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A kind of preparation method of allyl thio or selenophosphate and phosphonate

A technology of selenophosphorous ester and allyl sulfur, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve problems such as no one reported, and achieve substrate adaptability Strong, responsive effect

Active Publication Date: 2020-10-02
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports on efficient and green methods for preparing allylthio(seleno)phosphine(phosphate)esters.

Method used

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  • A kind of preparation method of allyl thio or selenophosphate and phosphonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation method of S-allyl diphenyl phosphonothioate comprises the following steps:

[0023] Weigh 0.33mmol diphenylthiophosphonic acid and 0.3mmol cinnamyl alcohol into a test tube, then add 0.3mmol p-TSA . h 2 O, seal the test tube, and carry out a stirring reaction at 30° C. for 1 h to obtain a reaction solution.

[0024] The obtained reaction solution was first dissolved in ethyl acetate, then washed with saturated brine, the organic phase was collected, dried and concentrated, and ethyl acetate / petroleum ether = 1 / 3 (v / v) was used as a developing solvent to analyze the concentrate Separation by column chromatography gave 81.9 mg of the target product.

[0025] The target product yield of this embodiment is 78%.

[0026] NMR characterization was carried out on the target product, the results are as follows: 1 H NMR (500MHz, CDCl 3 ):δ7.89(dd,J=12.9,7.3Hz,4H),7.49-7.47(m,2H),7.46-7.41(m,4H),7.25-7.22(m,2H),7.20-7.17(m ,3H),6.37(d,J=15.6Hz,1H),6.07(dt,J=1...

Embodiment 2

[0028] S-allyl O, the preparation method of O-diethyl phosphorothioate comprises the following steps:

[0029] Weigh 0.3mmol O, O-diethyl S-hydrothiophosphoric acid, 0.33mmol cinnamyl alcohol in a test tube, then add 0.3mmol p-TSA . h 2 O, seal the test tube, and carry out a stirring reaction at 30° C. for 1 h to obtain a reaction solution.

[0030] The obtained reaction solution was first dissolved in ethyl acetate, then washed with saturated brine, the organic phase was collected, dried and concentrated, and ethyl acetate / petroleum ether = 1 / 3 (v / v) was used as a developing solvent to analyze the concentrate Separation by column chromatography gave 69.6 mg of the target product.

[0031] The target product yield of this embodiment is 82%.

[0032] NMR characterization was carried out on the target product, the results are as follows: 1 H NMR (500MHz, CDCl3): δ7.34(d, J=7.5Hz, 2H), 7.29(t, J=7.5Hz, 2H), 7.22(t, J=7.2Hz, 1H), 6.57(d, J=15.7Hz, 1H), 6.25(dt, J=15.3, 7.5Hz,...

Embodiment 3

[0034] S-allyl O, the preparation method of O-diisopropyl phosphorothioate comprises the following steps:

[0035] Weigh 0.3mmol O, O-diisopropylthiophosphonic acid and 0.3mmol cinnamyl alcohol in a test tube, then add 0.33mmolp-TSA . h 2 O, seal the test tube, and carry out a stirring reaction at 30° C. for 1 h to obtain a reaction solution.

[0036] The obtained reaction solution was first dissolved in ethyl acetate, then washed with saturated brine, the organic phase was collected, dried and concentrated, and ethyl acetate / petroleum ether = 1 / 3 (v / v) was used as a developing solvent to analyze the concentrate Separation by column chromatography gave 82.8 mg of the target product.

[0037] The target product yield of this embodiment is 88%.

[0038] NMR characterization was carried out on the target product, the results are as follows: 1 H NMR (500MHz, CDCl 3 ): δ7.36(d, J=7.3Hz, 2H), 7.30(t, J=7.5Hz, 2H), 7.23(t, J=7.2Hz, 1H), 6.59(d, J=15.6Hz, 1H ), 6.27(dt, J=15.4, ...

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Abstract

The invention discloses a preparation method of allyl thiophosphate or selenophosphate and allyl thiophosphonate or selenophosphonate. The preparation method comprises the following specific steps: 1), mixing cinnamyl alcohol and a sulfur reagent or a selenium reagent, then adding TsOH.H2O, and reacting for 1-3 hours at the temperature of 20-40 DEG C to obtain a crude product, wherein the sulfur reagent is thiophosphoric acid or thiohypophosphorous acid and the selenium reagent is selenophosphoric acid or selenohypophosphorous acid; 2), separating and purifying the crude product obtained in the step 1) to obtain the allyl thiophosphate or selenophosphate, or allyl thiophosphonate or selenophosphonate. By the preparation method, use of an organic solvent and a metal catalyst is avoided; thepreparation method has the characteristics of rapid reaction, strong adaptability to a substrate, and high atomic economy and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of allylthio or selenophosphoric acid ester and phosphonic acid ester. Background technique [0002] Allyl-containing compounds are widely found in various compounds, and they are a wide variety of compounds that exist widely in nature. They are important structural units in many natural and biomolecular skeletons with biological activity, and it has been proven It is an important synthetic intermediate and has played an important role in drug synthesis. Therefore, in this context, the synthesis of allyl compounds has become a research hotspot by avoiding unnecessary functionalization operations guided by the principles of green chemistry. Allylthio(seleno)phosphine(phosphate) esters are a class of compounds that have been proven to have good bactericidal and insecticidal activities, and have great medicinal value. However, no one has ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/32C07F9/17C07F9/40C07F9/6574
CPCC07F9/17C07F9/3229C07F9/3258C07F9/4021C07F9/4075C07F9/657181
Inventor 李亮王紫豪潘安健邵长伟宋翔贾一鑫张兴华
Owner SHANGHAI INST OF TECH
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