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6,7-dihydro-5H-diphenyl[a,c]cyclohepta-5-ketone compound and preparation method thereof

A technology of ketone compounds and compounds, applied in the field of organic synthesis

Inactive Publication Date: 2014-12-24
LUOYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To the best of our knowledge, a multimetal-catalyzed ortho-bromoarylmethanol and arylethanone (or o-bromoarylethylketone and arylmethanol) can be synthesized via α-alkylation and carbon-hydrogen bond activation in one step6,7 -Dihydro-5H-diphenyl[a,c]cycloheptan-5-ones have not been reported yet

Method used

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  • 6,7-dihydro-5H-diphenyl[a,c]cyclohepta-5-ketone compound and preparation method thereof
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  • 6,7-dihydro-5H-diphenyl[a,c]cyclohepta-5-ketone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 6,7-dihydro-5H-diphenyl[a,c]cycloheptan-5-one (1)

[0018] Under the protection of inert gas (such as high-purity nitrogen), add 1.0mmol benzyl alcohol, 2.0mmol o-bromoacetophenone, 0.01mmol [ Ir(cod)Cl] 2 , 0.1 mmol of palladium acetate, 1.0 mmol of silver carbonate, 0.1 mmol of 1,1'-binaphthyl-2,2'-bis-diphenylphosphine, 1.0 mmol of cesium hydroxide and 5 ml of dioxane, and replace the reaction tube with nitrogen three times , and then heated to 110°C with an oil bath under magnetic stirring, and the reaction was refluxed for 24 hours. The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrated with a rotary evaporator, and the concentrated solid is recrystallized with dichloromethane as a solvent t...

Embodiment 2

[0020] Example 2: Preparation of 9-methyl-6,7-dihydro-5H-diphenyl[a,c]cycloheptan-5-one (2)

[0021] Under the protection of inert gas (such as high-purity nitrogen), add 2.0mmol 2-bromo-5-methylbenzyl alcohol and 1.0mmol benzene to a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous and oxygen-free operation). Ethanone, 0.05mmol [Ir(cod)Cl] 2 , 0.1mmol palladium chloride, 3.0mmol silver acetate, 0.12mmol 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, 2.0mmol potassium hydroxide and 5ml toluene, replace the reaction tube with nitrogen for 3 times, and then Heated to 110° C. with an oil bath under magnetic stirring, and the reaction was refluxed for 6 hours. The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes and filter; the filtrate is concentrat...

Embodiment 3

[0023] Example 3: Preparation of 10-methoxy-6,7-dihydro-5H-diphenyl[a,c]cycloheptan-5-one (5)

[0024] Under the protection of an inert gas (such as high-purity nitrogen), add 1.0 mmol p-methoxybenzyl alcohol and 1.6 mmol o-bromoacetophenone to a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous and oxygen-free operation) , 0.08mmol [Ir(cod)Cl] 2 , 0.2mmol palladium trifluoroacetate, 3.0mmol silver trifluoroacetate, 0.2mmol 1,1'-binaphthyl-2,2'-bisdiphenylphosphine, 3mmol potassium carbonate and 5ml benzene, replace the reaction tube with nitrogen three times, Then it was heated to 60° C. with an oil bath under magnetic stirring, and the reaction was refluxed for 48 hours. The oil bath was removed, and the water bath was lowered to room temperature; 3ml of water was added to the reaction solution, extracted three times with 5ml of dichloromethane, the organic phases were combined and washed with anhydrous MgSO 4 Dry for 30 minutes and filter; the fi...

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Abstract

The invention relates to a 6,7-dihydro-5H-diphenyl[a,c]cyclohepta-5-ketone compound and a preparation method thereof. A formula of the compound is as shown in the specification. O-bromoaryl methanol, aryl ethanone, [Ir(cod)Cl]2, a palladium salt, a sliver salt, 1,1'-binaphthyl-2,2'-bisdiphenylphosphine and alkaline are taken and added into an organic solvent, heated and refluxed in the presence of an N2 gas, filtered, evaporated and re-crystallized after the reaction is ended to obtain the 6,7-dihydro-5H-diphenyl[a,c]cyclohepta-5-ketone compound. The 6,7-dihydro-5H-diphenyl[a,c]cyclohepta-5-ketone compound is synthesized by one step, wherein the reaction substrate scope is wide, the yield is high, the reaction is economical and efficient, and the application prospect is wide.

Description

[0001] technical field [0002] The invention relates to the technical field of organic synthesis, in particular to 6,7-dihydro-5H-diphenyl[a,c]cycloheptan-5-one compounds and a preparation method thereof. Background technique [0003] Allocolchicine ( ) compounds are important anticancer drugs, which have the advantages of unique mechanism of action, high-efficiency activity and significant curative effect on solid tumors, and have attracted people's attention. The development of such drugs has broad market prospects. Allolcolchicine is isolated from the flowers of the lily plant colchicine, and its product variety and output are limited, which cannot meet the market demand. Now the synthesis method of allocolchicine derivatives has been greatly developed, and the most important intermediate in its synthesis is 6,7-dihydro-5H-diphen[a,c]cycloheptan-5-one compound ( ). The synthesis of this intermediate has been reported in the literature, but the reaction steps are ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/675C07C49/755C07C49/697C07C255/56C07C49/757C07C69/76C07C69/738C07C45/68C07C253/30C07C67/343
CPCC07C45/68C07C67/343C07C253/30C07C2603/32C07C49/675C07C49/697C07C49/757C07C49/755C07C69/76C07C255/56
Inventor 娄新华李红梅王志强付维军徐晨
Owner LUOYANG NORMAL UNIV
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