J=9.2 Hz, 2H, PhH),
Hz, 3H, CH 3 ), 5.06 (q, J=6.8 Hz, 1H, CH), 7.11 (d, 7.41 (d, J=8.4 Hz, 1H,benzoxazole-H), 7.45 (d, J=
J=7.2 Hz, 2H, PhH), 7.18 (dd, J=8.8 Hz, 2.4 Hz, 1H, 2.0 Hz, 1H, benzoxazole-H), 7.46~7.49 (m, 1H, Py-H),
naphthalin-H), 7.24 (d, J=7.2 Hz, 2H, PhH), 8.41 (d, J=2.8 Hz, 1H, Py-H), 8.50(dd, J 1 =4.4 Hz, J 2 =
7.45~7.52 (m, 2H, naphthalin-H), 7.55 (d, J =2.4 Hz, 13
1H, naphthalin-H),7.60 (dd, J=8.8 Hz, 2.0 Hz, 1H, 1.6 Hz, 1H, Py-H); CNMR (CDCl 3 , 100 MHz)，δ:
quinoxaline-H), 7.67 (d, J=8.8 Hz, 1H, 18.54, 73.19, 110.69, 116.48, 119.21, 121.45, 123.99,
quinoxaline-H), 7.79 (dd, J=6.4 Hz, 2.8 Hz, 1H, 124.37, 125.09, 128.95, 140.28, 142.98, 146.79,
naphthalin-H), 7.84 (dd, J=7.2 Hz, 3.2 Hz, 1H, 146.95, 147.39, 151.73, 153.17, 153.85, 169.72。Anal.
naphthalin-H), 8.05 (d, J=2.0 Hz, 2H, quinoxaline-H), Calcd. for C 21 H 15 ClN 2 O 5 ，%: C 61.40, H 3.68, N 6.82,
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8.69 (s, 1H, quinoxaline-H); CNMR (CDCl 3 , 100 found：C 61.34, H 3.77, N 6.95。
MHz)，δ: 18.66, 73.39, 116.31, 118.31, 120.52, 122.61,
125.93, 126.73, 127.66, 127.78, 127.96, 128.83, (R)-2-[4-(6-氯苯并唑-2-氧基)苯氧基]丙酸苯
129.58, 131.14, 131.59, 132.89, 133.64, 138.55, 乙酯（Ⅳv）：0.86 g，产率 59%，棕黄色固体，熔点