Method for synthesizing indenone-2-phosphonate derivative

A technology of phosphonate and derivatives, which is applied in the field of phosphonate preparation, can solve the problems of demand, limited range of substrate selection, and expensive catalyst, and achieve the effects of wide application range, low price, and easy operation

Inactive Publication Date: 2009-08-05
SUZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The disadvantages of the above method are: 1, the catalyst used is expensive; 2, the substrate selection range is small; 3, the two substituents of the non-terminal alkyne must be the same, otherwise the generated product is a mixture
[0011] The defect of above method is: 1. Can not synthesize the indanone derivative with substituent in 2 positions; 2. Reaction needs superacid
[0012] In summary, the above two methods cannot synthesize indanone-2-phosphonate derivatives, and these two methods have their own defects and limitations, so the development of new, mild and economical synthetic method is very important
So far, there is no report on the synthesis of indanone-2-phosphonate derivatives

Method used

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  • Method for synthesizing indenone-2-phosphonate derivative
  • Method for synthesizing indenone-2-phosphonate derivative
  • Method for synthesizing indenone-2-phosphonate derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0041] This example is the synthesis of 3-phenylindanone-2-phosphonic acid methyl ester. Using 1,3-diphenylpropynyl ketone and dimethyl phosphite as raw materials, the reaction formula is as follows:

[0042]

[0043] Experimental steps:

[0044] (1) Put 0.206 g (1 mmol) of 1,3-diphenylpropynyl ketone and 0.81 g (3 mmol) of manganese acetate in a round bottom flask, add 20 mL of acetic acid, heat to 80 ° C, and then add dimethyl phosphite 0.220 grams (2mmol), TLC tracking reaction until the end;

[0045] (2) Rotary evaporation removes acetic acid, adds acetone, filters;

[0046] (3) The residue after the filtrate was concentrated was separated by chromatographic column to obtain the target product (yield 74%).

[0047] Product NMR data: 1 H NMR (400MHz, CDCl 3 ): δ 3.65 (d, 6H, 3 J PH =11.4Hz, 2CH 3 ), 7.15-7.17 (m, 1H, ArH), 7.41-7.44 (m, 2H, ArH), 7.53-7.54 (m, 3H, ArH), 7.60-7.63 (m, 3H, ArH). 13C NMR (100MHz, CDCl 3 ): δ 53.1(d, 2 J P-C =5.7Hz), 121.5(d, 1 ...

Embodiment 2

[0049] This example is the synthesis of 3-phenyl-6-nitroindanone-2-phosphonic acid methyl ester. With 1-(3-nitrophenyl)-3-phenylpropynone and dimethyl phosphite as raw materials, the reaction formula is as follows:

[0050]

[0051] Experimental steps:

[0052] (1) Put 1mmol of 1-(3-nitrophenyl)-3-phenylpropynone and 2mmol of manganese acetate in a round bottom flask, add 20mL of acetonitrile, heat to 90°C, then add dimethyl phosphite 1.5mmol, TLC tracking reaction until the end;

[0053] (2) Rotary evaporation removes acetonitrile, adds acetone, filters;

[0054] (3) The residue after the filtrate was concentrated was separated by chromatographic column to obtain the target product (yield 68%).

Embodiment 3

[0056] This example is the synthesis of 3-phenyl-7-bromoindanone-2-phosphonic acid methyl ester. With 1-(2-bromophenyl)-3-phenylpropynone and dimethyl phosphite as raw materials, the reaction formula is as follows:

[0057]

[0058] Experimental steps:

[0059] (1) Put 1mmol of 1-(2-bromophenyl)-3-phenylpropynone and 2.5mmol of manganese acetate in a round bottom flask, add 20mL of ethanol, heat to 30°C, and then add dimethyl phosphite 2mmol, TLC tracking reaction until the end;

[0060] (2) rotary evaporation removes ethanol, adds acetone, filters;

[0061] (3) The residue after the filtrate was concentrated was separated by chromatographic column to obtain the target product (yield 64%).

[0062] Product NMR data: 1 H NMR (400MHz, CDCl 3 ): δ 3.67 (d, 6H, 3 J PH =11.4Hz, 2CH 3 ), 7.10-7.29 (m, 2H, ArH), 7.53-7.58 (m, 6H, ArH); 13 C NMR (100MHz, CDCl 3 ): δ 53.2(d, 2 J P-C =5.9Hz), 119.8, 122.5(d, 1 J P-C =201.9Hz), 123.1, 128.1(d, 3 J P-C = 10.9Hz), 128.5,...

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Abstract

The invention discloses a method for preparing indenone-2-phosphonate derivatives. One of 1, 3-disubstituted propiolic ketone and phosphite ester are taken as reactants, are dissolved into a solvent, and react at a temperature of between 20 and 120 DEG C under the action of manganese acetate to obtain the indenone-2-phosphonate derivatives. The method has the advantages that the method has wide range of applicable substrates, simple and convenient operation, mild conditions, and low production cost, and is suitable for mass production.

Description

technical field [0001] The invention relates to a method for preparing phosphonate, in particular to a method for synthesizing indanone-2-phosphonate derivatives. Background technique [0002] Indanone structures widely exist in natural products and have a wide range of physiological activities. It can also be used as a starting material to synthesize other molecules with physiological activity, such as high C, D ring steroid system, gibberellin, 2,4 or 3,4 substituted 1-naphthol, etc. An important raw material for color-changing indanone oxides, dihydroindanones and indenes. Indanones can be used as alcohol fermentation catalysts, fungicides, and potential estrogen receptors. [0003] So far there is no synthetic report of indanone-2-phosphonate derivatives in the literature (the general formula of indanone-2-phosphonate is as follows: [0004] Only some other indanone derivatives were synthesized. Its synthesis method can be summarized into the following two categori...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40
Inventor 邹建平张广亮周军
Owner SUZHOU UNIV
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