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Method for synthesis of benzfluorenone and its derivative by copper as catalyst

A technology of benzofluorenone and a synthesis method, which is applied in the field of organic compound synthesis, can solve the problems of difficult preparation of reaction raw materials, numerous reaction steps, long reaction time, etc., and achieves low-cost and easy-to-obtain catalysts and strong substrate universality. , the effect of easy operation

Active Publication Date: 2015-11-25
常熟市知识产权运营中心有限公司
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Problems solved by technology

[0005] In order to solve the problems such as difficult preparation of reaction raw materials, high reaction temperature, numerous reaction steps, low yield and long reaction time in the current synthetic method of benzofluorenone and its derivatives, the present invention proposes a method using copper as The synthesis method of the catalyst benzofluorenone and its derivatives, the present invention replaces expensive noble metals with base metals, replaces multi-component raw materials with simple and easy-to-obtain 1,6-enynes, and realizes the reaction under milder conditions

Method used

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  • Method for synthesis of benzfluorenone and its derivative by copper as catalyst
  • Method for synthesis of benzfluorenone and its derivative by copper as catalyst
  • Method for synthesis of benzfluorenone and its derivative by copper as catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Add 0.2mmol of 3-phenyl-1-(2'-phenylethynyl)phenyl-2-allyl ketone, 0.4mmol of Selectfluor and 0.01mmol of Cu powder into a 15mL thick-walled pressure-resistant reaction tube, and then add 2mL of acetonitrile as a solvent. Then, it was magnetically stirred at room temperature for 3 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=15:1 as an eluent). The material was an orange solid, 76% yield.

[0023]

[0024] Characterization data: 1 HNMR (500MHz, CDCl 3 ): δ=8.26(s, 1H), 7.97(dd, J 1 =7.5Hz,J 2 = 1.5Hz, 1H), 7.76(dd, J 1 =6.5Hz,J 2 =0.9Hz, 1H), 7.65-7.60(m, 3H), 7.51-7.42(m, 5H), 7.26-7.19(m, 2H), 6.35(d, J=7.5Hz, 1H); 13 CNMR (125MHz, CDCl 3 ): δ=193.2, 145.2, 137.4, 136.9, 136.5, 135.3, 134.70, 134.66, 133.4, 132.6, 13...

Embodiment 2

[0026] Add 0.2mmol of 3-phenyl-1-(2'-phenylethynyl)phenyl-2-allyl ketone, 0.4mmol of DDQ and 0.01mmol of Cu powder into a 15mL thick-walled pressure-resistant reaction tube, and then add 2mL of 1,2-dichloro Ethane as solvent. Then, it was magnetically stirred at room temperature for 3 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=15:1 as an eluent). The material was an orange solid, 70% yield.

[0027]

[0028] Characterization data: 1 HNMR (500MHz, CDCl 3 ): δ=8.26(s, 1H), 7.97(dd, J 1 =7.5Hz,J 2 = 1.5Hz, 1H), 7.76(dd, J 1 =6.5Hz,J 2 =0.9Hz, 1H), 7.65-7.60(m, 3H), 7.51-7.42(m, 5H), 7.26-7.19(m, 2H), 6.35(d, J=7.5Hz, 1H); 13 CNMR (125MHz, CDCl 3 ): δ=193.2, 145.2, 137.4, 136.9, 136.5, 135.3, 134.70, 134.66, 133.4, 132.6, 130....

Embodiment 3

[0030]Add 0.2mmol of 3-phenyl-1-(2'-phenylethynyl)phenyl-2-allyl ketone, 0.4mmol of Oxone and 0.01mmol of Cu powder into a 15mL thick-walled pressure-resistant reaction tube, and then add 2mL of 1,4-diox Hexacyclic as a solvent. Then, it was magnetically stirred at room temperature for 3 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=15:1 as an eluent). The material was an orange solid, 68% yield.

[0031]

[0032] Characterization data: 1 HNMR (500MHz, CDCl 3 ): δ=8.26(s, 1H), 7.97(dd, J 1 =7.5Hz,J 2 = 1.5Hz, 1H), 7.76(dd, J 1 =6.5Hz,J 2 =0.9Hz, 1H), 7.65-7.60(m, 3H), 7.51-7.42(m, 5H), 7.26-7.19(m, 2H), 6.35(d, J=7.5Hz, 1H); 13 CNMR (125MHz, CDCl 3 ): δ=193.2, 145.2, 137.4, 136.9, 136.5, 135.3, 134.70, 134.66, 133.4, 132.6, 1...

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Abstract

The invention relates to an organic compound synthetic method and provides a method for synthesis of benzfluorenone and its derivative by copper as a catalyst. The method solves the problem that the existing benzfluorenone and its derivative synthesis method utilizes difficultly prepared reaction raw materials and has a high reaction temperature, a lot of reaction processes, a low yield and long reaction time. The method comprises that 1, 6-eneyne shown in the structural formula (I) as an initiator is dissolved in a solvent, the solution undergoes a reaction under the action of a copper catalyst and an oxidizing agent at a temperature of 0-60 DEG C for 1-12h, and the benzfluorenone shown in the structural formula (II) and its derivative are obtained by separation and purification. The method utilizes a base metal to replace an expensive precious metal, utilizes simple and easily available 1, 6-eneyne to replace a multicomponent raw material and realizes a reaction under mild conditions. The reaction formula is shown in the following description.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing benzofluorenone and its derivatives using copper as a catalyst. Background technique [0002] Fluorenone and its derivatives are important fine chemical intermediates, which are widely used in the fields of medicine, plastics, dyes and organic electroluminescent materials. As one of the fluorenone derivatives, benzofluorenone compounds also play an important role in the field of life sciences. For example, canafrenone (4,5,10-trihydroxy-9-methoxy-2-methyl-11H-benzofluoren-11-one) has antitumor and bactericidal effects; FluostatinsA (6,7-di Hydroxy-3-methyl-11H-benzofluorene-1,4,11-trione) is also biologically active. Bisphenol fluorene synthesized from fluorenone can be used to modify resin and polyester, which can improve its transparency, refractive index and high temperature resistance. Therefore, the research and development of the re...

Claims

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Application Information

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IPC IPC(8): C07C49/665C07C49/697C07C45/61
Inventor 刘运奎张剑吴德贵
Owner 常熟市知识产权运营中心有限公司
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