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Method for efficiently preparing beta-carboxyl phosphate

A technology of carbonyl phosphate and phosphite, which is applied in the field of efficient preparation of β-carbonyl phosphate, and achieves the effects of simple operation, high product yield and mild reaction conditions

Active Publication Date: 2015-04-08
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, no example has been reported for the synthesis of β-carbonyl phosphates from readily available alkynes or alkyne carboxylic acids in the presence of molecular oxygen.

Method used

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  • Method for efficiently preparing beta-carboxyl phosphate
  • Method for efficiently preparing beta-carboxyl phosphate
  • Method for efficiently preparing beta-carboxyl phosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Phenylacetylene (0.5mmol), diethyl phosphite (2mmol), CuOTf (10mol%)

[0025] FeCl 3 (5mol%) was added into a solvent storage bottle containing DMSO (0.5M), Et3N (0.5mmol), then flushed into oxygen (air bag) and sealed, and stirred at 60°C for 24h;

[0026] (2) After the reaction is complete, add ethyl acetate (20ml), wash with deionized water (15ml*2), saturated brine (20ml), combine the organic phases and dry with anhydrous sodium sulfate;

[0027] (3) The organic solvent was evaporated to dryness by a rotary evaporator, and then the product was purified with a silica gel column to obtain β-carbonyl phosphate with a GC yield of 28%.

Embodiment 2

[0029] (1) Phenylacetylene (0.5mmol), diethyl phosphite (2mmol), CuOTf (10mol%)

[0030] FeBr 3 (5mol%) was added into a solvent storage bottle containing DMSO (0.5M), Et3N (0.5mmol), then flushed into oxygen (air bag) and sealed, and stirred at 60°C for 24h;

[0031] Steps (2) and (3) are the same as in Example 1, and the GC yield of the product β-carbonyl phosphate is 26%.

Embodiment 3

[0033] (1) Phenylacetylene (0.5mmol), diethyl phosphite (2mmol), CuOTf (10mol%)

[0034] FeBr 2 (5mol%) was added into the solvent storage bottle containing DMSO (0.5M), Et3N (0.5mmol), then flushed into oxygen (air bag) and sealed, after stirring at 60°C for 24h;

[0035] Steps (2) and (3) are the same as in Example 1, and the GC yield of the product β-carbonyl phosphate is 11%.

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Abstract

The invention discloses a method for synthesizing beta-carboxyl phosphate from alkyne or alkynyl carboxylic compounds and phosphite ester in the presence of copper / iron salt serving as catalysts and molecular oxygen serving as an oxidant. According to the method, multifunctional beta-carboxyl phosphate is obtained by virtue of a novel method having wide substrate range in the presence of the inexpensive catalysts (copper salts and iron salts) in oxygen, which is in a sharp contrast with previously reported view that alkyne cannot act in the presence of molecular oxygen. The method disclosed by the invention has the advantages of mild reaction conditions, easily available raw materials, good compatibility with various reactants, strong practicality and high yield and can be widely applied to various functional reactions.

Description

technical field [0001] The invention relates to a chemical synthesis method, in particular to a method for efficiently preparing β-carbonyl phosphate. Background technique [0002] β-carbonyl phosphates are a very useful class of carbonyl-containing organic compounds, since some β-carbonyl phosphates retain interesting biological activities, and it is the well-known HWE reaction for the construction of α,β-unsaturated Key intermediates of carbonyl compounds and useful universal prerequisites in various synthetic reactions. Due to the diversification and structural manipulation of carbonyl-containing organic compounds, which play a huge role in synthetic reactions, the diverse structures of carbonyl-containing organic compounds are a long-standing theme of organic chemistry. So far, no example has been reported for the synthesis of β-carbonyl phosphates from readily available alkynes or alkyne carboxylic acids in the presence of molecular oxygen. Contents of the invention ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40
Inventor 宋秋玲周明欣
Owner HUAQIAO UNIVERSITY
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