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Method for synthesizing indenone-2-diphenyl sulfide derivatives

A technology for phenylene sulfide and derivatives, which is applied in the field of organic synthesis, can solve the problems of unable to synthesize indanone-2-phenylene sulfide derivatives, unable to synthesize indanone derivatives, expensive catalysts, etc., and achieves mild conditions and easy operation. Simple, Inexpensive Effects

Inactive Publication Date: 2010-08-18
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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 indenone derivative with substituent in 2 positions; 2, reaction needs superacid
[0012] In summary, the above two methods cannot synthesize indanone-2-phenylene sulfide derivatives, and these two methods have their own defects and limitations, so the development of new, mild and economical synthesis method is very important

Method used

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  • Method for synthesizing indenone-2-diphenyl sulfide derivatives
  • Method for synthesizing indenone-2-diphenyl sulfide derivatives
  • Method for synthesizing indenone-2-diphenyl sulfide derivatives

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Embodiment 1

[0043] Embodiment one: the present embodiment is 3-phenylindanone-2-phenylene sulfide (such as figure 1 , R 1 =R 2 =R 3 =R 4 =R 5 =R 6 =H) synthetic; With 1,3-diphenyl propargyl ketone, thiophenol as raw material, its reaction formula is as follows:

[0044]

[0045] Experimental steps:

[0046] (1) Put 0.206 g (1 mmol) of 1,3-diphenylpropynyl ketone and 0.81 g (3 mmol) manganese acetate in a round bottom flask, add 20 mL of acetonitrile, heat to reflux, then add 1.5 mL of thiophenol ( 1.5mmol), TLC tracking reaction until the end. Cool to room temperature, filter;

[0047] (2) rotary evaporation removes acetonitrile;

[0048] (3) The concentrated residue was separated by chromatographic column to obtain the target product (yield 81%).

[0049] Product data: 1 H NMR (400MHz, CDCl 3 ): δ7.61(d, 2H, J=5.5Hz, ArH), 7.55-7.50(m, 4H, ArH), 7.41-7.38(t, 1H, J=7.4Hz, ArH), 7.32-7.28(m , 3H, ArH), 7.23-7.20(t, 3H, J=7.1Hz, ArH), 7.20-7.13(t, 1H, J=7.0Hz, ArH). 13 C NM...

Embodiment 2

[0050] Embodiment Two: This embodiment is the synthesis of 3-phenyl-7-fluoroindanone-2-phenylene sulfide; with 1-(2-fluorophenyl)-3-phenylpropynyl ketone and thiophenol as Raw material, its reaction formula is as follows:

[0051]

[0052] Experimental steps:

[0053] (1) Put 1mmol of 1-(2-fluorophenyl)-3-phenylpropynone and 1.5mmol of manganese acetate in a round bottom flask, add 20mL of ethanol, heat to 30°C, then add 2mL of thiophenol (2mmol), TLC followed the reaction until the end. Cool to room temperature and filter.

[0054] (2) rotary evaporation removes ethanol;

[0055] (3) The concentrated residue was separated by chromatographic column to obtain the target product (yield 46%).

[0056] Product data: 1 H NMR (300MHz, CDCl 3 ): δ7.54 (s, 2H, ArH), 7.50 (d, 3H, J=2.4Hz, ArH), 7.39-7.37 (m, 1H, ArH), 7.28-7.26 (m, 2H, ArH), 7.21 -7.18(m, 3H, ArH), 7.01-6.93(m, 2H, ArH). 13 C NMR (75MHz, CDCl 3 ): 189.5, 160.8-160.7 ( 1 J F-C =4.4Hz), 160.1, 156.5, 146.8,...

Embodiment 3

[0057] Embodiment Three: This embodiment is the synthesis of 3-phenyl-5-chloroindanone-2-phenylene sulfide; with 1-(4-chlorophenyl)-3-phenylpropynyl ketone and thiophenol as Raw material, its reaction formula is as follows:

[0058]

[0059] (1) Put 1 mmol of 1-(4-chlorophenyl)-3-phenylpropynone and 0.41 g (1.5 mmol) of manganese acetate in a round bottom flask, add 20 mL of formic acid, heat to reflux, and then add phenylsulfide Phenol 1.5mL (1.5mmol), TLC tracking reaction until the end. Cool to room temperature and filter.

[0060] (2) rotary evaporation removes formic acid;

[0061] (3) The concentrated residue was separated by chromatographic column to obtain the target product (yield 78%).

[0062] Product data: 1 H NMR (300MHz, CDCl 3 ): δ7.56-7.53 (m, 2H, ArH), 7.51-7.49 (dd, 3H, J 1 =1.9Hz,J 2 =5.0Hz, ArH), 7.44(d, 1H, J=7.7Hz, ArH), 7.29-7.23(m, 3H, ArH), 7.21(s, 1H, ArH), 7.17-7.15(m, 3H, ArH ). 13 C NMR (100MHz, CDCl 3 ): 193.7, 160.0, 139.9, 134.9, 13...

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Abstract

The invention belongs to the field of organic synthesis, and relates to a preparation method of indenone, particularly a method for synthesizing indenone-2-diphenyl sulfide derivatives. The method comprises the following steps: using 1,3-disubstituted allylene ketone and thiophenol as the reactants, dissolving the reactants in a solvent at 20-120 DEG C, and reacting under the action of manganese acetate to prepare the indenone-2-diphenyl sulfide derivatives, wherein the mol ratio of 1,3-disubstituted allylene ketone to thiophenol is less than or equal to 1:2, and the mol ratio of 1,3-disubstituted allylene ketone to manganese acetate is less than or equal to 1:2. The invention uses the cheap, accessible and recyclable manganese acetate to replace noble metal, thereby reducing the cost; and the 1,3-disubstituted allylene ketone and thiophenol can smoothly react to produce the indenone-2-diphenyl sulfide derivatives. In addition, the substrates for 1,3-disubstituted allylene ketone and thiophenol have wide sources.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for preparing indanone, in particular to a method for synthesizing indanone-2-phenylene sulfide 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] The general formula of indanone-2-phenylene sulfide derivatives is as follows: [0004] There is a report in the literature: 1,1-diphenyl-3-phenylthioacrylic acid, under the action of phosphorus pentoxide or phosphorus pentachloride and se...

Claims

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Application Information

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IPC IPC(8): C07C323/22C07C319/18
Inventor 邹建平周军
Owner SUZHOU UNIV
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