A kind of amphiphilic molecule containing o-nitrobenzyl ester photodegradation group and its synthesis method

A technology of o-nitrobenzyl ester and amphiphilic molecules, which is applied in the field of synthesis of new light-controlled surface active molecules, can solve the problems of low yield and achieve the effects of high yield, mild reaction conditions and high activity

Inactive Publication Date: 2020-06-02
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Li Quan and others cleverly used DBU to catalyze the carboxylic acid reaction of o-nitrobenzyl bromide and diethylenetriaminepentaacetic acid dianhydride with different carbon chain lengths to synthesize a series of o-nitrobenzyl esters, but the yield was low, only 18.2%. ~18.6%

Method used

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  • A kind of amphiphilic molecule containing o-nitrobenzyl ester photodegradation group and its synthesis method
  • A kind of amphiphilic molecule containing o-nitrobenzyl ester photodegradation group and its synthesis method
  • A kind of amphiphilic molecule containing o-nitrobenzyl ester photodegradation group and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Synthesis of diethylenetriaminepentaacetic acid dianhydride (DTPAA)

[0040] Add 2g of DTPA, 2.5mL of anhydrous acetic anhydride, and 3.5mL of anhydrous pyridine into a 50mL single-necked flask. Under the protection of nitrogen, heat and reflux at 65°C. After 24 hours of reaction, a dark brown suspension is obtained. Filter the filter cake with anhydrous Wash with acetic anhydride and anhydrous ether alternately until colorless, and dry in vacuum at 80°C for 12 hours to obtain 1.51 g of white solid with a melting range of 178°C to 181°C and a yield of 83.2%.

[0041] (2) Demethylene reaction:

[0042]Dissolve 1g of 6-nitropiperonal in 10mL of organic solvent, add dropwise into 2.5g of aluminum chloride organic solvent, and react for 2h under ice-cooling. After the reaction was completed, the reaction solution was poured into 25 mL of hydrobromic acid, and stirred at room temperature for 48 h. The reaction mixture was diluted with a large amount of water, extracted...

Embodiment 2

[0050] (1) Synthesis of diethylenetriaminepentaacetic acid dianhydride (DTPAA)

[0051] With embodiment 1.

[0052] (2) Demethylene reaction

[0053] With embodiment 1.

[0054] (3) etherification reaction:

[0055] Add the alkali solution and 3.97g of dodecane bromide into the organic solution of 1g of 4,5-dihydroxy-2-nitrobenzaldehyde, and react at 60°C for 15h under the protection of nitrogen. The reaction mixture was diluted with a large amount of water, extracted three times with ether, dried over anhydrous magnesium sulfate, and the filtrate obtained by suction filtration was spin-dried, recrystallized in a solvent and filtered by suction to obtain a yellow solid 4,5-didodecyloxy-2-nitro Benzaldehyde 2.12g, the yield is 79.4%.

[0056] Such as figure 1 As shown, the 4,5-didodecyloxy-2-nitrobenzaldehyde 1 H NMR diagram, 1 H-NMR (500MHz, CDCl 3 ): δin ppm0.86-0.90(t,6H,-CH 2 -CH 3 ); 1.26-1.49(m,36H,-(CH 2 ) 9 -CH 3 ); 1.85-1.90 (m,4H,-O-CH 2 -CH 2 -); 4.10-...

Embodiment 3

[0066] (1) Synthesis of diethylenetriaminepentaacetic acid dianhydride (DTPAA)

[0067] With embodiment 1.

[0068] (2) Demethylene reaction

[0069] With embodiment 1.

[0070] (3) etherification reaction:

[0071] Add the alkali solution and 5.45 g of bromooctadecane to the organic solution of 1 g of 4,5-dihydroxy-2-nitrobenzaldehyde, and react at 60° C. for 15 h under the protection of nitrogen. The reaction mixture was diluted with a large amount of water, extracted three times with ether, dried over anhydrous magnesium sulfate, and the obtained filtrate was spin-dried, recrystallized in a solvent and filtered to obtain a yellow solid 4,5-dioctadecyloxy-2-nitro Benzaldehyde 2.82g, the yield is 74.9%.

[0072] (4) Reduction reaction:

[0073] Add 0.55g of sodium borohydride to 2g of 4,5-dioctadecyloxy-2-nitrobenzaldehyde in a mixed solution of methanol and tetrahydrofuran, react at -7~0°C for 30min, and react at room temperature for 3h. After the reaction was complete...

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Abstract

The present invention relates to the field of surfactants. Disclosed are a novel photodegradable amphiphilic molecule and synthesis method therefor. The synthesis of the photodegradable amphiphilic molecule has five steps of reactions: (1) performing dehydration with diethylenetriaminepentaacetic acid as a raw material and acetic anhydride as a dehydrant under pyridine catalysis to generate diethylenetriaminepentaacetic dianhydride; (2) performing methylene removal on 6-nitropiperonal under the action of aluminum chloride and hydrobromic acid; (3) etherificating 4,5-dihydroxy-2-nitrobenzaldehyde with bromoalkane under an alkaline condition; (4) reducing 4,5-dihydroxy-2-nitrobenzaldehyde to 4,5-dihydroxy-2-nitrobenzyl alcohol under the action of a reductant; and (5) esterificating the 4,5-dihydroxy-2-nitrobenzyl alcohol with an excess amount of diethylenetriaminepentaacetic dianhydride to obtain an o-nitrobenzyl ester-based amphiphilic molecule. According to the present invention, the reaction condition of an o-nitrobenzyl alcohol and diethylenetriaminepentaacetic dianhydride is mild, and the use of an excess amount of diethylenetriaminepentaacetic dianhydride reduces the occurrence of a side reaction. The amphiphilic molecule has good ultraviolet degradation performance.

Description

technical field [0001] The invention relates to a method for synthesizing a novel light-controlled surface active molecule, in particular to using o-nitrobenzyl ester as a photodegradation group, double-long carbon chains as a hydrophobic group, and diethylenetriaminepentaacetic acid as a hydrophilic group A new surface active molecule and a new synthesis method thereof belong to the field of surfactants. Background technique [0002] Photocontrollable drug carriers are an emerging class in liposomes. After it is excited by light, the chemical bonds in the molecule are broken, and the drug molecules protected by the carrier are effectively released to complete the controlled release of the drug. Due to its non-invasive drug delivery, controllable release at a specific time and a given space, and its excellent characteristics of transporting nucleic acid, protein and other biologically active molecules, it has become a viable carrier for biological drugs and has received a l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/16C07C227/18A61K9/127A61K47/18
CPCA61K9/127A61K47/183C07C229/16
Inventor 乔卫红姚维贺王宁
Owner DALIAN UNIV OF TECH
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