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Method for synthesizing tetrahydronaphthalene-2-alcohol derivative compound

A technology of alcohol derivatives and compounds, which is applied in the field of compound preparation, can solve the problems of difficult acquisition of reaction raw materials, low yield of key intermediates, and harsh reaction conditions, and achieve the effects of high selectivity, simple route, and mild reaction conditions

Active Publication Date: 2020-07-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at overcoming the problems of difficult acquisition of reaction raw materials, low yield of key intermediates, harsh reaction conditions, cumbersome steps, etc. Naphthalene-2-ol derivative-like approach to direct intramolecular C(sp 3 )-H arylation, synthesis of tetrahydronaphthalene-2-ol derivatives, simple route, high yield, good universality, mild reaction conditions, high selectivity, in terms of atom economy and environmental friendliness It is said that it is an ideal synthesis method

Method used

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  • Method for synthesizing tetrahydronaphthalene-2-alcohol derivative compound
  • Method for synthesizing tetrahydronaphthalene-2-alcohol derivative compound
  • Method for synthesizing tetrahydronaphthalene-2-alcohol derivative compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] A method for synthesizing tetralin-2-alcohol derivatives, comprising the steps of:

[0067] (1) Add compound I (133.8mg, 0.3mmol), palladium acetate (3.4mg, 0.015mmol), N-fluorobisbenzenesulfonamide (0.142g, 0.45mmol), 1,2- Dichloroethane (3mL), closed stirring reaction at 90°C for 24h, R in compound I 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 Both are hydrogen;

[0068] (2) Dilute the mixed solution obtained in step (1) with ethyl acetate (10mL), filter and remove the solvent under reduced pressure, and the residue is subjected to column chromatography [GF254 silica gel; 100-200 mesh; developer is V (petroleum ether) / V (ethyl acetate)=50 / 1] separation and purification, collecting the eluent containing the product, and distilling off the solvent from the eluent to obtain 115.9 mg of intermediate product II (yield 87%);

[0069] The obtained intermediate product II is carried out structural analysis, and the results are as follows:

[0070] White solid; 1 H...

Embodiment 2

[0076] A method for synthesizing tetralin-2-alcohol derivatives, comprising the steps of:

[0077] (1) Add compound I (144.6mg, 0.3mmol), palladium chloride (5.4mg, 0.03mmol), N-fluorobisbenzenesulfonamide (0.142g, 0.45mmol), 1,2 -dichloroethane (3mL), closed stirring reaction at 90°C for 24h, R in compound I 1 , R 2 , R 5 , R 6 are hydrogen, R 3 , R 4 Connect to form a benzene ring, and form a naphthyl group together with the original benzene ring;

[0078] (2) Dilute the mixed solution obtained in step (1) with ethyl acetate (10mL), filter and remove the solvent under reduced pressure, and the residue is subjected to column chromatography [GF254 silica gel; 100-200 mesh; developer is V (petroleum ether) / V (ethyl acetate)=50 / 1] separation and purification, collecting the eluent containing the product, and distilling off the solvent from the eluent to obtain 112.3 mg of intermediate product II (yield 78%);

[0079] The obtained intermediate product II is carried out st...

Embodiment 3

[0087] A method for synthesizing tetralin-2-alcohol derivatives, comprising the steps of:

[0088] (1) Add compound I (156.6mg, 0.3mmol), palladium acetate (6.8mg, 0.03mmol), selectfluor (0.159g, 0.45mmol), 1,2-dichloroethane (3mL) in a closed reaction vessel , Stir the reaction at 90°C for 24h, the R in compound I 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are hydrogen, R 8 is phenyl;

[0089] (2) Dilute the mixed solution obtained in step (1) with ethyl acetate (10mL), filter and remove the solvent under reduced pressure, and the residue is subjected to column chromatography [GF254 silica gel; 100-200 mesh; developer is V (petroleum ether) / V (ethyl acetate)=50 / 1] separation and purification, collecting the eluate containing the product, and distilling off the solvent from the eluent to obtain 120.1 mg of intermediate product II (yield 77%);

[0090] The obtained intermediate product II is carried out structural analysis, and the results are as follows:

[0091] White s...

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Abstract

The invention relates to the technical field of compound preparation, and discloses a method for synthesizing a tetrahydronaphthalene-2-alcohol derivative compound, which comprises the following steps: (1) mixing a compound I with a palladium catalyst, an oxidant and a solvent, and carrying out sealed stirring reaction at 70-130 DEG C for 1-24 hours; carrying out post-treatment on the mixed solution obtained in the step (1) to obtain an intermediate product II; mixing the intermediate product II with a catalyst, acetonitrile and water, replacing air with nitrogen, and carrying out closed stirring reaction at 85-95 DEG C for 1-24 hours; and carrying out post-treatment on the mixed solution obtained in the step (3) to obtain a final product III, namely, the tetrahydronaphthalene-2-alcohol derivative compound. According to the method, intramolecular C (sp3)-H arylation is directly carried out through cross dehydrogenation coupling between inert C (sp3)-H and C (sp2)-H bonds to synthesizea benzopyran-3-alcohol derivative compound, the route is simple, the yield is high, the universality is good, the reaction condition is mild, and the selectivity is high.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a method for synthesizing tetralin-2-ol derivative compounds. Background technique [0002] Tetralin-2-ol derivatives are important skeleton structures for biological activity in various compounds. Compounds of this type are widely found in natural products and have high biological activity. They are valuable in petrochemical and manufacturing industries. Materials are important intermediates in the pharmaceutical industry, and are widely used in the synthesis of drugs for the treatment of skin, eye diseases, precancerous symptoms and other diseases. For example: Corynoline and DeN-Corynoline, which are antiarrhythmic, antibacterial, and hepatoprotective, contain tetralin-2-ol derivatives. [0003] Although there are synthetic reports of tetralin derivatives in the prior art, for example, a "method for producing tetrahydronaphthalene derivatives" disclosed in Chines...

Claims

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Application Information

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IPC IPC(8): C07C29/09C07C35/36C07C35/37C07C35/52C07C41/26C07C43/23
CPCC07C29/09C07C41/26C07C249/12C07C35/36C07C35/37C07C35/52C07C43/23C07C251/38
Inventor 郝宏艳娄绍杰毛羊杰许丹倩徐振元
Owner ZHEJIANG UNIV OF TECH
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