Diarylo[d,f]oxa-cycloheptane-3-ketone compound and synthesis method thereof

A technology for oxetane and ketone compounds, which is applied in the field of oxepane-3-one compounds and their synthesis, can solve the problems of inability to realize industrialized production, serious pollution, difficult compounds and the like, and achieves easy control , The effect of reducing environmental pollution and simple post-processing

Inactive Publication Date: 2012-10-17
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The purpose of the present invention is to solve the existing difficulties in synthesizing diaryl[d,f]oxepane-3-one compounds, serious

Method used

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  • Diarylo[d,f]oxa-cycloheptane-3-ketone compound and synthesis method thereof
  • Diarylo[d,f]oxa-cycloheptane-3-ketone compound and synthesis method thereof
  • Diarylo[d,f]oxa-cycloheptane-3-ketone compound and synthesis method thereof

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specific Embodiment approach 1

[0025] Specific embodiment 1: This embodiment is a diarylo[d,f]oxepane-3-one compound, and its chemical name is diphenyl[d,f]oxepane-3 - Ketone compound, structural formula is:

[0026]

[0027] The R 1 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 2 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 3 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 4 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 5 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -OH, -OBn or -ph; the R 6 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -OH, -OBn or -ph;...

specific Embodiment approach 2

[0028] Specific embodiment 2: This embodiment is a synthesis method of diarylo[d,f]oxepane-3-one compounds, whose chemical name is diphenyl[d,f]oxepane The synthetic method of alkane-3-one compound is completed according to the following steps: firstly, 2-phenylphenoxyacetic acid derivative is dissolved in an organic solvent, then trifluoroacetic anhydride / Lewis acid is added, and at a temperature of 0°C~ Stir the reaction at 80°C and a stirring speed of 300 rpm to 1500 rpm for 1h to 20h to obtain a reaction solution, pour the reaction solution directly into ice water, remove the water layer, and dissolve the organic layer I with sodium carbonate aqueous solution. The pH value of layer I was adjusted to 8 ~ 9, and the water layer was removed again. The obtained organic layer II was washed once with saturated brine, and then concentrated to recover the solvent to obtain a solid crude product. The solid crude product was recrystallized to obtain white powdery solid II. Benzo[d,f...

specific Embodiment approach 3

[0030] Specific embodiment three: the difference between this embodiment and specific embodiment two is: the structural formula of the 2-phenylphenoxyacetic acid derivative is:

[0031]

[0032] The R 1 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 2 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 3 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 4 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -F, -Cl, -Br, -OH, -OBn, -ph, -OCOCH 3 , -NO 2 , -NH 2 , -NHCOCH 3 , -CHO, -CHOCH 3 or The R 5 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -OH, -OBn or -ph; the R 6 For: -H, -OCH 3 、-CH 3 、-CH 2 CH 3 , n-Bu-, n-Pr-, -OH, -OBn or -ph; ...

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Abstract

The invention discloses a diarylo[d,f]oxacycloheptane-3-ketone compound and a synthesis method thereof, relating to an oxacycloheptane-3-ketone compound and a synthesis method thereof. The invention aims to solve the problems that in the prior art, the diarylo[d,f]oxacycloheptane-3-ketone compound is difficult to synthesize, the pollution is serious and the industrial production can not be realized. The structural formula of the diarylo[d,f]oxacycloheptane-3-ketone compound is shown in the specification. The method takes 2-phenylphenoxyacetic acid derivatives or 2-naphthphenoxyacetic acid derivatives as raw materials, and comprises the following steps of: carrying out reaction between trifluoroacetic anhydride and lewis acid as catalysts in an organic solvent; pouring ice water and layering; adjusting the pH value of the organic layer to 8-9 by the aqueous solution of sodium carbonate; washing the organic layer without a water layer by saturated salt water; and concentrating to obtain a solid crude product, and recrystallizing to obtain the diarylo[d,f]oxacycloheptane-3-ketone compound. The method disclosed by the invention is mainly used for synthesizing the diarylo[d,f]oxacycloheptane-3-ketone compound.

Description

technical field [0001] The present invention relates to oxepane-3-one compound and its synthesis method. Background technique [0002] Novel dibenzoxepane or azepane derivatives exhibit many pharmacokinetic activities, and it is found that it can inhibit the central nervous system through rat experiments. [0003] In 1968, Stephen (J.Med.Chem, 11(4), 895-896, 1968) found that the structure is The dibenzo[b,e][1,4]oxazepan-7-one has strong anti-inflammatory activity. [0004] In 1976, Katsujiro Ueno (J.Med.Chem, 21(7), 633-639, 1978) found that the non-planar structural formula is The 6,11-dihydro-11-oxodibenzo[b,e]oxepan-4-one has good anti-inflammatory activity. [0005] In 1984, Lawrence L. Martin (J.Med.Chem, 27(3), 372-376, 1984) found that the structural formula is 2-(4-oxo-4,10-dihydrobenzo[b]thieno[3,2-e]oxepan-6-yl)acetic acid and commonly used anti-inflammatory analgesic drug indomethacin It has a strong anti-inflammatory and analgesic effect. [0006] Dibe...

Claims

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Application Information

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IPC IPC(8): C07D313/10C07D313/06
Inventor 初文毅孙志忠宋树林袁小斌张婉莹于微微石晓红
Owner HEILONGJIANG UNIV
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