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Terphenyl compound and preparation method therefor and application thereof

A technology of ketone compounds and compounds, which is applied in the field of terphenyl compounds and their preparation and application, can solve the problems of precious metal catalysts and use prices, and achieve the effects of single product structure, convenient operation, and good practical value

Active Publication Date: 2015-12-23
邳州市润宏实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, such compounds are mainly prepared by coupling reactions such as Ullmann, Suzuki, Stille, Kumada, etc., but this method has disadvantages such as using expensive metal catalysts.

Method used

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  • Terphenyl compound and preparation method therefor and application thereof
  • Terphenyl compound and preparation method therefor and application thereof
  • Terphenyl compound and preparation method therefor and application thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0044] Preparation of compound (I-3)

[0045]Add 0.5635g (2.34mmol) 3,4-dimethoxy-6-bromophenylacetylene, 0.4670g (3.11mmol) p-methoxyacetophenone, 0.3570g (3.18mmol) t-BuOK to the test tube reactor , 5 ml DMSO. Heated in an oil bath at 100°C for 1.5h. After the reaction, add water, extract with dichloromethane, combine the organic layers, and concentrate the residue to separate by column chromatography (eluent is petroleum ether: ethyl acetate = 10: 1), 0.2844g of the target compound was obtained, with a yield of 31%. M.p.133-134℃

[0046] Preparation of compound (I-4)

[0047] Add 0.2101g (2.06mmol) phenylacetylene, 0.3123g (2.08mmol) p-methoxyacetophenone, 0.2467g (2.20mmol) t-BuOK, 5mlDMSO into the test tube reactor. Heated in an oil bath at 100°C for 1.5h. After the reaction, add water, extract with dichloromethane, combine the organic layers, and concentrate the residue to separate by column chromatography (eluent is petroleum ether: ethyl acetate = 10: 1), 0.3272g ...

Embodiment 1

[0080] Embodiment 1: the preparation of compound (II-1)

[0081] Add β, γ-unsaturated ketone (I-1) (0.1840g, 0.7293mmol) and cesium carbonate (0.2796g, 0.7967mmol) into the reaction vessel, mix in 1,4-dioxane (2mL), Stir and react in an oil bath at 90°C for 13 hours; after the reaction, add water, extract with dichloromethane, combine the organic layers, and concentrate the residue to separate by column chromatography (eluent is petroleum ether: dichloromethane: = 1: 1, V:V), collect R f The eluate with a value of 0.3-0.35 was distilled under reduced pressure and dried to obtain the target compound (II-1), 0.0821 g, with a yield of 61.8%.

[0082] 1 HNMR (500MHz, CDCl 3 )δ7.79(dd, J=8.0,1.9Hz,1H),7.73-7.72(m,3H),7.62(d,J=8.8Hz,2H),7.56(d,J=8.0Hz,1H), 7.43(t, J=7.4Hz1H), 7.33-7.29(m, 4H), 7.23(t, J=7.4Hz, 2H), 7.19-7.16(m, 1H), 7.02(d, J=8.8Hz, 2H ),3.88(s,3H)

[0083]

Embodiment 2

[0085] The cesium carbonate was changed to potassium tert-butoxide (0.0831g, 0.7405mmol), and other operations were the same as in Example 1 to obtain the target compound (II-1), 0.0774g, with a yield of 58.7%.

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Abstract

The invention discloses a terphenyl compound represented by a formula (II) and discloses a preparation method for the terphenyl compound and an application of the terphenyl compound in preparing anti-tumor drugs. The preparation method for the terphenyl compound disclosed by the invention is simple in process, mild in reaction condition, convenient to operate and low in cost and has a wide industrial application prospect. The product is single in structure, generates no isomers and has anti-tumor activity. The formula (II) is as shown in the description.

Description

(1) Technical field [0001] The invention relates to a new class of terphenyl compound, its preparation and anti-tumor application. (2) Background technology [0002] Compounds containing terphenyl structures often have good biological activities in terms of immunosuppressive activity, antioxidant activity, neuroprotective activity, cytotoxic activity, and antithrombotic and anticoagulant activities. In addition, this kind of compound also performs well in terms of liquid crystallinity and electroluminescence, and is widely used in liquid crystal materials. At present, such compounds are mainly prepared by coupling reactions such as Ullmann, Suzuki, Stille, Kumada, etc., but this method has disadvantages such as using expensive metal catalysts. Therefore, it is of great theoretical significance and practical application value to develop new synthetic methods to prepare terphenyl compounds with novel structures. (3) Contents of the invention [0003] The present invention ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/72A61P35/00
CPCC07C45/69C07C45/72C07C49/84C07C49/813C07C49/796
Inventor 崔冬梅俞婷婷石巍张辰
Owner 邳州市润宏实业有限公司
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