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Fluoric alpha-aminoalkyl phosphonate with agricultural antiviral activity and its synthesis

A technology of aminoalkylphosphonate and trifluoromethyl, which is applied in the field of fluorine-containing α-aminoalkylphosphonate with agricultural anti-plant virus activity and the field of synthesis thereof

Inactive Publication Date: 2003-07-30
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And fluorine-containing α-amino alkyl phosphonate compound and its synthetic method have no report both at home and abroad

Method used

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  • Fluoric alpha-aminoalkyl phosphonate with agricultural antiviral activity and its synthesis
  • Fluoric alpha-aminoalkyl phosphonate with agricultural antiviral activity and its synthesis

Examples

Experimental program
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Embodiment (1

[0063] Embodiment (1): The synthesis (I) of compound e is in the 25mL there-necked flask that water separation reflux device and thermometer are housed, add p-trifluoromethylaniline 5.3mmol, 15mL toluene, after stirring and dissolving, add 5.3mmol p-trifluoromethylaniline Chlorobenzaldehyde, heated and refluxed for 1h, cooled to room temperature, the solution was turbid and strong, evaporated toluene, and recrystallized three times with ethanol to obtain a light yellow solid.

[0064] (II), O, the synthesis of O-diethyl phosphite is in the 500ml four-neck bottle that drying tube, nitrogen protection device, gas absorption device and constant pressure funnel are housed, add 75ml carbon tetrachloride and 1.8mol nitric acid Water and ethanol, under ice-water bath cooling, slowly add 0.51mol PCl3 dissolved in 50ml carbon tetrachloride dropwise, control the dropwise addition in 1.5-2 hours; slowly raise the temperature to 70°C and react for 1 hour, the solution changes from colorles...

Embodiment (2

[0066] Embodiment (2): the synthesis (I) of compound f is in the 25mL there-necked flask that water separation reflux device and thermometer are housed, add p-trifluoromethylaniline 5.3mmol, 15mL toluene, after stirring and dissolving, add 5.3mmol o Fluorobenzaldehyde, heated and refluxed for 1.5h, cooled to room temperature, the solution was turbid and strong, evaporated toluene, and recrystallized three times with ethanol to obtain a light yellow solid.

[0067] (II), O, the synthesis of O-diethyl phosphite is in the 500ml four-neck bottle that drying tube, gas absorption device, nitrogen protection device and constant pressure funnel are housed, add 75ml carbon tetrachloride and 1.8mol nitric acid Water and ethanol, under ice-water bath cooling, slowly add 0.51mol PCl3 dissolved in 50ml carbon tetrachloride dropwise, control the dropwise addition in 1.5-2 hours; slowly raise the temperature to 70°C and react for 1 hour, the solution changes from colorless to light Yellow, u...

Embodiment (3

[0069] Embodiment (3): The synthesis (I) of compound c is in the 25mL there-necked flask that water separation reflux device and thermometer are housed, add p-trifluoromethylaniline 5.3mmol, 15mL toluene, after stirring and dissolving, add 5.3mmol p-trifluoromethylaniline Fluorobenzaldehyde, heated and refluxed for 1h, cooled to room temperature, the solution was turbid and strong, evaporated toluene, and recrystallized three times with ethanol to obtain a light yellow solid.

[0070](II), O, the synthesis of O-diisopropyl phosphite In the 500ml four-necked bottle that drying tube, gas absorption device and constant pressure funnel are housed, add 75ml carbon tetrachloride and 1.8mol anhydrous isopropyl Alcohol, under cooling in an ice-water bath, slowly add 0.51mol PCl3 dissolved in 50ml of carbon tetrachloride dropwise, and control the dropwise addition in 1.5 hours; slowly raise the temperature to 70°C for 1 hour, and the solution changes from colorless to light yellow, and ...

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Abstract

The present invention relates to fluoric derivative of alpha-aminoalkyl phosphonate compound and its synthesis. Through active group splicing method, fluorine atom is introduced into alpha-aminoalkylphosphonate to synthesize serial fluoric alpha-aminoalkyl phosphate compounds. The synthesis features that substituted aniline, substituted banzaldehyde, anhydrous alcohol and phosphorus trichloride as materials in synthesized through a three-step process into fluoric alpha-aminoalkyl phosphonate compounds in solvent of toluene, benzene, ethanol, methanol, etc. The said derivatives have improved physical and chemical performance, increased liposolubility in organism, membrane permeability, etc.

Description

(1) Technical field [0001] The present invention is a derivative of a fluorine-containing α-aminoalkyl phosphonate compound and a synthesis method thereof. A series of fluorine-containing α- Amino alkyl phosphonate compound, its general structural formula is as follows: [0002] R 1 =H (hydrogen), o-F (ortho fluorine), p-F (para fluorine), p-Cl (para chlorine); [0003] R 2 = CF 3 (trifluoromethyl), CH 3 (methyl), H (hydrogen), NO 2 (nitro); [0004] R 3 = H (hydrogen), NO 2 (nitro); [0005] R = Me (methyl), Et (ethyl), i-Pr (isopropyl), n-Pr (n-propyl), n-Bu (n-butyl). [0006] α-Aminoalkylphosphonate compounds have many important biological activities such as anti-plant virus, inhibition of enzyme activity, anti-tumor, weeding, and bactericidal. The process of the present invention uses active group splicing to introduce fluorine atoms into α-aminoalkyl phosphonate, which can change the physical and chemical properties of the compound, increase the volatility, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/42
Inventor 宋宝安吴扬兰黄荣茂
Owner GUIZHOU UNIV
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