A kind of indole compound, its synthetic method and its antifouling use

A synthesis method and technology of indoles, applied in the fields of botanical equipment and methods, antifouling/underwater coatings, applications, etc., can solve problems such as no detailed reports on antifouling activity, and achieve simple structure and mild reaction conditions. , the effect of high antifouling activity

Active Publication Date: 2021-10-15
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Indole antifouling agents are the most promising antifouling agents so far. The research on indole compounds as antifouling agents has made great progress. However, the current research on indole antifouling agents mainly focuses on There are indole-3-carboxaldehydes of substituents on the 3-position and the compounds of catarrhines, but there are no detailed reports on the antifouling activity of indole compounds of other structures. Therefore, it is necessary to develop an economical, The method for efficiently synthesizing indole compounds will bring significant economic and social benefits to the development of this field

Method used

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  • A kind of indole compound, its synthetic method and its antifouling use
  • A kind of indole compound, its synthetic method and its antifouling use
  • A kind of indole compound, its synthetic method and its antifouling use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] Step (1), first prepared an adjacent fluorophenyl chloride: Take 146 mg (1.2 mmol) of oxfluorobenzoic acid in a dry 25 ml round bottom flask, add 10 ml of anhydrous anhydrous methylenechloromethane, then add The chloride sulfoxide was 0.13 ml (1.8 mmol), heated refluxed for 2 h, evaporated to evaporate dichloromethane and excess of dichloroalkylene sulfoxide under reduced pressure.

[0023] Step (2), weigh 200 mg of substrate a, placed in a 25 ml dry round bottom flask, and mixed 10 ml of anhydrous methylene chloroform and dissolve, 0.90 mmol of 0.90 mmol), stirred for 20 minutes. In the ice water bath placed at 0 ° C, the methyl chloride solution of the benzoyl chloride was slowly added dropwise, and the reaction liquid was stirred at room temperature for 2 h, TLC (PE: EA = 4: 1) detection The substrate reaction is complete. Add an appropriate amount of saturated NaHCO to the reaction liquid 3 The reaction was quenched. The organic phase was extracted 3 times wi...

Embodiment 2

[0031]

[0032] White oil, 1 H-NMR (400MHz, CDCL 3 ), δ7.98-6.99 (m, 6H), 6.88-6.39 (m, 2H), 5.66-4.01 (M, 1H), 3.66-3.17 (m, 1H), 3.10 (DT, J = 12.9, 6.1Hz, 1H), 2.64 (S, 3H), 2.56-0.84 (M, 2H), 1.56-0.84 (M, 2H) .13C NMR (100 MHz, CDCL3) δ171.52 ( C), 164.58 (C), 148.86 (C), 137.70 (CH), 125.85 (CH), 123.58 (CH), 122.10 (CH), 120.40 (CH), 119.43 ( CH), 117.06 (CH), 115.01 (CH), 108.24 (CH), 86.74 (C), 43.19 (CH2), 38.25 (CH3), 34.19 (CH2), 18.29 (CH2).

[0033] MS (ESI (+)) Calcd for C 19 Hide 19 FN 2 O 2 [M + h] + : 326.4; Found: 327.0.

Embodiment 3

[0035]

[0036] Colorless oil, 1 H-NMR (400MHz, CDCL 3), δ7.74-7.37 (m, 2H), 7.25-6.95 (m, 4H), 6.88-6.32 (M, 2H), 5.28 (S, 1H), 4.43-4.00 (m, 1H), 3.64-3.16 (M, 1H), 3.14 -2.79 (m, 3H), 2.60 (m, 2H), 2.09-1.22 (m, 1H), 1.57-1.22 (m, 1H). 13C NMR (100MHz, CDCL3) Δ172.16 (C), 163.35 (C), 148.92 (C), 133.43 (C), 132.32 (C), 131.63 (CH), 130.24 (CH), 130.15 (CH), 129.64 (CH), 129.39 (CH), 122.15 (CH), 119.32 (CH), 115.65 (CH), 108.13 (CH), 86.84 (C), 43.31 (CH2), 38.35 (CH3), 34.16 (CH2), 18.24 (CH2).

[0037] MS (ESI (+)) Calcd for C 19 Hide 19 FN 2 O 2 [M + h] + : 326.4; Found: 327.0.

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Abstract

The present invention relates to indole compound, its synthesis method and its antifouling application. The structural formula of the compound is: the preparation method is to firstly prepare the reaction reagent to obtain the acid chloride product. Weigh the anhydrous dichloromethane solution of substrate a, add triethylamine dropwise, add dropwise the dichloromethane solution of the acid chloride product under the condition of ice-water bath, wait until the dropwise addition is complete, move the reaction solution to room temperature and stir, After detection, the reaction of the substrate is complete, the reaction is quenched, the organic phase is extracted with dichloromethane, the organic phases are combined, concentrated under reduced pressure, and the crude product is separated by column chromatography to obtain indole compounds. The synthesis process is simple, the product is of high purity, has high bactericidal activity against Staphylococcus aureus, Ralstonia solanacus and Bacillus cereus, and has excellent application prospects.

Description

Technical field [0001] The present invention relates to an indole compound and its antifouling activity, in particular a use of air pollution such as ships, terminal equipment, marine drilling platform pillars. Background technique [0002] Ocean dirt is also known as ocean adhesion organisms, usually refers to marine organisms that grow on parts and marine artificial facilities in ship shell waterlines, including marine animals, plants and microorganisms. . There are three major categories: (1) accelerate metal corrosion; (2) Reduce marine facility; (3) affect the production and quality of the aquaculture industry. Take the ship as an example, the adhesion of marine organisms in the bottom of the boat increases the fuel consumption of ships by 40%, and the sailing cost is as high as 77%. It will take about $ 3 billion in the world. In addition, marine biofilms are also very serious to corrosion damage to marine terminal equipment, sea water cooling pipe, power plant cooling towe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01N43/90A01P1/00C09D5/16
CPCA01N43/90C07D471/04C09D5/1625
Inventor 郑绍军朱瑞魏洋韩珂唐冰蔡星伟陈立庄
Owner JIANGSU UNIV OF SCI & TECH
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