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O, o'-dialkyl-o"-(substituted flavone-3-yl) phosphate derivatives, preparation method and application

A phosphate ester, dimethoxyflavonoid technology, applied in the fields of botanical equipment and methods, chemicals for biological control, applications, etc. The effect of multiple reaction sites

Active Publication Date: 2018-10-23
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] There are relatively few research reports on anti-phytopathogenic bacteria. Flavonols and H-phosphite compounds have so many good biological activities, but there is no introduction of phosphite into the 3-position of flavonol to synthesize a phosphate-containing structure. O, O'-diethyl-O"-(substituted flavonol-3-yl) phosphate lipid compounds, no O, O'-diethyl-O"-( Report on Anti-phytopathogenic Bacteria Activity of Substituted Flavonol-3-yl) Phosphate Lipids

Method used

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  • O, o'-dialkyl-o"-(substituted flavone-3-yl) phosphate derivatives, preparation method and application
  • O, o'-dialkyl-o"-(substituted flavone-3-yl) phosphate derivatives, preparation method and application
  • O, o'-dialkyl-o"-(substituted flavone-3-yl) phosphate derivatives, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] O, the preparation method of O'-diethyl-O "-(4'-fluoro-7-methoxyflavone-3-yl) phosphate ester (compound number is A1), comprises the following steps:

[0044] (1) Preparation of 2-hydroxyl-4-methoxyacetophenone

[0045] Add raw materials 2,4-dihydroxyacetophenone (3.29mmol), 30mL acetonitrile and (4.93mmol) anhydrous potassium carbonate into a 50mL single-necked flask, stir at room temperature for 0.5h, then add iodomethane (3.61mmol), TLC monitoring to the raw material After disappearing, stop the reaction, extract with ethyl acetate, and distill under reduced pressure to obtain a crude product, which is subjected to silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 10: 1] to obtain 2-hydroxy-4-methoxy Acetophenone, yield 90%.

[0046] (2) Preparation of 4-fluoro-2'-hydroxy-4'-methoxychalcone

[0047] Add 30ml of 20% (V / V) ethanol and (11.06mmol) sodium hydroxide in a 50mL single-necked flask, stir at room temperature for 0.5h, then add subst...

Embodiment 2

[0053] O, the preparation method of O'-diethyl-O "-(3'-bromo-7-methoxyflavone-3-yl) phosphate ester (compound number is A2), comprises the following steps:

[0054] (1) Preparation of 2-hydroxyl-4-methoxyacetophenone:

[0055] As in the first (1) step of Example 1.

[0056] (2) Preparation of 3-bromo-2'-hydroxyl-4'-methoxychalcone:

[0057] As in the (2) step of Example 1, the difference is that 3-bromobenzaldehyde is used as a raw material.

[0058] (3) Preparation of 3'-bromo-7-methoxyflavonol:

[0059] As in step (3) of Example 1, the difference is that 3-bromo-2'-hydroxyl-4'-methoxyl group is used as raw material.

[0060] (4) Preparation of O, O'-diethyl-O"-(3'-bromo-7-methoxyflavone-3-yl) phosphate ester:

[0061] As in the (4) step of Example 1, the difference is that 3'-bromo-7-methoxyflavonol is used as a raw material. The yield is 65%, and the melting point is 80-82°C.

Embodiment 3

[0063] O, the preparation method of O'-diethyl-O "-(7-methoxyflavone-3-yl) phospholipid (compound number is A3), comprises the following steps:

[0064] (1) Preparation of 2-hydroxyl-4-methoxyacetophenone:

[0065] As in the first (1) step of Example 1.

[0066] (2) Preparation of 2'-hydroxyl-4'-methoxychalcone:

[0067] As in the (2) step of embodiment 1, the difference is that benzaldehyde is used as a raw material.

[0068] (3) Preparation of 7-methoxyflavonol:

[0069] As in step (3) of Example 1, the difference is that 2'-hydroxyl-4'-methoxychalcone is used as a raw material.

[0070] (4) Preparation of O, O'-diethyl-O"-(7-methoxyflavone-3-yl) phosphate ester:

[0071] As in step (4) of Example 1, the difference is that 7-methoxyflavonol is used as a raw material. Yield 52%, melting point 72-74°C.

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Abstract

The invention discloses an O,O'-dialkyl-O''-(substituted flavone-3-yl)phosphate ester derivative, a preparation method and application. A structural formula (I) of the derivative is as follows, where R1 is hydrogen, an alkyl group and an alkoxy group; R2 is one or more alkyl groups, alkoxy groups and halogen atoms; R3 is an alkyl group; the alkyl groups are C1-C6 alkyl groups, the alkoxy groups are C1-C6 alkoxy groups, and the halogen atoms can be fluorine, chlorine and bromine. The O,O'-dialkyl-O''-(substituted flavone-3-yl)phosphate ester derivative has relatively high plant bacterium resistant activity. (The structural formula (I) is shown in the description.).

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to an O, O'-dialkyl-O"-(substituted flavone-3-yl) phosphate derivative, and also to the O, O'-dialkyl Preparation method of alkyl-O"-(substituted flavonoid-3-yl) phosphate derivatives, and derivatives containing O, O'-dialkyl-O"-(substituted flavone-3-yl) phosphate derivatives The application of substances to inhibit the activity of plant bacteria. Background technique [0002] Flavonols, as secondary metabolites in organisms, are widely distributed in nature, and have attracted extensive attention at home and abroad because of their diverse physiological activities. At present, the biological activity research of flavonol compounds mainly focuses on the cardiovascular system, anti-virus, anti-inflammatory and anti-tumor effects. [0003] H-phosphite contains a strong polar phosphoryl group (P=O), which is an important active group. Its special structure and properties m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/655A01N57/16A01P1/00
CPCA01N57/16C07F9/65522
Inventor 薛伟黄民国王晓斌陈丽娟王一会贺鸣唐显福王岚李普张橙
Owner GUIZHOU UNIV