Fullerene single catechol derivative intermediate, preparation method thereof and purposes thereof

A technology of fullerene monocatechol and intermediates, which is applied in the field of preparation of polymer materials, can solve the problem of short-term detoxification function, and achieve the effect of broadening performance and function

Inactive Publication Date: 2015-04-22
INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its detoxification function is short-term, and it must be injected within 3 hours after uranium poisoning to be effective.

Method used

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  • Fullerene single catechol derivative intermediate, preparation method thereof and purposes thereof
  • Fullerene single catechol derivative intermediate, preparation method thereof and purposes thereof
  • Fullerene single catechol derivative intermediate, preparation method thereof and purposes thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 1) Preparation of N-Boc-ethylenediamine

[0049] Add 4.5 parts of ethylenediamine and 40 parts of dichloromethane into a reaction flask equipped with a stirrer, and vigorously stir at room temperature. Slowly add Boc to the reaction flask through a constant pressure dropping funnel 2 O12 parts, 40 parts of dichloromethane solution, the whole dropwise addition process continued for 8 to 10 hours, continued to stir for 18 to 22 hours, then removed the solvent under reduced pressure, concentrated to 100 to 110 parts, poured 10 parts of sodium carbonate solution (aq. 20%), separated, the aqueous phase was extracted three times with dichloromethane, each time with 10 parts of dichloromethane, combined with the organic phase, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain a colorless 9.14 parts of mono-Boc-protected ethylenediamine product, yield 98%, without further purification, the product was directly used i...

Embodiment 2

[0063] Compounds (1) to (4) were prepared according to the preparation methods 1) to 4) in Example 1;

[0064] 5) Preparation of Intermediate IV

[0065] Suspend 0.02 parts of Intermediate III in 0.6 parts of dichloromethane, add 0.04 parts of trifluoroacetic acid, stir at room temperature, and monitor the progress of the reaction by TLC (developer: petroleum ether: ethyl acetate = 2:1). The reaction time is 10 h, and the reaction After the end, add 2mol·L -1 NaOH solution to neutralize to a pH value of 13.5, filter with suction, and wash the filter cake three times with water. Obtained 0.15 parts of solid, yield 85.3%;

[0066] 6) Preparation of target objects

[0067] Add 0.6 parts of 3,4-dihydroxybenzoic acid into a reaction flask with a stirrer, then add 1 part of dimethylformamide (DMF) to dissolve, and slowly add 2.7 parts of K to the solution under stirring. 2 CO 3 , then add 3.5 parts of benzyl bromide dropwise under stirring at room temperature, stir overnight af...

Embodiment 3

[0072] Compounds (1) to (4) were prepared according to the preparation methods 1) to 4) in Example 1;

[0073] 5) Preparation of Intermediate IV

[0074] Suspend 0.02 parts of intermediate III in 0.8 parts of dichloromethane, add 0.06 parts of trifluoroacetic acid, stir at room temperature, and monitor the reaction progress by TLC (developing solvent: petroleum ether: ethyl acetate = 2:1), the reaction time is 10.5h, After the reaction, add 2mol L -1 The NaOH solution was neutralized to a pH value of 14, suction filtered, and the filter cake was washed three times with water to obtain 0.1 part of solid, yield: 87%;

[0075] 6) Preparation of target objects

[0076] Add 6 parts of 3,4-dihydroxybenzoic acid into a reaction flask with a stirrer, then add 8 parts of DMF to dissolve, and slowly add 28 parts of K to the solution under stirring. 2 CO 3 , then add 35 parts of benzyl bromide dropwise under stirring at room temperature, stir overnight after the dropwise addition is ...

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Abstract

The invention discloses a fullerene single catechol derivative intermediate, a preparation method thereof and purposes thereof. The preparation method is characterized in that 0.3-14 parts of 3,4-dibenzyloxybenzoic acid are dissolved in 2-10 parts of tetrahydrofuran at -15--18 DEG C, 0.01-1 part of triethylamine is added in the solution, 0.09-1 part of ethyl chloroformate is dripped in the reactor, the solution is stirred for 2-3 hours, triethylamine hydrochloride is removed through filtering, THF is removed in a pressure reducing mode, 0.1-4.0 parts of fullerene ethylenediamine derivatives intermediates IV, and 16-100 parts of methylbenzene are added in the solution and react at 140-150 DEG C, TLC is used for detecting reaction progresses, the methylbenzene is removed after filtration and pressure reduction, 1-10 parts of dichloromethane are added and dissolved in the solution, 6-7 parts of saturated salt water is used for washing for three times, 10-12 parts of saturated sodium bicarbonate are sued for washing for five times, anhydrous sodium sulfate is used for washing organic phases, the column chromatography developing solvent includes dichloromethane and ethyl acetate with a ratio of 20:1, and 0.05-2.5 parts of fullerene single catechol derivatives intermediates V are obtained. The productive rate is 30.6%-38.8%.

Description

technical field [0001] The invention relates to a fullerene monocatechol derivative intermediate, a preparation method and application thereof, and belongs to the field of preparation of polymer materials. Background technique [0002] In order to effectively respond to and control nuclear and radiation emergencies in a timely manner, prevent the spread of the situation, reduce the consequences of accidents, protect the lives and health of the masses, maintain social stability and economic development, it is necessary to do a good job in nuclear and radiation emergencies. protective work. [0003] Nuclear radiation hazards are not only manifested in direct exposure to the outside and body surface, but more serious hazards are manifested in internal exposure to personnel caused by radioactive substances entering the body through the respiratory tract, digestive tract or skin [Liu Changan, Chen Erdong, Liu Ying. Classification of casualties in incidents[J]. Chinese Journal of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/56A61P39/04
CPCC07D209/96
Inventor 何佳恒刘国平蹇源魏洪源陈静罗军益陈琪萍马宗平钟文彬
Owner INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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