CN111943939B - Synthesis method of chromanone compound and agricultural biological activity thereof - Google Patents
Synthesis method of chromanone compound and agricultural biological activity thereof Download PDFInfo
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Abstract
The invention provides a synthesis method of chromanone compounds and agricultural biological activity thereof, belonging to the field of organic synthesis. The technical scheme comprises the steps of respectively adding a 2- (allyloxy) benzaldehyde compound and 2-hydroxy isoindoline-1, 3-diketone into a reactor, and heating and reacting in a closed manner for 5-8 hours at 50-100 ℃ in the presence of a catalyst and a eutectic solvent; and after the reaction is finished, performing column chromatography separation to obtain the chromanone compounds. The compound synthesized by the invention can be applied to the control of apple tree canker Valsa mali and citrus anthracnose Colletotrichum gloeosporioides Penz singly or in combination.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of chromanone compounds and agricultural biological activity thereof.
Background
Chromanone compounds have various biological activities, have achieved various satisfactory effects in recent years, and are receiving increasing attention from chemical researchers all over the world. Currently, a currently available method for preparing chromanone compounds is to use 2- (allyloxy) benzaldehyde compounds and acid compounds to react under the conditions of expensive metallic silver catalysts and organic solvents at high temperature (both chem.commun.2016,52,3661 and adv.synth.catal.2017,359, 2390-2395). However, in the above preparation process, the metal silver catalyst used is expensive and used in a large amount, and the organic solvent is not only not recyclable but also not environmentally friendly. Therefore, the method provided at present is not economical and is not the optimal scheme in the experimental synthesis of the chromanone compounds.
Disclosure of Invention
The invention provides a synthesis method of chromanone compounds and agricultural biological activity thereof, the synthesis method has simple reaction system, does not need to use metal catalyst, can recycle solvent and provides a brand-new method for green synthesis of chromanone compounds.
In order to achieve the above object, the present invention provides a method for synthesizing chromanone compounds, comprising the steps of:
respectively adding a 2- (allyloxy) benzaldehyde compound and 2-hydroxyisoindoline-1, 3-diketone into a reactor, and carrying out closed heating reaction for 5-8 hours at 50-100 ℃ in the presence of a catalyst and a eutectic solvent;
and after the reaction is finished, performing column chromatography separation to obtain the chromanone compounds.
Preferably, the 2- (allyloxy) benzaldehyde compound has the following structural formula (A):
wherein，R1Selected from any one of hydrogen, chloro and tert-butyl, R2Selected from any one of hydrogen and methoxy, R3Any one selected from hydrogen, chloro and tert-butyl.
Preferably, the eutectic solvent is a mixture of choline chloride and urea.
Preferably, the molar ratio of choline chloride to urea in the eutectic solvent is 1: 1.
Preferably, the chromanone compound has the following structural formula (B):
wherein R is4Selected from any one of hydrogen, chloro and tert-butyl, R5Selected from any one of hydrogen and methoxy, R6Any one selected from hydrogen, chloro and tert-butyl.
Preferably, the catalyst is 2, 3-dichloro-5, 6-dicyan-p-benzoquinone or persulfate, wherein the persulfate is potassium persulfate or sodium persulfate.
Preferably, the millimole ratio of the 2- (allyloxy) benzaldehyde compound, the 2-hydroxyisoindoline-1, 3-diketone and the catalyst is 1:1: 2.
Preferably, the chromatographic column used in the column chromatography is a silica gel column, and the eluent used is a mixture of ethyl acetate and petroleum ether, and the volume ratio of the ethyl acetate to the petroleum ether is 1:5-2: 1.
The invention also provides application of the chromanone compound synthesized by the synthesis method according to any one of the technical schemes in prevention and treatment of apple tree canker Valsa mali and citrus anthracnose Colletotrichum gloeosporioides Penz.
Compared with the prior art, the invention has the advantages and positive effects that:
the synthesis method provided by the invention takes the 2- (allyloxy) benzaldehyde compound and the nitrobenzene compound as basic raw materials, and can complete the reaction by using cheap and easily obtained persulfate or DDQ under the condition of no need of a metal catalyst and an organic solvent. The synthesis method has the advantages that the reaction system is simple, the used solvent is a eutectic solvent, the solvent can be effectively recycled, the efficiency can still be maintained without being obviously reduced after the solvent is recycled for 8 times, the reaction can be completed under the air condition, the reaction time is short, the yield is high, and an optimal solution is provided for green synthesis of the chromanone compounds.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The embodiment of the invention provides a synthesis method of chromanone compounds, which comprises the following steps:
s1: respectively adding 2- (allyloxy) benzaldehyde compounds and 2-hydroxy isoindoline-1, 3-diketone into a reactor, and heating and reacting in a closed manner at 50-100 ℃ for 5-8 hours under the action of a catalyst and a eutectic solvent.
In the step, 2- (allyloxy) benzaldehyde compounds and 2-hydroxy isoindoline-1, 3-dione are utilized to synthesize chromanone compounds, specifically, under the heating condition, a catalyst DDQ or potassium persulfate is used for capturing hydrogen atoms of the 2-hydroxy isoindoline-1, 3-dione under the action of a eutectic solvent to generate free radicals, the free radicals are added with double bonds in the 2- (allyloxy) benzaldehyde compounds to generate carbon free radicals, the carbon free radicals and aldehyde groups are subjected to intramolecular cyclization reaction to generate oxygen free radicals, and finally the hydrogen free radicals are captured to generate target products. It should be noted here that the reaction does not need metal catalyst, and the eutectic solvent used is recyclable solvent, the method selectivity and economy are both good, and the product yield can be as high as 90%.
The residual eutectic solvent used in the above steps is added into the synthesis of new chromanone compounds, and can be recycled for 8 times without obvious reduction of yield, and the yield data is as follows (the recycling test is carried out by taking the following P1 compound as an example): :
s2: and after the reaction is finished, performing column chromatography separation to obtain the chromanone compounds.
In a preferred embodiment, the 2- (allyloxy) benzaldehyde compound has the following structural formula (a):
wherein R is1Selected from any one of hydrogen, chloro and tert-butyl, R2Selected from any one of hydrogen and methoxy, R3Any one selected from hydrogen, chloro and tert-butyl.
In a preferred embodiment, the eutectic solvent is a mixture of choline chloride and urea in a molar ratio of 1: 1. In a preferred embodiment, the catalyst is 2, 3-dichloro-5, 6-dicyan-p-benzoquinone or potassium persulfate.
In a preferred embodiment, the chromanone compound has the following structural formula (B):
wherein R is4Selected from any one of hydrogen, chloro and tert-butyl, R5Selected from any one of hydrogen and methoxy, R6Any one selected from hydrogen, chloro and tert-butyl.
Specifically, it may be selected from any one of the following compounds:
In a preferred embodiment, the millimolar ratio of the 2- (allyloxy) benzaldehyde compound, the 2-hydroxyisoindoline-1, 3-dione and the catalyst is 1:1: 2. In this example, specific ratios of the 2- (allyloxy) benzaldehyde compound, 2-hydroxyisoindoline-1, 3-dione, and catalyst are given, wherein the ratio of the 2- (allyloxy) benzaldehyde compound, 2-hydroxyisoindoline-1, 3-dione, and catalyst is set based on the reaction mechanism requirements, and the amount of solvent added is relatively excessive to ensure sufficient reaction, in order to obtain the desired core structure of the compound accurately.
In a preferred embodiment, the chromatographic column used in the column chromatography is a silica gel column, and the eluent used is a mixture of ethyl acetate and petroleum ether, and the volume ratio of the ethyl acetate to the petroleum ether is 1:5-2: 1. In this example, the product obtained by the reaction was subjected to gradient elution using a silica gel column to isolate the desired synthetic product. In this example, a mixture of ethyl acetate and petroleum ether in a volume ratio of 1:5 to 2:1 is selected for gradient elution according to the principle of similar phase solubility and considering the polarity of the synthesized product, and within this range, the skilled person can adjust the elution according to the actual situation.
The embodiment of the invention also provides application of the chromanone compound synthesized by the synthesis method in any one of the embodiments in apple tree canker Valsa mali and citrus Colletotrichum gloeosporioides Penz. Specifically, the prepared compound can be used for protecting and treating apples and citrus by single or combined administration according to needs.
In order to more clearly and specifically describe the synthesis method of the chromanone compounds and the agricultural biological activity thereof provided in the embodiments of the present invention, the following description will be given with reference to specific examples.
Example 1
1mmol of the mixture is added into a reactor respectively
1mmol
mmol potassium persulfate and 2ml eutectic solvent are sealed and heated for reaction for 5 hours at 60 ℃ under the air condition; after the reaction was completed, column chromatography was performed to obtain the following P1 compound:
the above yellow solid powder was subjected to nuclear magnetic spectrum analysis, and the data were as follows:
1H NMR(500MHz,CDCl3)δ7.88-7.84(m,3H),7.77(dd,J＝5.4,3.1Hz,2H),7.52-7.47(m,1H),7.05-6.99(m,2H),4.94(dd,J＝11.5,4.9Hz,1H),4.74-4.65(m,2H),4.41(t,J＝10.0Hz,1H),3.34(ddd,J＝14.2,9.4,4.4Hz,1H)；
13C NMR(126MHz,CDCl3)δ190.6,163.4,161.9,136.3,134.7,128.8,127.3,123.7,121.6,120.6,118.1,74.0,68.6,45.5；
HRMS:m/z C18H13O5NNa[M+Na]+calculated values are 346.06842; theoretical value 346.06859;
after identification, the spectral data correspond to the structural formula, and the synthesized 2- ((4-oxo chroman-3-yl) methoxyl) isoindoline-1, 3-diketone is proved to have the yield of 90 percent.
Example 2
1mmol of the mixture is added into a reactor respectively
1mmol
2mmol of 2, 3-dichloro-5, 6-dicyan p-benzoquinone and 2ml of eutectic solvent are sealed and heated for reaction for 5 hours at the temperature of 100 ℃ in air; after the reaction was completed, column chromatography was performed to obtain the following P2 compound:
The white solid powder was subjected to nuclear magnetic spectrum analysis, and the data were as follows:
1H NMR(500MHz,CDCl3)δ7.85(dd,J＝5.4,3.1Hz,2H),7.80-7.76(m,2H),7.73(d,J＝2.5Hz,1H),7.57(d,J＝2.5Hz,1H),5.09(dd,J＝11.6,5.1Hz,1H),4.78(t,J＝11.3Hz,1H),4.69(dd,J＝10.8,4.1Hz,1H),4.46(dd,J＝10.7,8.8Hz,1H),3.37(ddt,J＝11.0,9.0,4.7Hz,1H)；
13C NMR(126MHz,CDCl3)δ188.9,163.3,156.1,135.8,134.7,128.7,126.8,125.3,124.0,123.7,122.1,73.5,69.4,45.0；
HRMS:m/z C18H11O5NCl2Na[M+Na]+calculated value 413.99023; theoretical value 413.99065;
after identification, the spectral data correspond to the structural formula, and the synthesized product is 2- ((6, 8-dichloro-4-oxochroman-3-yl) methoxy) isoindoline-1, 3-dione with the yield of 91 percent.
Example 3
1mmol of the mixture is added into a reactor respectively
1mmol
2mmol potassium persulfate and 2ml eutectic solvent are sealed and heated for reaction for 8 hours at 50 ℃ under the air condition; after the reaction was completed, column chromatography was performed to obtain the following P3 compound:
the white solid powder was subjected to nuclear magnetic spectrum analysis, and the data were as follows:
1H NMR(500MHz,CDCl3)δ7.85(dd,J＝5.4,3.1Hz,2H),7.81-7.74(m,3H),6.57(dd,J＝8.8,2.4Hz,1H),6.45(d,J＝2.4Hz,1H),4.90(dd,J＝11.4,4.8Hz,1H),4.69(ddd,J＝10.5,10.0,6.9Hz,2H),4.39(t,J＝10.1Hz,1H),3.85(s,3H),3.26(ddd,J＝14.1,9.6,4.4Hz,1H)；
13C NMR(126MHz,CDCl3)δ189.1,166.3,163.9,163.4,134.6,129.0,128.8,123.6,114.5,110.3,100.7,74.2,68.8,55.7,45.1；HRMS:m/z C19H15O6NNa[M+Na]+calculated value 376.07858; theoretical value 376.07916;
after identification, the spectral data correspond to the structural formula, and the synthesized 2- ((7-methoxy-4-oxochroman-3-yl) methoxy) isoindoline-1, 3-dione is proved to be obtained with the yield of 93 percent.
Example 4
1mmol of the mixture is added into a reactor respectively
1mmol
2mmol potassium persulfate and 2ml eutectic solvent are sealed and heated for reaction for 8 hours at 60 ℃ under the air condition; after the reaction was completed, column chromatography was performed to obtain the following P4 compound:
the white solid powder was subjected to nuclear magnetic spectrum analysis, and the data were as follows:
1H NMR(500MHz,CDCl3)δ7.85(dd,J＝5.5,3.1Hz,2H),7.81-7.75(m,3H),7.43(dd,J＝8.9,2.7Hz,1H),6.99(d,J＝8.9Hz,1H),4.95(dd,J＝11.6,5.0Hz,1H),4.74-4.60(m,2H),4.41(dd,J＝10.6,9.2Hz,1H),3.41-3.26(m,1H)；
13C NMR(126MHz,CDCl3)δ189.6,163.4,160.3,136.2,134.7,128.7,127.1,126.5,123.7,121.4,119.8,73.7,68.7,45.2；
HRMS:m/z C18H12O5NClNa[M+Na]+calculated value 380.02911; theory of the invention A value of 380.02962;
after identification, the spectral data correspond to the structural formula, and the synthesized 2- ((6-chloro-4-oxochroman-3-yl) methoxy) isoindoline-1, 3-dione is proved to have the yield of 95%.
Example 5
1mmol of the mixture is added into a reactor respectively
1mmol
2mmol of 2, 3-dichloro-5, 6-dicyan p-benzoquinone and 2ml of eutectic solvent are sealed and heated for reaction for 7 hours at 80 ℃ in air; after the reaction was completed, column chromatography was performed to obtain the following P5 compound:
the white solid powder was subjected to nuclear magnetic spectrum analysis, and the data were as follows:
1H NMR(500MHz,CDCl3)δ7.85(dd,J＝5.4,3.1Hz,2H),7.80-7.73(m,3H),7.57(d,J＝2.5Hz,1H),4.92(dd,J＝11.3,4.7Hz,1H),4.69(ddd,J＝9.8,7.4,3.3Hz,2H),4.41(t,J＝10.1Hz,1H),3.39-3.21(m,1H),1.42(s,9H),1.30(s,9H)；
13C NMR(126MHz,CDCl3)δ191.5,163.4,159.1,143.5,138.6,134.7,131.1,128.9,123.7,121.2,120.7,74.3,68.0,45.4,35.1,34.5,31.3,29.7；
HRMS:m/z C26H29O5NNa[M+Na]+calculated value 458.19321; theoretical value 458.19379;
after identification, the spectral data correspond to the structural formula, and the synthesized product is 2- ((6, 8-di-tert-butyl-4-oxo chroman-3-yl) methoxyl) isoindoline-1, 3-diketone with the yield of 96 percent.
Performance testing
Weighing 30mg of compound, adding 3mL of acetone, and dissolving to prepare a liquid medicine mother liquor with the concentration of 10000 mg/L; taking 0.5mL of the above mother liquor, adding 2mL of acetone, and dissolving to obtain 2000mg/L medicinal liquid. Adding 2.5mL of the liquid medicine with the concentration of 2000mg/L into 100mL of the molten PDA culture medium, fully and uniformly mixing to prepare a toxic culture medium, uniformly pouring the toxic culture medium into 6 culture dishes with the length of 6cm, and cooling to form a flat plate. 2.5mL of acetone was added to 100mL of melted PDA medium as a blank (CK). The apple rot and the citrus anthracnose germ cakes are respectively inoculated to the PDA culture medium for culture, and each treatment is repeated three times. The inoculated plates were sealed and placed in an incubator (28 ℃) for culture, and the colony diameter was measured when the colonies of the white control strain grew to about 3/4 in the petri dish. The colony growth inhibition rate was calculated according to the following formula, and the test results are shown in table 1.
Inhibition/% ([ control colony diameter-treated colony diameter ]/control colony diameter × 100)
TABLE 1 controlling effect of each compound at 50mg/L
As can be seen from the data in Table 1, the compounds prepared by the above embodiments of the present invention have good control effect on apple tree canker, especially the P5 compound shows more excellent treatment effect at 50mg/L, and the treatment effect can reach more than 80; similarly, the compounds have good control effects on the citrus anthracnose pathogen, particularly the P1 compound has more excellent treatment effect at 50mg/L, and the treatment effect can reach more than 90; therefore, in order to effectively exert a controlling effect, the compounds prepared in the above examples may be selected for use alone or in combination in order to obtain a better controlling effect.
Claims (7)
1. The synthesis method of the chromanone compound is characterized by comprising the following steps:
respectively adding a 2- (allyloxy) benzaldehyde compound and 2-hydroxyisoindoline-1, 3-diketone into a reactor, and carrying out closed heating reaction for 5-8 hours at 50-100 ℃ in the presence of a catalyst and a eutectic solvent;
after the reaction is finished, performing column chromatography separation to obtain chromanone compounds;
Wherein, the 2- (allyloxy) benzaldehyde compound has the following structural formula (A):
R1selected from any one of hydrogen, chloro and tert-butyl, R2Selected from any one of hydrogen and methoxy, R3Any one selected from hydrogen, chloro and tert-butyl;
the catalyst is 2, 3-dichloro-5, 6-dicyan p-benzoquinone or persulfate, and the persulfate is potassium persulfate or sodium persulfate.
2. A synthesis process according to claim 1, characterized in that the eutectic solvent is a mixture of choline chloride and urea.
3. The synthesis method according to claim 2, characterized in that the molar ratio of choline chloride and urea in the eutectic solvent is 1: 1.
4. The method of claim 1, wherein the chromanone compound is of the formula (B):
wherein R is4Selected from any one of hydrogen, chloro and tert-butyl, R5Selected from any one of hydrogen and methoxy, R6Is selected from any one of hydrogen, chlorine and tertiary butyl.
5. The synthesis method according to claim 1, wherein the millimolar ratio of the 2- (allyloxy) benzaldehyde compound, the 2-hydroxyisoindoline-1, 3-dione and the catalyst is 1:1: 2.
6. The synthesis method according to claim 1, wherein the chromatographic column used in the column chromatography is a silica gel column, and the eluent used is a mixture of ethyl acetate and petroleum ether, and the volume ratio of the ethyl acetate to the petroleum ether is 1:5-2: 1.
7. The chromanone compound synthesized by the synthesis method according to any one of claims 1 to 6 and used for the treatment of apple tree cankerValsa maliAnd Colletotrichum citrinumColletotrichum gloeosporioides PenzApplication in prevention and treatment.
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| CN108299364A (en) * | 2018-02-06 | 2018-07-20 | 常州大学 | A kind of synthetic method of 2- methylols chromanone |
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| CN109574972A (en) * | 2018-07-13 | 2019-04-05 | 郑州大学 | A kind of 3- alkyl substitution -4- chromanone compound and preparation method thereof |
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| CN108299364A (en) * | 2018-02-06 | 2018-07-20 | 常州大学 | A kind of synthetic method of 2- methylols chromanone |
| CN108409699A (en) * | 2018-03-22 | 2018-08-17 | 常州大学 | A kind of synthetic method of 2- alkyl substitution chroman ketone compound |
| CN109574972A (en) * | 2018-07-13 | 2019-04-05 | 郑州大学 | A kind of 3- alkyl substitution -4- chromanone compound and preparation method thereof |
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| Copper-Catalyzed α-Aminoxylation of Ketones with 2,2,6,6-Tetra- methylpiperidine-1-oxyl (TEMPO);Ye-Xiane Xie et al.;《Advanced Synthesis ＆ Catalysis》;20131114;第3387–3390页 * |
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