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Amide derivative containing double-bond gramine and preparation method and application thereof

A technology of amides and derivatives, which is applied in the field of amide derivatives containing double bonds and their preparations, can solve the problems of fast release rate, poor compounding performance, and reduced antifouling effect, so as to prevent adhesion , less environmental hazards, simple synthesis method

Inactive Publication Date: 2015-04-15
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these antifouling agents can only be used in antifouling coatings in the form of additives. In addition, the compounding performance of other components is poor, resulting in too fast release rate and greatly reducing the antifouling effect. Therefore, it stops at the application performance research in antifouling coatings

Method used

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  • Amide derivative containing double-bond gramine and preparation method and application thereof
  • Amide derivative containing double-bond gramine and preparation method and application thereof
  • Amide derivative containing double-bond gramine and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Preparation of N-allyl-3-(3-((dimethylamino)methyl)-1-indolyl)propionamide

[0048] 1. Preparation of N,N'-diallyldithiodipropionamide

[0049] Add 17.1g (0.3mol) allylamine and 2.5ml triethylamine in sequence to a 250mL three-necked flask equipped with a stirring device, a condenser, and a thermometer, and control the reaction temperature to 0°C through an ice-water bath. 23.8g (0.1mol) dimethyl β-dithiodipropionate was added dropwise within 2.5h. After the dropwise addition was completed, the ice-water bath was removed, and the reaction was continued at room temperature for 48 h. The reaction was terminated, and a yellow solid product was obtained by suction filtration. After being washed twice with water, dried, and recrystallized with ethanol, 25.5 g of white flaky crystals were obtained with a yield of 88.4% and a melting point of 135.7-137.2°C.

[0050] 2. Preparation of N-allyl-3-(1-indolyl)propionamide

[0051] Weigh 5.8g (0.05mol) of indole and 15...

Embodiment 2

[0057] Example 2: Preparation of N-allyl-3-(3-((dimethylamino)methyl)-5-bromo-1-indolyl)propionamide

[0058] 1. Preparation of N,N'-diallyldithiodipropionamide

[0059] The preparation method is the same as in Example 1.

[0060] 2. Preparation of N-allyl-3-(5-bromo-1-indolyl)propionamide

[0061] Weigh 9.8g (0.05mol) of 5-bromoindole and 15.1g (0.05mol) of N,N’-diallyldithiodipropionamide respectively and dissolve them in 50mL of anhydrous THF. Add 50mL of anhydrous THF and 3.6g (0.09mol) NaH (60% content) in sequence into a 250mL three-necked flask equipped with a stirring device and a thermometer, and add the THF solution of indole to the above system dropwise at 0°C. After dropping, continue to react for 30 minutes, then add the THF solution of N,N'-diallyldithiodipropionamide dropwise to the above system at 0°C. After dropping, the reaction was continued for 5 hours at room temperature. After the reaction, add 50mL of saturated NH 4 Cl solution, let it stand, take t...

Embodiment 3

[0066] Example 3: Preparation of N-allyl-3-(3-((dimethylamino)methyl)-5,6-dichloro-1-indolyl)propionamide

[0067] 1. Preparation of N,N'-diallyldithiodipropionamide

[0068] The preparation method is the same as in Example 1.

[0069] 2. Preparation of N-allyl-3-(5,6-dichloro-1-indolyl)propionamide

[0070] Weigh 9.3g (0.05mol) of 5,6-dichloroindole and 15.1g (0.05mol) of N,N’-diallyldithiodipropionamide respectively and dissolve them in 50mL of anhydrous THF. Add 50mL of anhydrous THF and 3.6g (0.09mol) NaH (60% content) in sequence into a 250mL three-necked flask equipped with a stirring device and a thermometer, and add the THF solution of indole to the above system dropwise at 0°C. After dropping, continue to react for 30 minutes, then add the THF solution of N,N'-diallyldithiodipropionamide dropwise to the above system at 0°C. After dropping, the reaction was continued for 5 hours at room temperature. After the reaction, add 50mL of saturated NH 4 Cl solution, let i...

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PUM

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Abstract

The invention relates to a compound having a structure formula (I) shown in the specification, wherein in the formula, X1 is H, Cl or Br, and X2 is H or Cl. The invention also relates to a preparation method of the compound in the formula (I), and zinc acrylate / copper resin obtained by taking the compound as a comonomer, and further relates to use of the resin as a marine antifouling material. The zinc acrylate / copper resin obtained by taking the amide derivative having the structure shown in the general formula (I) and containing double-bond gramine as the comonomer has good self-polishing property in sea water, and a gramine-derived structure with an antifouling function can be slowly released, so that adhesion of marine fouling organisms is effectively prevented.

Description

【Technical field】 [0001] The invention relates to a derivative of anophylline, in particular to an amide derivative containing a double bond of anophylline, and a preparation method and application thereof. 【Background technique】 [0002] At present, anti-fouling paint is the most economical, effective and commonly used method in the attachment and growth technology of anti-fouling organisms. Antifouling agents in antifouling coatings, such as organotin and DDT (DDT), are the key components that determine their antifouling performance, but because they cause huge pollution to the marine environment, there is an urgent need to develop environmentally friendly antifouling agents . [0003] Natural product antifouling agents extracted from secondary metabolites of marine organisms have attracted much attention due to their high antifouling activity and low environmental hazards. Among them, the antifouling activity of the indole alkaloid 2,5,6-tribromo-1-methyltropine extract...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14C08F220/60C08F220/06C09D5/16C09D133/24
CPCC07D209/14C08F226/02C08F2800/20C09D5/1637C08F220/14C08F220/1804C08F220/06
Inventor 李霞倪春花闫雪峰赵海洲姜晓辉于良民李昌诚董磊夏树伟张志明孙明亮
Owner OCEAN UNIV OF CHINA
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