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A kind of functional siloxane containing phenazine and its synthesis method

A synthesis method and siloxane technology, applied in chemical instruments and methods, dyeing organosilicon compound treatment, compounds of group 4/14 elements of the periodic table, etc., can solve the problem of rare varieties and single special function of functional siloxane and other issues to achieve the effect of high conversion rate

Inactive Publication Date: 2016-07-13
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the shortcoming of single special function and rare species of functional siloxane, the purpose of the present invention is to provide a novel multifunctional siloxane containing phenazine and its synthesis method

Method used

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  • A kind of functional siloxane containing phenazine and its synthesis method
  • A kind of functional siloxane containing phenazine and its synthesis method
  • A kind of functional siloxane containing phenazine and its synthesis method

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Experimental program
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Embodiment 1

[0038] The functional siloxane compound containing phenazine is synthesized according to the following method, and the synthetic route is as follows:

[0039]

[0040] Concrete synthetic steps are as follows:

[0041] (1) Synthesis of 5,10-dihydrophenazine

[0042] N 2 Under protection, in a 250ml three-necked flask equipped with electromagnetic stirring and temperature control devices, dissolve phenazine (0.56g, 3.108mmol) in 20ml of boiling ethanol, and dissolve 80ml of sodium dithionite (2.24g, 10.92mmol) within 1h Add the aqueous solution dropwise to the above-mentioned ethanol solution of phenazine. After the dropwise addition, stir and react at room temperature for 2.5~5h. After the reaction is completed, filter the reaction mixture, rinse the filter cake with water, and dry to obtain 5,10-dihydrophene Oxyzine 0.54g; Yield 95%.

[0043] (2) Synthesis of 5,10-dihydrophenazine-5-carbamoyl chloride

[0044] N 2 Under protection, in a 250ml three-neck flask equipped ...

Embodiment 2

[0050] Synthesis of Functional Siloxane Compound A Containing Phenazine

[0051] N 2 Under protection, in a 250ml three-necked flask equipped with electromagnetic stirring and temperature control devices, 15ml of ether solution of 3-aminopropyltrimethoxysilane (0.72g, 4mmol) was added dropwise to the 5,10 - Dihydrophenazine-5-carbamoyl chloride (0.586g, 2.4mmol) and triethylamine (0.606g, 6mmol) in 150ml ether solution, TLC detection reaction, react at room temperature for 6~8h, the reaction is over Finally, the white precipitate was filtered off, the filtrate was distilled off under reduced pressure to remove diethyl ether, and the crude product was separated and purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain 0.70 g of light yellow functional siloxane compound A liquid containing phenazine . Yield: 75%.

[0052] Structural identification of phenazine-containing functional siloxane compound A: 1 H-NMR (400MHz, CDCl 3 )δ7.37(d,J=7.9Hz,2H...

Embodiment 3

[0054] Synthesis of 5,10-dihydrophenazine-5-carbamoyl chloride

[0055] N 2 Under protection, in a 250ml three-necked flask equipped with electromagnetic stirring and temperature control device, di-tert-butyl dicarbonate (1.605g, 7.5mmol) (or phosgene 0.7425g, 7.5mmol; or diphosgene 1.478g, 7.5mmol ; or dimethyl carbonate (0.676g, 7.5mmol) in 20ml of dichloromethane was added dropwise to 5,10-dihydrophenazine (0.451g, 2.5mmol) and triethylamine (1.515g, 15mmol) in 100ml of dichloromethane In methane solution, thin layer tracking detection reaction, reaction at room temperature for 8~10h, after the reaction, dichloromethane was distilled off under reduced pressure, and the crude product was separated and purified by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain micro Yellow solid intermediate 0.43g, after 1 H-NMR test showed that it was intermediate 5,10-dihydrophenazine-5-carbamoyl chloride, and the yield was 70%.

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Abstract

The invention discloses a functional siloxane containing phenazine and a synthetic method thereof. The synthetic method comprises the following steps: (1) synthetizing 5,10-dihydrophenazine by taking phenazine and sodium hydrosulfite as raw materials; (2) synthetizing 5,10-dihydrophenazine-5-carbamyl chloride by taking 5,10-dihydrophenazine and triphosgene as raw materials; (3) reacting the carbamyl chloride compound with 3-aminopropyltriethoxysilane to obtain a functional siloxane compound containing phenazine, which is proved to be the functional siloxane containing phenazine by infrared spectroscopy and <1>H-NMR determination. The compound structurally contains a plurality of functional groups, namely siloxane, amide, carbamido, phenazine and the like, and has potential application value in the aspects such as drug sustained release, a molecular imprinting identification material, a rare-earth luminescent material, white carbon black modification and the like. According to the synthetic method disclosed by the invention, the production efficiency is high, the synthetic path is short and the preparation technology is simple.

Description

technical field [0001] The invention belongs to the field of preparation of functional organosilicon compounds, in particular to a functional siloxane containing phenazine and a synthesis method thereof. Background technique [0002] Functional organosiloxane is an important class of organosilicon compounds. It is a class of compounds developed for some special purposes. Its molecules have reactive groups that can chemically bond with inorganic substances and chemically bond with organic substances. The reactive group, its structural formula can be expressed as (OR) 3 Si(CH 2 ) n Y, n=0~3: R is an alkyl group, usually methyl, ethyl, etc.; Y is an organic functional group, usually vinyl, amino, epoxy, mercapto or ureido, etc. Functional organosiloxanes are mainly used in surface treatment of inorganic materials, modification of polymer materials and surface protection of metal materials. Commonly used functional organosiloxanes are KH-550, KH-560, KH-570, KH- 590 and othe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C09C1/56C09C3/12C08G77/26B01J20/26B01J20/30
Inventor 童跃进李翔高勇关怀民戴宏邹行郭静
Owner FUJIAN NORMAL UNIV