Design, Synthesis and Insecticidal Activity of 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-one Oxime Ether †

doi:10.7503/cjcu20190582

Abstract

Abstract:

Based on the intermediate derivatization method, the active fragment of oxime ether was introduced into 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one as a basic skeleton, and 32 novel compounds were designed and synthesized with the fragment of 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one. Their chemical structures were confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Single crystal X-ray diffraction of compound 2n was carried out. The result showed that compound 2n belonged to the monoclinic system and space group of 2n was P2₁/c. The initial screening activity showed that the mortality rate of compound 1i and 1g against aphids and red spiders were 78.57% and 69.95% at the concentration of 200 mg/L, respectiviely, while the mortality rate of compound 1i were 100% and 85% against aphids at the concentration of 200 and 12.5 mg/L, respectiviely. The results showed that compound 1i had the value of further development.

Key words: 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-oneoxime ether, Synthesis, Single crystal, Insecticidal activity

CLC Number:

O622.4

TrendMD:

LI Kangming,CHEN Jia,YI Yangjie,YAN Zhongzhong,YE Jiao,LONG Chuyun,LIU Aiping,HU Aixi,LI Jianming. Design, Synthesis and Insecticidal Activity of 1-(4-Chlorophenyl)-2-cyclopropylpropan-1-one Oxime Ether ^†[J]. Chem. J. Chinese Universities, 2020, 41(5): 1026.

Figures/Tables 6

References 31

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Compd.	t/h	Appearance	m. p./℃	Yield(%)	ESI-HRMS(calcd.), m/z[M+1]
1a	4.0	Yellow liquid	—	73.3	314.1208(314.1032)
1b	1.0	Yellow liquid	—	76.8	328.1436(328.1509)
1c	1.0	Yellow liquid	—	46.0	332.1116(332.1327)
1d	0.5	Yellow liquid	—	53.1	348.0807(348.1019)
1e	0.5	Yellow liquid	—	72.8	392.0325(392.0517)
1f	8.0	Yellow liquid	—	40.6	359.1102(359.1309)
1g	4.0	Yellow liquid	—	74.9	339.1207(339.1026)
1h	10.0	Yellow liquid	—	47.3	359.1125(359.1234)
1i	10.0	Colorless liquid	—	78.5	406.1502(406.1316)
1j	10.0	Yellow liquid	—	78.6	328.1409(328.1531)
1k	8.0	Yellow liquid	—	77.6	348.0826(348.1039)
1l	16.0	Yellow liquid	—	80.3	382.1102(382.0995)
1m	4.0	Yellow liquid	—	73.1	382.0509(382.0738)
1n	4.0	Yellow liquid	—	38.6	350.1016(350.1103)
2a	5.0	Yellow liquid	—	71.9	349.0817(349.1008)
2b	5.0	Yellow liquid	—	68.0	343.1608(343.1816)
2c	5.0	Yellow liquid	—	78.7	373.1615(373.1804)
2d	5.0	Yellow liquid	—	65.0	355.0432(355.0619)
2e	5.0	Yellow liquid	—	54.4	397.1108(397.1001)
2f	5.0	Colorless liquid	—	45.5	415.1015(415.1207)
2g	5.0	Yellow liquid	—	47.6	431.1014(431.1226)
2h	5.0	Yellow solid	41—43	48.5	465.1005(465.1034)
2i	5.0	Yellow solid	52—54	46.1	411.1026(411.1204)
2j	5.0	Yellow liquid	—	50.1	465.1119(465.1205)
2k	5.0	Yellow liquid	—	46.9	411.1047(411.1234)
2l	5.0	Colorless liquid	—	64.3	381.1008(381.0914)
2m	5.0	Colorless liquid	—	62.3	399.1207(399.1025)
2n	5.0	White solid	60—62	62.2	415.1029(415.1212)
2o	5.0	White solid	54—56	54.9	449.1219(449.1222)
2p	5.0	White solid	71—73	53.2	395.1025(395.1215)
2q	5.0	Yellow liquid	—	57.4	449.1008(449.0910)
2r	5.0	Colorless liquid	—	52.7	395.1416(395.1213)

Compd.	t/h	Appearance	m. p./℃	Yield(%)	ESI-HRMS(calcd.), m/z[M+1]
1a	4.0	Yellow liquid	—	73.3	314.1208(314.1032)
1b	1.0	Yellow liquid	—	76.8	328.1436(328.1509)
1c	1.0	Yellow liquid	—	46.0	332.1116(332.1327)
1d	0.5	Yellow liquid	—	53.1	348.0807(348.1019)
1e	0.5	Yellow liquid	—	72.8	392.0325(392.0517)
1f	8.0	Yellow liquid	—	40.6	359.1102(359.1309)
1g	4.0	Yellow liquid	—	74.9	339.1207(339.1026)
1h	10.0	Yellow liquid	—	47.3	359.1125(359.1234)
1i	10.0	Colorless liquid	—	78.5	406.1502(406.1316)
1j	10.0	Yellow liquid	—	78.6	328.1409(328.1531)
1k	8.0	Yellow liquid	—	77.6	348.0826(348.1039)
1l	16.0	Yellow liquid	—	80.3	382.1102(382.0995)
1m	4.0	Yellow liquid	—	73.1	382.0509(382.0738)
1n	4.0	Yellow liquid	—	38.6	350.1016(350.1103)
2a	5.0	Yellow liquid	—	71.9	349.0817(349.1008)
2b	5.0	Yellow liquid	—	68.0	343.1608(343.1816)
2c	5.0	Yellow liquid	—	78.7	373.1615(373.1804)
2d	5.0	Yellow liquid	—	65.0	355.0432(355.0619)
2e	5.0	Yellow liquid	—	54.4	397.1108(397.1001)
2f	5.0	Colorless liquid	—	45.5	415.1015(415.1207)
2g	5.0	Yellow liquid	—	47.6	431.1014(431.1226)
2h	5.0	Yellow solid	41—43	48.5	465.1005(465.1034)
2i	5.0	Yellow solid	52—54	46.1	411.1026(411.1204)
2j	5.0	Yellow liquid	—	50.1	465.1119(465.1205)
2k	5.0	Yellow liquid	—	46.9	411.1047(411.1234)
2l	5.0	Colorless liquid	—	64.3	381.1008(381.0914)
2m	5.0	Colorless liquid	—	62.3	399.1207(399.1025)
2n	5.0	White solid	60—62	62.2	415.1029(415.1212)
2o	5.0	White solid	54—56	54.9	449.1219(449.1222)
2p	5.0	White solid	71—73	53.2	395.1025(395.1215)
2q	5.0	Yellow liquid	—	57.4	449.1008(449.0910)
2r	5.0	Colorless liquid	—	52.7	395.1416(395.1213)

Compd.	¹H NMR(400 MHz, CDCl₃), δ
1a	7.44—7.12(m, 9H, C₆H₅, C₆H₄), 5.17(s, 1H, OCH₂), 5.04(s, 1H, OCH₂), 1.85—1.80(m, 1H, CH), 1.27(d, J=7.0Hz, 1.5H, CH₃), 1.15(d, J=7.0Hz, 1.5H, CH₃), 0.92—0.07(m, 5H, Cyclo-C₃H₅)
1b	7.44—7.13(m, 8H, C₆H₄, C₆H₄), 5.18(s, 1H, OCH₂), 5.05(s, 1H, OCH₂), 2.64—2.59(m, 1H, CH), 2.36(s, 1.5H, CH₃), 2.34(s, 1.5H, CH₃), 0.90—0.10(m, 5H, Cyclo-C₃H₅)
1c	7.44—6.98(m, 8H, C₆H₄, C₆H₄), 5.22(s, 1.33H, OCH₂), 5.11(s, 0.67H, OCH₂), 1.88—1.77(m, 1H, CH), 1.26(d, J=6.8Hz, 2H, CH₃), 1.15(d, J=7.2Hz, 1H, CH₃), 0.96—0.07(m, 5H, Cyclo-C₃H₅)
1d	7.47—7.14(m, 8H, C₆H₄, C₆H₄), 5.27(s, 2H, OCH₂), 2.69—2.61(m, 1H, CH), 1.30(d, J=7.2Hz, 3H, CH₃), 0.96—0.17(m, 5H, Cyclo-C₃H₅)
1e	7.56—7.10(m, 8H, C₆H₄, C₆H₄), 5.24(s, 1.4H, OCH₂), 5.12(s, 0.6H, OCH₂), 1.85—1.78(m, 1H, CH), 1.31(d, J=7.2Hz, 2.1H, CH₃), 1.16(d, J=6.8Hz, 0.9H, CH₃), 0.97—0.12(m, 5H, Cyclo-C₃H₅)
1f	8.08—7.21(m, 8H, C₆H₄, C₆H₄), 5.57(s, 1.33H, OCH₂), 5.44(s, 0.67H, OCH₂), 1.78—1.73(m, 1H, CH), 1.34(d, J=7.2Hz, 2H, CH₃), 1.27(d, J=6.8Hz, 1H, CH₃), 1.10—0.15(m, 5H, Cyclo-C₃H₅)
1g	7.67—7.15(m, 8H, C₆H₄, C₆H₄), 5.34(s, 2H, OCH₂), 2.69—2.62(m, 1H, CH), 1.29(d, J=7.2 Hz, 3H, CH₃), 0.97—0.11(m, 5H, Cyclo-C₃H₅)
1h	8.24—7.17(m, 8H, C₆H₄, C₆H₄), 5.25(s, 2H, OCH₂), 2.68—2.61(m, 1H, CH), 1.30(d, J=7.2Hz, 3H, CH₃), 0.94—0.17(m, 5H, Cyclo-C₃H₅)
1i	7.36—6.87(m, 13H, C₆H₅, C₆H₄, C₆H₄), 5.10, 5.00(2×s, 2H, OCH₂), 1.83—1.75(m, 1H, CH), 1.22, 1.12(2×d, J₁=7.1 Hz, J₂=7.0 Hz, 3H, CH₃), 0.89—0.07(m, 5H, Cyclo-C₃H₅)
1j	7.40—7.10(m, 8H, C₆H₄, C₆H₄), 5.12(s, 1.36H, OCH₂), 5.00(s, 0.64H, OCH₂), 2.35(s, 2H, CH₃), 2.33(s, 1H, CH₃), 1.87—1.79(m, 1H, CH), 1.26(d, J=7.2Hz, 2H, CH₃), 1.15(d, J=6.8Hz, 1H, CH₃), 0.92—0.13(m, 5H, Cyclo-C₃H₅)
1k	7.37—7.11(m, 8H, C₆H₄, C₆H₄), 5.11, 4.98(2×s, 2H, OCH₂), 2.68—1.74(m, 1H, CH), 1.26, 1.14(2×d, J₁=7.0 Hz, J₂=7.0 Hz, 3H, CH₃), 0.89—0.03(m, 5H, Cyclo-C₃H₅)
1l	7.60—7.16(m, 8H, C₆H₄, C₆H₄), 5.21(s, 1.35H, OCH₂), 5.07(s, 0.65H, OCH₂), 1.83—1.78(m, 1H, CH), 1.30(d, J=7.2Hz, 2H, CH₃), 1.16(d, J=7.2Hz, 1H, CH₃), 0.96—0.07(m, 5H, Cyclo-C₃H₅)
1m	7.38—7.15(m, 7H, C₆H₄, C₆H₃), 5.10, 4.47(2×s, 2H, OCH₂), 1.87—1.79(m, 1H, CH), 1.16(d, J=7.0 Hz, 3H, CH₃), 0.72—0.08(m, 5H, Cyclo-C₃H₅)
1n	6.92—7.87(m, 7H, C₆H₄, C₆H₃), 5.20(s, 1.35H, OCH₂), 5.08(s, 0.65H, OCH₂), 1.83—1.81(m, 1H, CH), 1.29(d, J=7.2Hz, 2H, CH₃), 1.16(d, J=6.8Hz, 1H, CH₃), 0.95—0.09(m, 5H, Cyclo-C₃H₅)

Compd.	¹H NMR(400 MHz, CDCl₃), δ
1a	7.44—7.12(m, 9H, C₆H₅, C₆H₄), 5.17(s, 1H, OCH₂), 5.04(s, 1H, OCH₂), 1.85—1.80(m, 1H, CH), 1.27(d, J=7.0Hz, 1.5H, CH₃), 1.15(d, J=7.0Hz, 1.5H, CH₃), 0.92—0.07(m, 5H, Cyclo-C₃H₅)
1b	7.44—7.13(m, 8H, C₆H₄, C₆H₄), 5.18(s, 1H, OCH₂), 5.05(s, 1H, OCH₂), 2.64—2.59(m, 1H, CH), 2.36(s, 1.5H, CH₃), 2.34(s, 1.5H, CH₃), 0.90—0.10(m, 5H, Cyclo-C₃H₅)
1c	7.44—6.98(m, 8H, C₆H₄, C₆H₄), 5.22(s, 1.33H, OCH₂), 5.11(s, 0.67H, OCH₂), 1.88—1.77(m, 1H, CH), 1.26(d, J=6.8Hz, 2H, CH₃), 1.15(d, J=7.2Hz, 1H, CH₃), 0.96—0.07(m, 5H, Cyclo-C₃H₅)
1d	7.47—7.14(m, 8H, C₆H₄, C₆H₄), 5.27(s, 2H, OCH₂), 2.69—2.61(m, 1H, CH), 1.30(d, J=7.2Hz, 3H, CH₃), 0.96—0.17(m, 5H, Cyclo-C₃H₅)
1e	7.56—7.10(m, 8H, C₆H₄, C₆H₄), 5.24(s, 1.4H, OCH₂), 5.12(s, 0.6H, OCH₂), 1.85—1.78(m, 1H, CH), 1.31(d, J=7.2Hz, 2.1H, CH₃), 1.16(d, J=6.8Hz, 0.9H, CH₃), 0.97—0.12(m, 5H, Cyclo-C₃H₅)
1f	8.08—7.21(m, 8H, C₆H₄, C₆H₄), 5.57(s, 1.33H, OCH₂), 5.44(s, 0.67H, OCH₂), 1.78—1.73(m, 1H, CH), 1.34(d, J=7.2Hz, 2H, CH₃), 1.27(d, J=6.8Hz, 1H, CH₃), 1.10—0.15(m, 5H, Cyclo-C₃H₅)
1g	7.67—7.15(m, 8H, C₆H₄, C₆H₄), 5.34(s, 2H, OCH₂), 2.69—2.62(m, 1H, CH), 1.29(d, J=7.2 Hz, 3H, CH₃), 0.97—0.11(m, 5H, Cyclo-C₃H₅)
1h	8.24—7.17(m, 8H, C₆H₄, C₆H₄), 5.25(s, 2H, OCH₂), 2.68—2.61(m, 1H, CH), 1.30(d, J=7.2Hz, 3H, CH₃), 0.94—0.17(m, 5H, Cyclo-C₃H₅)
1i	7.36—6.87(m, 13H, C₆H₅, C₆H₄, C₆H₄), 5.10, 5.00(2×s, 2H, OCH₂), 1.83—1.75(m, 1H, CH), 1.22, 1.12(2×d, J₁=7.1 Hz, J₂=7.0 Hz, 3H, CH₃), 0.89—0.07(m, 5H, Cyclo-C₃H₅)
1j	7.40—7.10(m, 8H, C₆H₄, C₆H₄), 5.12(s, 1.36H, OCH₂), 5.00(s, 0.64H, OCH₂), 2.35(s, 2H, CH₃), 2.33(s, 1H, CH₃), 1.87—1.79(m, 1H, CH), 1.26(d, J=7.2Hz, 2H, CH₃), 1.15(d, J=6.8Hz, 1H, CH₃), 0.92—0.13(m, 5H, Cyclo-C₃H₅)
1k	7.37—7.11(m, 8H, C₆H₄, C₆H₄), 5.11, 4.98(2×s, 2H, OCH₂), 2.68—1.74(m, 1H, CH), 1.26, 1.14(2×d, J₁=7.0 Hz, J₂=7.0 Hz, 3H, CH₃), 0.89—0.03(m, 5H, Cyclo-C₃H₅)
1l	7.60—7.16(m, 8H, C₆H₄, C₆H₄), 5.21(s, 1.35H, OCH₂), 5.07(s, 0.65H, OCH₂), 1.83—1.78(m, 1H, CH), 1.30(d, J=7.2Hz, 2H, CH₃), 1.16(d, J=7.2Hz, 1H, CH₃), 0.96—0.07(m, 5H, Cyclo-C₃H₅)
1m	7.38—7.15(m, 7H, C₆H₄, C₆H₃), 5.10, 4.47(2×s, 2H, OCH₂), 1.87—1.79(m, 1H, CH), 1.16(d, J=7.0 Hz, 3H, CH₃), 0.72—0.08(m, 5H, Cyclo-C₃H₅)
1n	6.92—7.87(m, 7H, C₆H₄, C₆H₃), 5.20(s, 1.35H, OCH₂), 5.08(s, 0.65H, OCH₂), 1.83—1.81(m, 1H, CH), 1.29(d, J=7.2Hz, 2H, CH₃), 1.16(d, J=6.8Hz, 1H, CH₃), 0.95—0.09(m, 5H, Cyclo-C₃H₅)

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(100 MHz, CDCl₃), δ
2a	8.46—7.07(m, 3H, Pyridine-H), 7.41—7.23(m, 4H, C₆H₄), 5.14, 5.01(2s, 2H, OCH₂), 2.58—1.72(m, 1H, CH), 1.25, 1.13(2d, J₁=7.0 Hz, J₂=7.0 Hz, 3H, CH₃), 0.97—0.03(m, 5H, Cyclo-C₃H₅)
2b	8.25(s, 1H, Pyridine 6-H), 7.41—7.39(m, 2H, C₆H₄ 3,5-H), 7.31—7.29(m, 3H, Pyridine 4-H, C₆H₄ 2,6-H), 5.26(s, 2H, OCH₂), 2.64—2.58(m, 1H, CH), 2.38(s, 3H, CH₃), 2.30(s, 3H, CH₃), 1.22(d, J=7.2 Hz, 3H, CH₃), 0.85—0.10(m, 5H, Cyclo-C₃H₅)	162.78, 151.95, 147.01, 138.81, 134.62, 134.45, 132.83, 132.69, 129.30, 128.23, 76.34, 38.87, 18.18, 18.04, 17.41, 14.77, 5.24, 4.29
2c	8.23(s, 1H, Pyridine-H), 7.40(d, J=8.4 Hz, 2H, C₆H₄ 3,5-H), 7.30(d, J=8.4 Hz, 2H, C₆H₄ 2,6-H), 5.26(s, 2H, OCH₂), 3.77(s, 3H, OCH₃), 2.64—2.56(m, 1H, CH), 2.32(s, 3H, CH₃), 2.26(s, 3H, CH₃), 1.22(d, J=7.2 Hz, 3H, CH₃), 0.85—0.10(m, 5H, Cyclo-C₃H₅)	164.15, 162.90, 154.82, 149.10, 134.57, 134.48, 129.31, 128.24, 126.49, 126.16, 76.57, 59.83, 38.87, 17.41, 14.77, 13.36, 11.09, 5.24, 4.29
2d	7.48—7.35(m, 4H, C₆H₄), 7.11(s, 1H, Thiazole-H), 5.23, 5.09(2s, 2H, OCH₂), 2.59—1.78(m, 1H, CH), 1.25, 1.20(2d, J₁=7.2 Hz, J₂=7.0 Hz, 3H, CH₃), 0.93—0.08(m, 5H, Cyclo-C₃H₅)
2e	7.96—7.95(m, 2H, C₆H₅), 7.43—7.41(m, 5H, Ph, C₆H₄ 3,5-H), 7.33(d, J=8.0 Hz, 2H, C₆H₄ 2,6-H), 7.21(s, 1H, Thiazole-H), 5.36(s, 2H, OCH₂), 2.72—2.64(m, 1H, CH), 1.31(d, J=6.8 Hz, 3H, CH₃), 0.96—0.20(m, 5H, Cyclo-C₃H₅)	168.20, 163.44, 154.75, 134.64, 134.51, 133.63, 130.03, 129.29, 128.93, 128.34, 126.60, 115.92, 72.00, 39.33, 17.33, 14.83, 5.29, 4.35
2f	7.95—7.10(m, 4H, C₆H₄), 7.42(d, J=8.4 Hz, 2H, ClC₆H₄ 3,5-H), 7.32(d, J=8.4 Hz, 2H, ClC₆H₄ 2,6-H), 7.20(s, 1H, Thiazole-H), 5.33(s, 2H, OCH₂), 2.71—2.64(m, 1H, CH), 1.31(d, J=7.2 Hz, 3H, CH₃), 0.97—0.19(m, 5H, Cyclo-C₃H₅)	166.96, 165.10, 163.47, 162.61, 154.81, 134.67, 134.47, 130.00, 129.28, 128.52, 128.44, 128.34, 116.11, 115.89, 71.93, 39.32, 17.33, 14.82, 5.29, 4.35
2g	7.88(d, J=8.0 Hz, 2H, C₆H₄), 7.42—7.39(m, 4H, C₆H₄, C₆H₄), 7.32(d, J=8.4 Hz, 2H, C₆H₄), 7.22(s, 1H, Thiazole-H), 5.34(s, 2H, OCH₂), 2.71—2.63(m, 1H, CH), 1.31(d, J=7.2 Hz, 3H, CH₃), 0.95—0.19(m, 5H, Cyclo-C₃H₅)	166.79, 163.50, 155.00, 135.97, 134.68, 134.46, 132.14, 129.28, 129.16, 128.35, 127.76, 116.20, 71.90, 39.33, 17.33, 14.83, 5.31, 4.35
2h	8.07(d, 2H, J=8.4 Hz, C₆H₄ 3,5-H), 7.69(d, 2H, J=8.0 Hz, C₆H₄ 2,6-H), 7.42(d, J=8.0 Hz, 2H, ClC₆H₄ 3,5-H), 7.33(d, J=8.4 Hz, 2H, ClC₆H₄ 2,6-H), 7.29(s, 1H, Thiazole-H), 5.36(s, 2H, OCH₂), 2.71—2.64(m, 1H, CH), 1.31(d, J=7.2 Hz, 3H, CH₃), 0.96—0.19(m, 5H, Cyclo-C₃H₅)	166.22, 163.59, 155.42, 136.70, 134.72, 134.42, 131.62, 129.27, 128.36, 126.76, 125.97, 125.93, 125.26, 122.56, 117.00, 71.85, 39.35, 17.32, 14.82, 5.31, 4.35
2i	7.85(d, J=7.6 Hz, 2H, C₆H₄), 7.43(d, J=8.4 Hz, 2H, ClC₆H₄ 3,5-H), 7.33(d, J=8.4 Hz, 2H, ClC₆H₄ 2,6-H), 7.24(d, J=7.6 Hz, 2H, C₆H₄), 7.17(s, 1H, Thiazole-H), 5.35(s, 2H, OCH₂), 2.72—2.64(m, 1H, CH), 2.40(s, 3H, CH₃), 1.31(d, J=7.2 Hz, 3H, CH₃), 0.97—0.20(m, 5H, Cyclo-C₃H₅)	168.39, 163.39, 154.56, 140.26, 134.63, 134.54, 131.02, 129.61, 129.30, 128.33, 126.51, 115.45, 72.04, 39.32, 21.43, 17.34, 14.84, 5.30, 4.36
2j	7.81—7.56(m, 4H, C₆H₄), 7.42(d, J=8.0 Hz, 2H, ClC₆H₄ 3,5-H), 7.37(s, 1H, Thiazole-H), 7.33(d, J=8.0 Hz, 2H, ClC₆H₄ 2,6-H), 5.37(s, 2H, OCH₂), 2.71—2.63(m, 1H, CH), 1.30(d, J=7.2 Hz, 3H, CH₃), 0.96—0.19(m, 5H, Cyclo-C₃H₅)	164.22, 163.50, 154.13, 134.64, 134.54, 132.34, 131.61, 129.67, 129.29, 128.34, 126.67, 118.08, 71.83, 39.39, 17.28, 14.79, 5.25, 4.31
2k	7.72—7.70(m, 1H, C₆H₄), 7.44(d, J=8.4 Hz, 2H, ClC₆H₄ 3,5-H), 7.35—7.29(m, 5H, ClC₆H₄ 2,6-H, C₆H₄), 7.27(s, 1H, Thiazole-H), 5.38(s, 2H, OCH₂), 2.72—2.64(m, 1H, CH), 2.58(s, 3H, CH₃), 1.32(d, J=7.2 Hz, 3H, CH₃), 0.98— 0.20(m, 5H, Cyclo-C₃H₅)	167.72, 163.32, 153.98, 136.55, 134.65, 134.57, 133.02, 131.40, 129.96, 129.42, 129.29, 128.36, 126.05, 116.54, 72.11, 39.41, 21.35, 17.34, 14.84, 5.31, 4.39
2l	7.68(s, 1H, Oxazole-H), 8.05—7.45(m, 5H, C₆H₅), 7.42(d, J=8.4 Hz, 2H, C₆H₄ 3,5-H), 7.33(d, J=8.4 Hz, 2H, C₆H₄ 2,6-H), 5.17(s, 2H, OCH₂), 2.69—2.62(m, 1H, CH), 1.28(d, J=6.8 Hz, 3H, CH₃), 0.92—0.19(m, 5H, Cyclo-C₃H₅)	163.54, 161.79, 139.07, 136.47, 134.64, 134.49, 130.41, 129.30, 128.77, 128.33, 127.45, 126.42, 68.17, 39.18, 17.32, 14.83, 5.27, 4.31
2m	8.05—7.12(m, 4H, C₆H₄), 7.66(s, 1H, Oxazole-H), 7.41(d, J=8.4 Hz, 2H, ClC₆H₄ 3,5-H), 7.32(d, J=8.4 Hz, 2H, ClC₆H₄ 2,6-H), 5.15(s, 2H, OCH₂), 2.68—2.61(m, 1H, CH), 1.27(d, J=7.2 Hz, 3H, CH₃), 0.91—0.18(m, 5H, Cyclo-C₃H₅)	165.34, 163.59, 162.84, 160.98, 139.09, 136.50, 134.66, 134.44, 129.29, 128.58, 128.50, 128.33, 123.81, 116.08, 115.86, 68.08, 39.16, 17.31, 14.82, 5.26, 4.30
2n	7.97(d, J=8.4 Hz, 2H, C₆H₄), 7.67(s, 1H, Oxazole-H), 7.44—7.40(m, 4H, C₆H₄, C₆H₄), 7.32(d, J=8.0 Hz, 2H, C₆H₄), 5.15(s, 2H, OCH₂), 2.68—2.60(m, 1H, CH), 1.27(d, J=7.2 Hz, 3H, CH₃), 0.91—0.17(m, 5H, Cyclo-C₃H₅)	163.61, 160.86, 139.28, 136.67, 136.53, 134.68, 134.43, 129.28, 129.10, 128.33, 127.68, 125.93, 68.06, 39.17, 17.31, 14.82, 5.27, 4.31
2o	8.16—7.72(m, 4H, C₆H₄), 7.70(s, 1H, Oxazole-H), 7.41(d, J=8.0 Hz, 2H, ClC₆H₄ 3,5-H), 7.32(d, J=8.4 Hz, 2H, ClC₆H₄ 2,6-H), 5.17(s, 2H, OCH₂), 2.69—2.61(m, 1H, CH), 1.28(d, J=7.2 Hz, 3H, CH₃), 0.92—0.18(m, 5H, Cyclo-C₃H₅)	163.67, 160.36, 139.66, 137.22, 134.71, 134.41, 131.98, 130.55, 129.27, 128.34, 126.63, 125.81, 125.78, 125.19, 122.49, 68.00, 39.21, 17.28, 14.81, 5.27, 4.30
2p	7.94—7.27(m, 4H, C₆H₄), 7.65(s, 1H, Oxazole-H), 7.41(d, J=8.0 Hz, 2H, ClC₆H₄ 3,5-H), 7.33(d, J=8.0 Hz, 2H, ClC₆H₄ 2,6-H), 5.15(s, 2H, OCH₂), 2.69—2.61(m, 1H, CH), 2.40(s, 3H, CH₃), 1.27(d, J=7.2 Hz, 3H, CH₃), 0.91—0.18(m, 5H, Cyclo-C₃H₅)	163.53, 162.02, 140.71, 138.87, 136.15, 134.62, 134.50, 129.48, 129.30, 128.32, 126.39, 124.76, 68.20, 39.16, 21.52, 17.31, 14.82, 5.25, 4.29
2q	8.02—7.57(m, 4H, C₆H₄), 7.77(s, 1H, Oxazole-H), 7.41(d, J=8.4 Hz, 2H, ClC₆H₄ 3,5-H), 7.33(d, J=8.0 Hz, 2H, ClC₆H₄ 2,6-H), 5.19(s, 2H, OCH₂), 2.68—2.60(m, 1H, CH), 1.28(d, J=6.8 Hz, 3H, CH₃), 0.92—0.18(m, 5H, Cyclo-C₃H₅)	163.70, 159.75, 139.19, 137.71, 134.67, 134.46, 131.83, 131.62, 130.31, 129.29, 128.34, 126.85, 68.07, 39.28, 17.27, 14.79, 5.25, 4.27
2r	7.99—7.28(m, 3H, C₆H₄), 7.70(s, 1H, Oxazole-H), 7.42(d, J=8.4 Hz, 2H, ClC₆H₄ 3,5-H), 7.34—7.32(m, 3H, ClC₆H₄ 2,6-H, C₆H₄), 5.19(s, 2H, OCH₂), 2.69(s, 3H, CH₃), 2.67—2.61(m, 1H, CH), 1.29(d, J=7.2 Hz, 3H, CH₃), 0.94—0.19(m, 5H, Cyclo-C₃H₅)	163.45, 162.22, 138.76, 137.48, 136.02, 134.64, 134.54, 131.56, 129.99, 129.28, 128.95, 128.34, 126.56, 125.93, 68.31, 39.28, 21.87, 17.30, 14.82, 5.27, 4.33