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Method for electrochemical synthesis of acyl phosphate

An acyl phosphate, electrochemical technology, applied in the field of electrochemical synthesis of acyl phosphate, can solve the problems of poor operability, unfriendly environment, limited reaction substrates, etc., and achieve strong operability, air stability, The effect of simple synthesis process

Active Publication Date: 2020-09-04
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These systems are not friendly to the environment, do not conform to the concept of green chemistry, the step economy is not high, and the reaction substrate is limited and the operability is not strong.

Method used

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  • Method for electrochemical synthesis of acyl phosphate
  • Method for electrochemical synthesis of acyl phosphate
  • Method for electrochemical synthesis of acyl phosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Phosphorylation of p-toluic acid 3a by diethyl phosphite.

[0031] Use p-toluic acid 1a (27.2 mg, 0.2 mmol), diethyl phosphite 2a (77.2 μL, 0.6 mmol), tetrabutylammonium bromide (66.5 mg, 1 equiv.), and platinum electrodes as positive and negative electrodes, respectively , added in 8.0mL of acetonitrile, at room temperature, the system reacted under the condition of a continuous current of 10mA for 6h in an air atmosphere and then stopped the reaction, separated by column chromatography (using a silica gel column; eluent: sherwood oil / ethyl acetate=7 / 1) to obtain the phosphorylated product 3a of p-toluic acid. The product was a colorless liquid with a yield of 90%.

[0032] 1 HNMR (400MHz, CDCl 3 )δ7.87(d, J=7.6Hz, 2H), 7.21(d, J=7.5Hz, 2H), 4.29(p, J=7.2Hz, 4H), 2.36(s, 3H), 1.34(t, J=7.1Hz, 6H). 13 C NMR (101MHz, CDCl 3 )δ162.01(d, J=8.4Hz), 147.62, 132.62, 130.45, 126.35(d, J=8.1Hz), 66.21(d, J=5.9Hz), 22.72, 17.02(d, J=6.6Hz) .

[0033] Its synt...

Embodiment 2

[0035] Example 2: Phosphorylation of benzoic acid by diethyl phosphite 3b.

[0036] Use p-toluic acid 1b (24.4 mg, 0.2 mmol), diethyl phosphite 2a (77.2 μL, 0.6 mmol), tetrabutylammonium bromide (66.5 mg, 1 equiv.), and platinum electrodes as positive and negative electrodes, respectively , added in 8.0mL of acetonitrile, at room temperature, the system reacted under the condition of a continuous current of 10mA for 6h in an air atmosphere and then stopped the reaction, separated by column chromatography (using a silica gel column; eluent: sherwood oil / ethyl acetate=7 / 1), obtain the phosphorylation product 3b of benzoic acid. The product was a colorless liquid with a yield of 85%.

[0037] 1 HNMR (400MHz, CDCl 3 )δ8.09(d, J=7.1Hz, 2H), 7.67(t, J=7.7Hz, 1H), 7.51(t, J=7.9Hz, 2H), 4.51-4.29(m, 4H), 1.45( td, J=7.2, 0.9Hz, 6H). 13 C NMR (101MHz, CDCl 3 )δ160.87(d, J=8.2Hz), 134.45, 130.43, 128.6, 7128.08(d, J=8.3Hz), 65.15(d, J=5.9Hz), 16.02(d, J=6.9Hz).

[0038] Its synt...

Embodiment 3

[0040] Example 3: Phosphorylation of o-toluic acid by diethyl phosphite 3c.

[0041] Use o-toluic acid 1c (27.2 mg, 0.2 mmol), diethyl phosphite 2a (77.2 μL, 0.6 mmol), tetrabutylammonium bromide (66.5 mg, 1 equiv.), and platinum electrodes as positive and negative electrodes, respectively , added in 8.0mL of acetonitrile, at room temperature, the system reacted under the condition of a continuous current of 10mA for 6h in an air atmosphere and then stopped the reaction, separated by column chromatography (using a silica gel column; eluent: sherwood oil / ethyl acetate=7 / 1) to obtain the phosphorylated product 3c of o-toluic acid. The product was a colorless liquid with a yield of 70%.

[0042] 1 HNMR (400MHz, CDCl3 )δ8.01(d, J=7.3Hz, 1H), 7.51(t, J=6.9Hz, 1H), 7.41(d, J=7.2Hz, 2H), 4.56-4.29(m, 4H), 2.67( s, 3H), 1.45 (t, J=6.7Hz, 6H). 13 C NMR (101MHz, CDCl 3 )δ160.91(d, J=8.1Hz), 142.55, 133.69, 132.12, 131.72, 126.62(d, J=7.9Hz), 125.89, 65.12(d, J=5.9Hz), 21.91, 16.05...

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Abstract

The invention discloses a method for electrochemical synthesis of acyl phosphate. Specifically, in an electrochemical reaction system, platinum electrodes are respectively used as a positive electrodeand a negative electrode, a small amount of electrolyte is added, dialkyl phosphite and a derivative thereof are used as phosphoric acid sources, carboxylic acid and a derivative thereof are used asacyl sources, and the system is enabled to react for 6 hours under the condition of a continuous current of 10mA at room temperature; and after the reaction is finished, the solvent is pumped out, andcolumn chromatography separation is carried out according to a volume ratio of petroleum ether to ethyl acetate being 7: 1 to obtain acyl phosphate. According to the method, based on electrochemicalreaction, carboxylic acid and dialkyl phosphite react, acyl phosphate can be obtained in one step, reaction raw materials are stable to air, cheap and easy to obtain, the synthesis process is simple,and the operability is high; the reaction can be carried out without metals and oxidants, and the obtained by-product is hydrogen which is environment-friendly.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for electrochemically synthesizing acyl phosphate. Background technique [0002] Organophosphates exist as building blocks in various common natural products and pesticides, and possess outstanding biological properties. Meanwhile, acyl phosphates are one of the extremely important organic substances, which have been widely used in organic synthesis intermediates, drugs and functional materials. In addition, acyl phosphates are intermediates in many biochemical acylation reactions (C.Queffélec, M.Petit, P.Janvier, D.A.Knight, B.Bujoli, Chem.Rev., 2012, 112, 3777; N.H.Duffy, D.A.Dougherty , Org.Lett., 2010, 12, 3776.) Therefore, the synthesis method of acyl phosphate has attracted people's continuous attention and extensive research. At present, the synthetic methods for realizing acyl phosphate are: [0003] Method 1: Acylation reaction of acid chlo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 郭生梅
Owner NANCHANG UNIV
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