Phosphate compound, and preparation method and application thereof

A technology of phosphate esters and compounds, which is applied in the field of phosphate ester compounds and their preparation, can solve the problems of low yield, low energy consumption, and large energy consumption, and achieve low waste discharge, high yield, and reaction equipment simple effect

Pending Publication Date: 2020-08-21
GUANGDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The technical problem to be solved by the present invention is to overcome the defects and deficiencies that the preparation of existing phosphoric acid ester compounds requires the use of toxic salts as catalysts, high temperature conditions, high energy consumption, and low yield, and provide a phosphoric acid ester compound, This type of new compound is prepared by phosphine oxide compound and hydroxyl substituted organic matter under the joint catalysis of alkali and halogenated substance through nucleophilic substitution reaction. The reaction catalyst is non-toxic, mild condition, low energy consumption, high yield, and Further enrich the library of phosphate compounds, providing more options for the research of its synthetic drugs

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  • Phosphate compound, and preparation method and application thereof
  • Phosphate compound, and preparation method and application thereof
  • Phosphate compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] A phosphate ester compound is 3,4-dimethoxyphenyl diphenylphosphinate, which has a molecular structure as shown in formula (II):

[0057] The preparation method of above-mentioned formula (II) compound, comprises the steps:

[0058] Take a 15mL pressure-resistant reaction tube, add 61mg of diphenylphosphine oxide, 231mg of 3,4-dimethoxyphenol, 36mg of chloroform, 69mg of 1,8-diazabicycloundec-7-ene (DBU), Acetonitrile 2mL, open reaction, stirred at room temperature for 3h. After the reaction was completed, 10 mL of ethyl acetate was added to quench the reaction, washed with 10 mL of saturated sodium sulfate solution, the organic phase was separated, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, and separated by column chromatography to obtain 3,4-dimethyl Pure oxyphenyl diphenyl phosphinate (colorless oil) 101 mg, yield 95%; wherein the molar ratio of diphenyl phosphine oxide to 3,4-dimethoxyphenol is 1:5, The mola...

Embodiment 2

[0068] A phosphate ester compound is 2,3-dihydroxypropyl diphenylphosphinate, which has a molecular structure as shown in formula (III):

[0069] The preparation method of the above-mentioned compound of formula (III) is the same as in Example 1, except that 231 mg of 3,4-dimethoxyphenol is replaced by 138 mg of glycerol to obtain 2,3-dihydroxypropyldiphenylene 85 mg of pure phosphonate, yield 96%; wherein the molar ratio of diphenylphosphine oxide to glycerin is 1:5, the molar ratio of diphenylphosphine oxide to chloroform is 1:1, and the molar ratio of diphenylphosphine oxide to chloroform is 1:1. The DBU molar ratio is 1:1.5.

[0070] The NMR results of the above-mentioned formula (Ⅲ) compound are as follows: Figure 4 , 1 H NMR (400MHz, CDCl 3 )δ7.85–7.75(m,4H),7.60–7.51(m,2H),7.50–7.41(m,4H),4.11(dd,J=11.0,5.0Hz,2H),3.95(p,J= 4.8Hz, 1H), 3.71(d, J=4.7Hz, 2H).

[0071] From Figure 5 It can be seen that 13 C NMR (101MHz, CDCl 3 )δ132.95–132.27(m), 131.67(dd, J=10...

Embodiment 3

[0077] A phosphate compound is methyl bis[[1,1'-biphenyl]-4-yl]phosphinate, and the phosphate compound has a molecular structure as shown in formula (IV):

[0078] The preparation method of the above-mentioned compound of formula (IV) is the same as that of Example 1, except that diphenylphosphine oxide is replaced by 106 mg of bis([1,1'-biphenyl]-4-yl)phosphine oxide, 3,4- Dimethoxyphenol was replaced by methanol 48mg, and acetonitrile was replaced by polyethylene glycol 200 2mL to obtain 98mg of pure methyl bis[[1,1'-biphenyl]-4-yl]phosphinate (white solid), The yield is 85%; the molar ratio of bis([1,1'-biphenyl]-4-yl)phosphine oxide to methanol is 1:5, and bis([1,1'-biphenyl]-4-yl) The molar ratio of phosphine oxide to chloroform is 1:1, and the molar ratio of bis([1,1'-biphenyl]-4-yl)phosphine oxide to DBU is 1:1.5.

[0079] The NMR results of the above-mentioned formula (VII) compound are as follows: Figure 7 , 1 H NMR (400MHz, CDCl 3 )δ7.94(dd, J=11.9,8.3Hz,4H),7...

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Abstract

The invention discloses a phosphate compound, and a preparation method and application thereof. The phosphate compound has a molecular structure represented by formula (I); and in the formula (I), R1is one of a phenyl group, a biphenyl group, a fluorophenyl group, a dimethoxy substituted phenyl group and a naphthyl group, R2 is one of a phenyl group, a biphenyl group, a fluorophenyl group, a dimethoxy substituted phenyl group and a naphthyl group, R3 is one of (3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptane-2-yl)hexahydro-1H-cyclopenta[a]phenanthrene-3-yl group, a dimethoxy substituted phenyl group, a 2,3-dihydroxypropyl group and a methyl group, and when R3 is the methyl group, R1 and R2 are not the phenyl group. The phosphate compound is prepared from a phosphine oxide compound and a hydroxyl-substituted organic matter in a certain ratio under mild conditions, is high in yield and can be applied to the field of drug synthesis.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, and more specifically, to a phosphoric acid ester compound and its preparation method and application. Background technique [0002] Phosphate ester compounds have certain drug activity and are widely used in medicine, and can also be used in agriculture to prevent and control various pests and diseases. Chinese patent CN107522741A proposes a phosphoric acid ester compound. The synthesis method of this type of compound is to use alcohol and H-phosphite compound as raw materials, oxygen as an oxidant, divalent cobalt salt and N-hydroxyphthalimide As a co-catalyst, react at 80-110°C for 12-18 hours to prepare phosphoric acid ester compounds, but this preparation method uses toxic cobalt salt as a catalyst, and requires long-term reaction at high temperature, which consumes a lot of energy and has low yield. High, not conducive to energy saving and environmental protection, and also not c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/32C07J51/00
CPCC07F9/3229C07F9/3282C07F9/3264C07J51/00
Inventor 区颖聪陈迁何圳林黄远婷余国典霍延平
Owner GUANGDONG UNIV OF TECH
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