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Preparation method of allyl phenol compound

A technology for allyl phenol and compound, which is applied in the field of preparation of allyl phenol compounds, can solve the problems of high reaction temperature, low selectivity, low yield and the like, and achieves the effects of reducing reaction temperature and improving yield

Pending Publication Date: 2022-04-26
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the technical problems of high reaction temperature, low selectivity and low yield in the synthesis of allyl phenol compounds existing in the prior art, and to provide a preparation method of allyl phenol compounds method

Method used

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  • Preparation method of allyl phenol compound
  • Preparation method of allyl phenol compound
  • Preparation method of allyl phenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] This example provides a method for preparing 4-allyl-3-fluorophenol. In an argon atmosphere, add 4-diazo-3-fluorocyclohexyl-2,5-diene sequentially into a 10mL Schlenk tube -1-ketone (0.3mmol), Molecular sieves (60mg), then add anhydrous dichloromethane DCM (1.0mL), and stir for 1 minute, then add allylboronic acid pinacol ester (0.9mmol, 3.0 equivalents),

[0024] Rh 2 (esp) 2 (2mol%, 4.55mg) and dichloromethane (1.0mL). Then the above reaction mixture was stirred at room temperature until the complete consumption of the quinone diazide was monitored by TLC analysis. After the reaction was completed, the TLC plate detected that a product was generated.

[0025] Its reaction equation is as follows:

[0026]

[0027] After the reaction, the reaction mixture was filtered and washed with dichloromethane (20 mL), spin-dried, and the residue was separated through a silica gel column to obtain a pale yellow oily product with a yield of 94%. The NMR data of the product ...

Embodiment 2

[0029] This example provides a method for preparing 4-allyl-3-chlorophenol. In an argon atmosphere, add 4-diazo-3-chlorocyclohexyl-2,5-diene sequentially into a 10 mL Schlenk tube -1-ketone (0.3mmol), then add anhydrous dichloromethane DCM (2.0mL), and stir for 1 minute, then add allylboronic acid pinacol ester (0.9mmol, 3.0 equivalents), Rh 2 (esp) 2 (2mol%, 4.55mg) and dichloromethane (1.0mL). Then the above reaction mixture was stirred at room temperature and normal pressure until the quinone diazide was completely consumed by TLC analysis. After the reaction was completed, the TLC plate detected that a product was generated.

[0030] Its reaction equation is as follows:

[0031]

[0032] After the reaction, the reaction mixture was filtered and washed with dichloromethane (20 mL), spin-dried, and the residue was separated through a silica gel column to obtain a pale yellow oily product with a yield of 93%. The NMR data of the product are as follows: 1 H NMR (300MHz, ...

Embodiment 3

[0034] This example provides a method for preparing 4-allyl-3-bromophenol. In an argon atmosphere, 4-diazo-3-bromocyclohexyl-2,5-diene is sequentially added to a 10 mL Schlenk tube -1-ketone (0.3mmol), Molecular sieves (75mg), then add anhydrous dichloromethane DCM (1.0mL), and stir for 1 minute, then add allylboronic acid pinacol ester (0.9mmol, 3.0 equivalents), Rh 2 (esp) 2 (2mol%, 4.55mg) and dichloromethane (0.5mL). Then the above reaction mixture was stirred at room temperature and normal pressure until the quinone diazide was completely consumed by TLC analysis. After the reaction was completed, the TLC plate detected that a product was generated.

[0035] Its reaction equation is as follows:

[0036]

[0037]After the reaction was finished, the reaction mixture was filtered and washed with dichloromethane (20 mL), spin-dried, and the residue was separated through a silica gel column to obtain a pale yellow oily product with a yield of 85%. The NMR data of the pr...

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Abstract

The invention discloses a preparation method of an allyl phenol compound, which comprises the following steps: reacting a mixed reaction system containing a diazoquinone compound, allyl borate, a catalyst and a solvent at room temperature in a protective atmosphere, and separating to obtain the allyl phenol compound. Under the catalysis of the catalyst Rh2 (esp) 2, the allylphenol compound can be rapidly and efficiently synthesized from the diazoquinone compound and the allylboronic acid ester only under the conditions of room temperature and normal pressure, the reaction yield can reach 85% or above, and the highest yield reaches 94%; in addition, only the allyl phenol compound with a single structure is generated in the reaction; therefore, the reaction temperature for synthesizing the allylphenol compound is obviously reduced, and the reaction can be efficiently performed only at room temperature (23 + / -2 DEG C); meanwhile, the yield of the allyl phenol compound and the regioselectivity of the reaction are obviously improved.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of allylphenol compounds. Background technique [0002] Allylphenol is an important structural motif present in numerous natural compounds with a range of biological and pharmacological activities. For example, Honokiol and γ-Mangostin were found to have various biological activities, including anticancer and antiviral properties. Cathafurans exhibit antibacterial, antioxidant, anti-inflammatory and cytotoxic activities. It has been reported that Pestalone exhibits high-efficiency antibiotic activity against Staphylococcus aureus and is cytotoxic to various tumor cells. Petalostemumol G5 and Obtustyrene show antibacterial properties PestalachlorideA is an antifungal compound. [0003] The Claisen rearrangement of allyl phenyl ethers and the Friedel-Craft allylation of phenols are two commonly used methods for the synthesis of allyl phenols. Although these...

Claims

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Application Information

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IPC IPC(8): C07C37/20C07C41/26C07C67/343C07C39/373C07C69/84C07C43/23C07C39/19C07B41/02
CPCC07C37/20C07C67/343C07C41/26C07B41/02C07C39/373C07C69/84C07C43/23C07C39/19
Inventor 周聪颖饶俊鑫
Owner JINAN UNIVERSITY
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