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Method for synthesis of organo-phosphines acid ester derivant

A technology of derivatives and phosphonates, applied in the field of synthesizing organic phosphonate derivatives, can solve the problems of poor method selectivity, poor selectivity, rare raw materials, etc., and achieve the effects of mild reaction conditions, improved selectivity and good selectivity

Inactive Publication Date: 2009-01-14
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] (1) The reaction selectivity is poor, and the selectivity for the two positions of the double bond or the triple bond is poor;
[0016] (2) The substrate range of the reactant is small, and the double bond added is an electron-rich system, and there is no double bond involving an electron-deficient conjugated system;
[0018] Thereby, the method selectivity of prior art is poor, and product purification is difficult; And method one can only synthesize saturated phosphonate derivative; Although method two can synthesize unsaturated phosphonate derivative, raw material (alkyne) is rare, expensive

Method used

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  • Method for synthesis of organo-phosphines acid ester derivant
  • Method for synthesis of organo-phosphines acid ester derivant
  • Method for synthesis of organo-phosphines acid ester derivant

Examples

Experimental program
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Effect test

Embodiment 1

[0045] This example is the synthesis of 1,3-diphenyl-2-propen-1-one-2-phosphonic acid diethyl ester. With 1,3-diphenyl-2-propen-1-one and diethyl phosphite as raw materials, the reaction formula is as follows:

[0046]

[0047] The preparation method is:

[0048] (1) Add 1mmol of 1,3-diphenyl-2-propen-1-one, 2mmol of diethyl phosphite, 5mL of acetic acid, and 3mmol of manganese (III) acetate in a 25mL round-bottomed flask, at 80 Stir at ℃ for 1-2 hours;

[0049] (2) TLC tracking reaction until complete completion;

[0050] (3) column chromatography separation after the end of the reaction, the target product was obtained with a yield of 73%;

[0051] The product is analyzed, the data are as follows:

[0052] H NMR spectrum (400MHz, CDCl 3 ): δ7.87-7.85 (d, 2H, ArH), 7.73 (d, 1H, J P-H =25.7Hz, CH), 7.40-7.09(m, 8H, ArH), 4.06(m, 4H, OC H 2 CH 3 ×2), 1.16(t, 6H, 3 J H-H =5.7, OCH 2 C H 3 ×2);

[0053] C NMR spectrum (100MHz, CDCl 3 ): δ190.5(d, 2 J C-P ...

Embodiment 2

[0056] This example is the synthesis of 1-(4-methoxy)phenyl-3-phenyl-2-propen-1-one-2-phosphonic acid diethyl ester. Using 1-(4-methoxy)phenyl-3-phenyl-2-propen-1-one and diethyl phosphite as raw materials, the reaction formula is as follows:

[0057]

[0058] The preparation method is:

[0059] (1) In a 25mL round bottom flask, add 1mmol of 1-(4-methoxy)phenyl-3-phenyl-2-propen-1-one, 2mmol of diethyl phosphite, 5mL of acetic acid, 3mmol of manganese (III) acetate, stirred at 80°C for 1-2 hours;

[0060] (2) TLC tracking reaction until complete completion;

[0061] (3) Column chromatography separation after the reaction was completed, and the target product was obtained with a yield of 78%;

[0062] The product is analyzed, the data are as follows:

[0063] H NMR spectrum (400MHz, CDCl 3 ): δ7.90(d, 2H, ArH), 7.73(d, 1H, 3 J P-H =26.1Hz, CH), 7.28(d, 2H, ArH), 7.19(m, 3H, ArH), 6.81(d, 2H, ArH), 4.12(m, 4H, OCH 2 ×2), 3.78(s, 3H, CH 3 ), 1.24(t, 6H, 3 J H-H = 6....

Embodiment 3

[0067] This example is the synthesis of 1,3-bis(4-methoxy)phenyl-2-propen-1-one-2-phosphonic acid diethyl ester. With 1,3-bis(4-methoxy)phenyl-2-propen-1-one and diethyl phosphite as raw materials, the reaction formula is as follows:

[0068]

[0069] The preparation method is:

[0070] (1) Add 1mmol of 1,3-bis(4-methoxy)phenyl-2-propen-1-one, 2mmol of diethyl phosphite, 5mL of acetic acid, and 3mmol of manganese acetate in a 25mL round bottom flask. (III), stirring at 80° C. for 1-2 hours;

[0071] (2) TLC tracking reaction until complete completion;

[0072] (3) column chromatography separation after the end of the reaction, the target product was obtained with a yield of 76%;

[0073] The product is analyzed, the data are as follows:

[0074] H NMR spectrum (400MHz, CDCl 3 ): δ7.90(d, 2H, ArH), 7.65(d, 1H, 3 J P-H =25.5Hz, CH), 7.24(d, 2H, ArH), 6.80(d, 2H, ArH), 6.66(d, 2H, ArH), 4.09(m, 4H, OCH 2 ×2), 3.77(s, 3H, CH 3 ), 3.67 (s, 3H, CH 3 ), 1.21(t, 6H, 3 J ...

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Abstract

The invention discloses a method for synthesizing phosphonate ester derivates, comprising: taking one of phosphorous acid esters and one of styrene derivates as reactants, trivalent manganese acetate as a radical initiator, and acetic acid as a solvent, and preparing the phosphonate ester derivates through the reaction at a temperature of between 70 and 90 DEG C; the method improves the selectivity of addition reaction and increases the yield; and has the advantages of simple operation and mild reaction conditions additionally; meanwhile, substrates of the reactants are various, resulting in the diversity of novel structures of phosphonate ester derivates.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing organic phosphonate derivatives. Background technique [0002] Organophosphine compounds widely exist in nature, have strong physiological activity, and are widely used in medicine and agricultural chemistry. Organic phosphonate belongs to organic phosphine compounds, which itself has important physiological activity, and it is also an important intermediate for the synthesis of other biologically active compounds. [0003] In the prior art, the synthesis of phosphonate derivatives is generally through Arbuzov reaction, transition metal catalysis, acid-base catalyzed addition reaction of P-H bond to unsaturated bond, radical-induced addition reaction of P-H bond to unsaturated bond, etc. [0004] At present, the reports of free radicals triggering the addition of P-H bonds to unsaturated bonds include: [0005] (1) The work of Stiles et al. published i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40
Inventor 邹建平潘向强
Owner SUZHOU UNIV
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