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Method for preparing (E)-2-aryl vinyl phosphonate derivatives

A technology of aryl vinyl phosphonate and aryl vinyl, which is applied in the field of preparation of organic compounds, can solve the problems of high cost, narrow application range of substrates, difficult operation, etc., achieve high raw material utilization rate and reduce reaction waste Production and emission, high catalytic efficiency

Active Publication Date: 2015-01-14
江苏强盛功能化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Aryl vinyl phosphonates are very useful, but the existing preparation methods have the disadvantages of high cost, narrow substrate application range, and difficult operation

Method used

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  • Method for preparing (E)-2-aryl vinyl phosphonate derivatives
  • Method for preparing (E)-2-aryl vinyl phosphonate derivatives
  • Method for preparing (E)-2-aryl vinyl phosphonate derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment one: ( E )-Synthesis of methyl 2-styryl phosphonate

[0038] With 1-nitro-2-styrene, dimethyl phosphite as raw materials, the reaction steps are as follows:

[0039] Add 0.073 g (0.5 mmol) of 1-nitro-2-styrene, 0.057 g (0.5 mmol) of dimethyl phosphite, 0.135 g (0.5 mmol) of manganese acetate, and 0.005 g (0.025 mmol) of copper acetate into the reaction flask. ) and 30 milliliters of methanol, reacted at 60 °C; TLC followed the reaction until it was completely over; the crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate=4:1), and the target product (yield 63% ). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ) : δ 7.69 – 7.32 (m, 6H), 6.20 (t, J = 17.6 Hz, 1H), 3.76 (d, J = 11.2 Hz, 6H).

Embodiment 2

[0040] Embodiment two: ( E )-Synthesis of ethyl 2-styryl phosphonate

[0041]Using 1-nitro-2-styrene and diethyl phosphite as raw materials, the reaction steps are as follows: add 0.073 g (0.5 mmol) of 1-nitro-2-styrene and diethyl phosphite to the reaction flask 0.069 g (0.5 mmol), 0.20 g (0.75 mmol) of manganese acetate, 0.005 g (0.025 mmol) of copper acetate and 30 ml of methanol were reacted at 60°C; TLC followed the reaction until it was completely completed; Analysis and separation (petroleum ether: ethyl acetate=4:1) to obtain the target product (yield 80%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ) : δ 7.68 – 7.35 (m, 6H), 6.19 (t, J = 17.6 Hz, 1H), 4.06 (m, 4H), 1.28 (t, J = 7.1 Hz, 6H).

[0042] by( E )-2-ethyl styryl phosphonate as raw material to synthesize 1-amino-2-phenylethyl phosphonic acid, the reaction steps are as follows:

[0043] (1) Add ( E )-ethyl 2-styrylphosphonate (0.24 g, 1 mmol), ammonia water (0.35 g...

Embodiment 3

[0047] Embodiment three: ( E )-Synthesis of isopropyl 2-styryl phosphonate

[0048] With 1-nitro-2-styrene and diisopropyl phosphite as raw materials, the reaction steps are as follows:

[0049] Add 0.073 g (0.5 mmol) of 1-nitro-2-styrene, 0.12 g (0.75 mmol) of diisopropyl phosphite, 0.20 g (0.75 mmol) of manganese acetate, and 0.005 g (0.025 mmol) of copper acetate into the reaction flask. ) and 30 milliliters of methanol, reacted at 60°C; TLC followed the reaction until it was completely over; the crude product obtained after the reaction was separated by column chromatography (petroleum ether:ethyl acetate=4:1), and the target product (yield 82% ). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ) : δ 7.70 – 7.40 (m, 6H), 6.21 (t, J = 17.6 Hz, 1H), 4.75-4.70 (m, 2H), 1.27 (m, 12H).

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Abstract

The invention discloses method for preparing (E)-2-aryl vinyl phosphonate derivatives. The method comprises the specific following steps of dissolving 1-nitro-2-aryl-vinyl derivatives, a phosphorus reagent, an accelerator manganese acetate and a catalyst copper acetate in a solvent and reacting at 20-100 DEG C to obtain the (E)-2-aryl vinyl phosphonate derivatives. According to the method disclosed by the invention, the 1-nitro-2-aryl-vinyl derivatives are adopted as starting materials, the raw materials are easily available and have multiple varieties; the products obtained by the method disclosed by the invention are multiple and can be directly applied and can be also used for other further reaction; according to the method, the use of precious metal reagents and other additives is avoided; and meanwhile, the synthetic route is short, reaction conditions are mild, the reaction operation and post-treatment process are simple, the yield is high and the method is suitable for scale production.

Description

technical field [0001] The present invention relates to a kind of preparation method of phosphonate derivative, be specifically related to a kind of ( E The invention discloses a preparation method of )-2-aryl vinyl phosphonate derivatives, belonging to the technical field of preparation of organic compounds. Background technique [0002] Alkenyl phosphonate is an important raw material for the synthesis of a-aminophosphonate and a-aminophosphonic acid. The structure of a-aminophosphonic acid is similar to a-amino acid, they are antagonists of a-amino acid, they compete with amino acid for the action site, so they have a wide range of physiological activities such as antibacterial, antiviral, anticancer, pain relief, blood pressure regulation, It can regulate plant growth and other functions, so it can be used as antibacterial agent, anticancer drug, medicine and pesticide. Vinyl phosphonates containing aryl groups can be used to obtain aminoarylethylphosphonic acid, which...

Claims

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Application Information

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IPC IPC(8): C07F9/40
Inventor 邹建平薛剑飞刘业业周少方
Owner 江苏强盛功能化学股份有限公司
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