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A kind of synthetic method of trisubstituted phosphine oxide compound

A synthesis method and compound technology, applied in chemical instruments and methods, compounds of elements in group 5/15 of the periodic table, organic chemistry, etc., to achieve the effects of air and water stability, wide application range, and low requirements for reaction conditions

Active Publication Date: 2021-05-28
XINYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has great advantages compared with the traditional method, the alkoxyphosphine reagent is very sensitive to water and air, and it is found that the product of the direct rearrangement of the alkoxyphosphine itself is formed during the reaction.

Method used

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  • A kind of synthetic method of trisubstituted phosphine oxide compound
  • A kind of synthetic method of trisubstituted phosphine oxide compound
  • A kind of synthetic method of trisubstituted phosphine oxide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]Diphenyl oxoslate and benzyl alcohol

[0028]

[0029]Under nitrogen protection, diphenyl oxide (101.0 mg, 0.50 mmol), benzyl alcohol (64.8 mg, 0.60 mmol, 1.2 Equiv.) And trimethyl chloride (5.4 mg, 0.05) were sequentially added to the 10 ml tubular reactor. Mmol, 10 mol%), and then heated to 80 ° C for 12 h under a solvent condition. The product was purified by column chromatography, and the separation yield was 25%.1H NMR (500MHz, CDCL3Δ7.73-7.65 (m, 4H), 7.55-7.38 (M, 6H), 7.21-7.00 (m, 3H), 7.13-7.00 (M, 2H), 3.64 (D, J = 14.4 Hz, 2H) .13C NMR (125MHz, CDCL3Δ132.29 (D, J = 98.9 Hz), 131.91 (D, J = 2.8 Hz), 131.19 (D, J = 9.1 Hz), 130.24 (D, J = 5.2 Hz), 128.61 (D, J = 11.7 Hz), 128.48 (D, J = 2.2 Hz), 126.87 (D, J = 2.9 Hz), 38.17 (D, J = 66.5 Hz).31P NMR (202MHz, CDCL3Δ29.5 (s).

Embodiment 2

[0031]Diphenyl oxoslate and benzyl alcohol

[0032]

[0033]Under nitrogen protection, diphenyl oxide (101.0 mg, 0.50 mmol), benzyl alcohol (64.8 mg, 0.60 mmol, 1.2 equiv.) And trimethyl bromide (7.7 mg, 0.05) were sequentially added to a 10 ml tubular reactor. Mmol, 10 mol%), and then heated to 80 ° C for 12 h under a solvent condition. The product was purified by column chromatography, and the separation yield was 75%.1H NMR (500MHz, CDCL3Δ7.73-7.65 (m, 4H), 7.55-7.38 (M, 6H), 7.21-7.00 (m, 3H), 7.13-7.00 (M, 2H), 3.64 (D, J = 14.4 Hz, 2H) .13C NMR (125MHz, CDCL3Δ132.29 (D, J = 98.9 Hz), 131.91 (D, J = 2.8 Hz), 131.19 (D, J = 9.1 Hz), 130.24 (D, J = 5.2 Hz), 128.61 (D, J = 11.7 Hz), 128.48 (D, J = 2.2 Hz), 126.87 (D, J = 2.9 Hz), 38.17 (D, J = 66.5 Hz).31P NMR (202MHz, CDCL3Δ29.5 (s).

Embodiment 3

[0035]Diphenyl oxoslate and benzyl alcohol

[0036]

[0037]Under nitrogen protection, diphenyl oxosphate (101.0 mg, 0.50 mmol), benzyl alcohol (64.8 mg, 0.60 mmol, 1.2 Equiv.) And trimethyl iodosilane (10.0 mg, 0.05) were sequentially added to a 10 ml tubular reactor. Mmol, 10 mol%), and then heated to 80 ° C for 12 h under a solvent condition. The product was purified by column chromatography, and the separation yield was 95%.1H NMR (500MHz, CDCL3Δ7.73-7.65 (m, 4H), 7.55-7.38 (M, 6H), 7.21-7.00 (m, 3H), 7.13-7.00 (M, 2H), 3.64 (D, J = 14.4 Hz, 2H) .13C NMR (125MHz, CDCL3Δ132.29 (D, J = 98.9 Hz), 131.91 (D, J = 2.8 Hz), 131.19 (D, J = 9.1 Hz), 130.24 (D, J = 5.2 Hz), 128.61 (D, J = 11.7 Hz), 128.48 (D, J = 2.2 Hz), 126.87 (D, J = 2.9 Hz), 38.17 (D, J = 66.5 Hz).31P NMR (202MHz, CDCL3Δ29.5 (s).

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Abstract

The invention provides a method for synthesizing trisubstituted phosphine oxide compounds. The method uses cheap, easy-to-obtain, wide-sourced, stable and low-toxic monohydric alcohol or dihydric alcohol as an alkylating agent, uses cheap and easily available halosilane as a catalyst, and directly obtains a trisubstituted phosphine oxide compound through highly selective reaction. The reaction method is simple, the condition is mild, no solvent is needed, and the operation is easy, and the reaction by-product is water. The method has lower requirements on reaction conditions, can use benzyl type, allyl type and aliphatic alcohols as alkylating reagents, can realize the synthesis of target phosphine oxide compounds, and has a wide application range. This method can also be easily scaled up to 20 times for production, and the gram-level preparation of the product should be carried out, so it should also have certain research and industrial application prospects.

Description

Technical field[0001]The present invention belongs to the field of chemical synthesis, and more particularly to a synthetic method of three-choice phosphine compounds.Background technique[0002]The three-choho-phosphine compound can be more convenient to reduce the three-choice phosphine compound, which can be widely used as a ligand to a transition metal catalytic coupling reaction, asymmetric catalytic synthesis, and three-substituted oxophosphine or three-substituted phosphine compounds can also be Some organic reactions were catalyzed directly as a catalyst. The three-substituted oxophosphine structure is present in natural products and pharmacologically active compounds. Therefore, the synthesis of the three-substituted oxophosphine compound also causes the attachment of organic chemists.[0003]The methods for preparing three-choice phosphine compounds mainly include Albuzov under high temperature conditions by halogenate hydrocarbons and alkoxyphosphosphine, but the reaction nee...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/53C07F9/6553
CPCC07F9/5325C07F9/5333C07F9/655345
Inventor 于静马献涛燕然徐清
Owner XINYANG NORMAL UNIVERSITY