新型肟酯杀菌剂的合成及其抑菌性能研究
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摘要
本研究以苯、草酸单乙酯酰氯、α-蒎烯为主要原料,通过硼氢化氧化反应、傅氏酰基化反应、肟化反应、酯交换反应等主要过程合成了一种新型肟酯类化合物—2-(N-甲氧基)亚氨基-2-苯基乙酸异松蒎酯。将该化合物采用纸片法对霉菌进行抑菌性能测试,测试结果表明,其对霉菌的抑制性能与参照物嘧菌酯相近,具有良好的抑制效果。
(1)合成异松蒎醇的条件为:V(四氢呋喃)=50mL,0.09mol硼氢化钠, n(硼氢化钠)∶n(α-蒎烯)∶n(三氟化硼乙醚溶液)∶n(氢氧化钠)∶n(30%过氧化氢)=9∶20∶12∶36∶21,硼氢化反应温度为40℃,硼氢化反应时间为6h,氧化反应温度为50℃,氧化反应时间为1 h的条件下,异松蒎醇的产率可达91.15%。
(2)合成苯乙酮酸乙酯的条件为:以无水三氯化铝为催化剂,反应温度为20℃,n(草酸单乙酯酰氯)=0.36mol,n(苯)∶n(三氯化铝)∶n(草酸单乙酯酰氯)=6∶1.3∶1,反应时间为3h的工艺条件下,苯乙酮酸乙酯的产率可达96.17%。
(3)合成2-(N-甲氧基)亚氨基-2-苯基乙酸乙酯的条件为:n(苯乙酮酸乙酯)= 0.02mol,n(甲氧基胺盐酸盐)=0.04mol,n(甲氧基胺盐酸盐)∶n(碳酸钠)∶n(醋酸钠)= 1∶1∶0.3,V(无水乙醇)= 30 mL于无水乙醇的回流温度,反应时间为12h的工艺条件下,2-(N-甲氧基)亚氨基-2-苯基乙酸乙酯的产率为92.25%。
(4)合成2-(N-甲氧基)亚氨基-2-苯基乙酸异松蒎酯的条件为:以乙醇钠为催化剂,在反应温度为120～130℃,n(异松蒎醇)= n(乙醇钠) =0.03mol,n(2-(N-甲氧基)亚氨基-2-苯基乙酸乙酯)=0.02 mol条件下,TLC检测反应至原料点消失,粗产物经柱色谱分离[洗脱剂:V(石油醚)∶V(乙酸乙酯)=10∶1],得到产物为黄色液体,产率为47.62%。
各合成产物的化学结构经红外光谱(IR)、氢谱(1HNMR)、碳谱(13CNMR)等确证,结果与设计的目标产物分子结构一致。
In this paper, A new Oxime esters compound which was named Isopinocampheyl 2-(N-methoxy)imino-2-phenylacetate was prepared with benzene and Ethyl chloride glyoxylate,α-pinene as raw materials by Hydroboration-Oxidation reaction, Friedel-Crafts Acylation reaction, Oximation reaction and Ester-exchange reaction. The results of the bacteriostasis activities of this new type compound for the fungal were obtained by using the disk diffusion, and the results indicated that the Isopinocampheyl 2-(N-methoxy)imino-2-phenylacetate have good bacteriostasis activities and the performance similar to the counterpoint—azoxystrobin.
(1)The reaction conditions of Isopinocampheol were obtained as follows:
V(tetrahydrofuran)=50mL, n(sodium borohydride)=0.09mol, the molar ratio of sodium borohydride toα-pinene to boron trifluride ether solution to sodium hydroxide to 30% hydrogen peroxide 9:20:12:36:21, Hydroboration reaction was carried out as follows: reaction temperature 40℃, reaction time 6h, followed by the Oxidation reaction, Oxidation reaction was carried out as follows: reaction temperauter 50℃, reaction time 1h. The yield was 91.15%.
(2)The reaction conditions of Ethyl phenyl glyoxylate were obtained as follows: n(ethyl chloride glyoxylate) =0.36mol, the molar ratio of benzene to aluminum trichloride to ethyl chloride glyoxylate 6:1.3:1, reaction temperature 20℃, reaction time 3h. The yield was 96.17%.
(3)The reaction conditions of ethyl 2-(N-methoxy)imino-2-phenylacetate were obtained as follows:
n(Ethyl phenyl glyoxylate)=0.02mol, n(Methoxy amine hydrochloride)=0.04mol, the molar ratio of methoxyamine Methoxy amine hydrochloride to sodium carbonate to sodium acetate 1:1:0.3, V(absolute ethyl alcohol)=30mL. The reaction temperature was the reflux temperature of abosolute ethyl acohol, The reaction time was 12h. The yield was 92.25%.
(4)The reaction conditions of Isopinocampheyl 2-(N-methoxy)imino-2-phenylac- tate were obtained as follows:
The reaction temperature was 120~130℃,n(Isopinocampheol)=n(Sodium ethylate)=0.03mol, n(ethyl 2-(N-methoxy)imino-2-phenylacetate)=0.02mol, The reaction that used Sodium ethylate as catalyst was monitored by TLC, which would be ended if the material point disappeared. Yellow liquid product was abtained by column chromatography separation [V(petroleum ether):V (ethyl acetate) = 10:1 as the developing solvent]. The yield of Isopinocampheyl 2-(N-methoxy)imino-2-phenyl acetate was 47.62%.
The synthetic structure that confirmed by means of IR(Infrared Spectrometry), 1HNMR(1H Nuclear Magnetic Resonance), 13CNMR(13C Nuclear Magnetic Resonance)was consistent with the molecular structure of designed target product.
(1)合成异松蒎醇的条件为:V(四氢呋喃)=50mL,0.09mol硼氢化钠, n(硼氢化钠)∶n(α-蒎烯)∶n(三氟化硼乙醚溶液)∶n(氢氧化钠)∶n(30%过氧化氢)=9∶20∶12∶36∶21,硼氢化反应温度为40℃,硼氢化反应时间为6h,氧化反应温度为50℃,氧化反应时间为1 h的条件下,异松蒎醇的产率可达91.15%。
(2)合成苯乙酮酸乙酯的条件为:以无水三氯化铝为催化剂,反应温度为20℃,n(草酸单乙酯酰氯)=0.36mol,n(苯)∶n(三氯化铝)∶n(草酸单乙酯酰氯)=6∶1.3∶1,反应时间为3h的工艺条件下,苯乙酮酸乙酯的产率可达96.17%。
(3)合成2-(N-甲氧基)亚氨基-2-苯基乙酸乙酯的条件为:n(苯乙酮酸乙酯)= 0.02mol,n(甲氧基胺盐酸盐)=0.04mol,n(甲氧基胺盐酸盐)∶n(碳酸钠)∶n(醋酸钠)= 1∶1∶0.3,V(无水乙醇)= 30 mL于无水乙醇的回流温度,反应时间为12h的工艺条件下,2-(N-甲氧基)亚氨基-2-苯基乙酸乙酯的产率为92.25%。
(4)合成2-(N-甲氧基)亚氨基-2-苯基乙酸异松蒎酯的条件为:以乙醇钠为催化剂,在反应温度为120～130℃,n(异松蒎醇)= n(乙醇钠) =0.03mol,n(2-(N-甲氧基)亚氨基-2-苯基乙酸乙酯)=0.02 mol条件下,TLC检测反应至原料点消失,粗产物经柱色谱分离[洗脱剂:V(石油醚)∶V(乙酸乙酯)=10∶1],得到产物为黄色液体,产率为47.62%。
各合成产物的化学结构经红外光谱(IR)、氢谱(1HNMR)、碳谱(13CNMR)等确证,结果与设计的目标产物分子结构一致。
In this paper, A new Oxime esters compound which was named Isopinocampheyl 2-(N-methoxy)imino-2-phenylacetate was prepared with benzene and Ethyl chloride glyoxylate,α-pinene as raw materials by Hydroboration-Oxidation reaction, Friedel-Crafts Acylation reaction, Oximation reaction and Ester-exchange reaction. The results of the bacteriostasis activities of this new type compound for the fungal were obtained by using the disk diffusion, and the results indicated that the Isopinocampheyl 2-(N-methoxy)imino-2-phenylacetate have good bacteriostasis activities and the performance similar to the counterpoint—azoxystrobin.
(1)The reaction conditions of Isopinocampheol were obtained as follows:
V(tetrahydrofuran)=50mL, n(sodium borohydride)=0.09mol, the molar ratio of sodium borohydride toα-pinene to boron trifluride ether solution to sodium hydroxide to 30% hydrogen peroxide 9:20:12:36:21, Hydroboration reaction was carried out as follows: reaction temperature 40℃, reaction time 6h, followed by the Oxidation reaction, Oxidation reaction was carried out as follows: reaction temperauter 50℃, reaction time 1h. The yield was 91.15%.
(2)The reaction conditions of Ethyl phenyl glyoxylate were obtained as follows: n(ethyl chloride glyoxylate) =0.36mol, the molar ratio of benzene to aluminum trichloride to ethyl chloride glyoxylate 6:1.3:1, reaction temperature 20℃, reaction time 3h. The yield was 96.17%.
(3)The reaction conditions of ethyl 2-(N-methoxy)imino-2-phenylacetate were obtained as follows:
n(Ethyl phenyl glyoxylate)=0.02mol, n(Methoxy amine hydrochloride)=0.04mol, the molar ratio of methoxyamine Methoxy amine hydrochloride to sodium carbonate to sodium acetate 1:1:0.3, V(absolute ethyl alcohol)=30mL. The reaction temperature was the reflux temperature of abosolute ethyl acohol, The reaction time was 12h. The yield was 92.25%.
(4)The reaction conditions of Isopinocampheyl 2-(N-methoxy)imino-2-phenylac- tate were obtained as follows:
The reaction temperature was 120~130℃,n(Isopinocampheol)=n(Sodium ethylate)=0.03mol, n(ethyl 2-(N-methoxy)imino-2-phenylacetate)=0.02mol, The reaction that used Sodium ethylate as catalyst was monitored by TLC, which would be ended if the material point disappeared. Yellow liquid product was abtained by column chromatography separation [V(petroleum ether):V (ethyl acetate) = 10:1 as the developing solvent]. The yield of Isopinocampheyl 2-(N-methoxy)imino-2-phenyl acetate was 47.62%.
The synthetic structure that confirmed by means of IR(Infrared Spectrometry), 1HNMR(1H Nuclear Magnetic Resonance), 13CNMR(13C Nuclear Magnetic Resonance)was consistent with the molecular structure of designed target product.
引文
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