N-amino alkyl substituted glucosamide as well as preparation method and application thereof

Abstract

The invention discloses N-amino alkyl substituted glucosamide as well as a preparation method and an application thereof. The N-amino alkyl substituted glucosamide is shown in formula (I), wherein n=2, 4, 6, 8 or 12. Supra-molecular gel formed by the N-amino alkyl substituted glucosamide in a solvent has thermal reversibility and thixotropy. Two-component gel formed by the N-amino alkyl substituted glucosamide in a solvent also has thermal reversibility and thixotropy. The instantaneous response rate after thixotropy is high, full response can be realized, and the thixotropy process is reversible and can be repeated. Gel with thixotropy is expected to be used in fields of coating, paint, pigment and the like.

Description

technical field

[0001] The invention belongs to the technical field of fine chemicals, and in particular relates to N-aminoalkyl substituted glucamides and a preparation method and application thereof. Background technique

[0002] Low-molecular-weight organic gelling factors self-assemble into a three-dimensional network structure in a solvent through hydrogen bonds, π-π stacking, van der Waals forces, and other non-covalent bonds to gel the solvent molecules. Due to the non-covalent bond interaction between molecules, the gel can realize the reversible transition between the sol state and the gel state under the stimulation of certain conditions. Therefore, it has potential application value in many fields such as smart materials, pharmaceutical science and life science.

[0003] As a smart material, thixotropic gel has attracted the attention of many researchers, but there are not many structures of thixotropic gel factors. YuFang et al. found that dimeric steroids form...

Examples

Embodiment 1

[0034] Raw material 2,4-(3,4-dichlorobenzylidene)-D-methyl gluconate (II) used in the present invention is made by following method:

[0035]

[0036] Add 215.8 g of 50 wt % D-gluconic acid aqueous solution (0.55 mol of D-gluconic acid), 100 mL of methanol, and 200 mL of concentrated hydrochloric acid into a 1L four-necked flask equipped with mechanical stirring and a thermometer at room temperature, and stir at 200 rpm. Add a methanol solution of 3,4-dichlorobenzaldehyde (dissolve 87.5g (0.50mol) of 3,4-dichlorobenzaldehyde in 300mL of methanol), and the system becomes viscous after 4 hours of reaction. Minute speed stirring reaction for 20h, after the reaction is completed, add 100mL water to the system, stir for 2h and then filter with suction, wash the filter cake with a large amount of water until the pH is 6-7, then wash twice with 200mL of hot dichloromethane, and drain to obtain Product II, dried to yield 140 g. The yield was 76%, and the melting point was 188.6-18...

Embodiment 2

[0038] The preparation method of N-aminoalkyl substituted glucamide comprises the steps:

[0039] With 4-dimethylaminopyridine (DMAP) as catalyst, 2,4-(3,4-dichlorobenzylidene)-D-gluconate methyl ester (II) and aliphatic diamine (NH 2 C n h 2n NH 2 ) is a raw material, and pyridine or methanol is a synthesized N-aminoalkyl-substituted glucose amide molecule (I) under the condition of a solvent, and the reaction equation is as follows.

[0040]

[0041] Said n=2, 4, 6, 8 or 12.

Embodiment 3

[0043] N-(2-aminoethyl)-2,4-(3,4-dichlorobenzylidene)-D-glucamide (G 2 ) preparation method:

[0044] Add 5.00g (0.014mol) 2,4-(3,4-dichlorobenzylidene)-D-gluconic acid methyl ester (II) to a 250mL four-neck flask equipped with a mechanical stirrer and a thermometer at 10°C , 50 mL of pyridine was used as the solvent, and 0.01 g (0.008 mmol) of DMAP was used as the catalyst. After stirring for 30 min, 2.52 g (0.042 mol) of 1,2-ethylenediamine was added and stirred overnight at room temperature. After the reaction was completed, 25 mL of water was added to the system, stirred for 2 hours, then filtered with suction, and the filter cake was washed with water, then washed with methanol and dried to obtain a crude product. The crude product was refluxed in 20 mL of methanol for 30 min, cooled to room temperature, stirred for 1 h and then filtered with suction. The filter cake was washed with methanol and dried to obtain 3.9 g. Compound N-(2-aminoethyl)-2,4-(3,4-dichlorobenzylide...

technical field

[0001] The invention belongs to the technical field of fine chemicals, and in particular relates to N-aminoalkyl substituted glucamides and a preparation method and application thereof. Background technique

[0002] Low-molecular-weight organic gelling factors self-assemble into a three-dimensional network structure in a solvent through hydrogen bonds, π-π stacking, van der Waals forces, and other non-covalent bonds to gel the solvent molecules. Due to the non-covalent bond interaction between molecules, the gel can realize the reversible transition between the sol state and the gel state under the stimulation of certain conditions. Therefore, it has potential application value in many fields such as smart materials, pharmaceutical science and life science.

[0003] As a smart material, thixotropic gel has attracted the attention of many researchers, but there are not many structures of thixotropic gel factors. YuFang et al. found that dimeric steroids form...

Examples

Embodiment 1

[0034] Raw material 2,4-(3,4-dichlorobenzylidene)-D-methyl gluconate (II) used in the present invention is made by following method:

[0035]

[0036] Add 215.8 g of 50 wt % D-gluconic acid aqueous solution (0.55 mol of D-gluconic acid), 100 mL of methanol, and 200 mL of concentrated hydrochloric acid into a 1L four-necked flask equipped with mechanical stirring and a thermometer at room temperature, and stir at 200 rpm. Add a methanol solution of 3,4-dichlorobenzaldehyde (dissolve 87.5g (0.50mol) of 3,4-dichlorobenzaldehyde in 300mL of methanol), and the system becomes viscous after 4 hours of reaction. Minute speed stirring reaction for 20h, after the reaction is completed, add 100mL water to the system, stir for 2h and then filter with suction, wash the filter cake with a large amount of water until the pH is 6-7, then wash twice with 200mL of hot dichloromethane, and drain to obtain Product II, dried to yield 140 g. The yield was 76%, and the melting point was 188.6-18...

Embodiment 2

[0038] The preparation method of N-aminoalkyl substituted glucamide comprises the steps:

[0039] With 4-dimethylaminopyridine (DMAP) as catalyst, 2,4-(3,4-dichlorobenzylidene)-D-gluconate methyl ester (II) and aliphatic diamine (NH 2 C n h 2n NH 2 ) is a raw material, and pyridine or methanol is a synthesized N-aminoalkyl-substituted glucose amide molecule (I) under the condition of a solvent, and the reaction equation is as follows.

[0040]

[0041] Said n=2, 4, 6, 8 or 12.

Embodiment 3

[0043] N-(2-aminoethyl)-2,4-(3,4-dichlorobenzylidene)-D-glucamide (G 2 ) preparation method:

[0044] Add 5.00g (0.014mol) 2,4-(3,4-dichlorobenzylidene)-D-gluconic acid methyl ester (II) to a 250mL four-neck flask equipped with a mechanical stirrer and a thermometer at 10°C , 50 mL of pyridine was used as the solvent, and 0.01 g (0.008 mmol) of DMAP was used as the catalyst. After stirring for 30 min, 2.52 g (0.042 mol) of 1,2-ethylenediamine was added and stirred overnight at room temperature. After the reaction was completed, 25 mL of water was added to the system, stirred for 2 hours, then filtered with suction, and the filter cake was washed with water, then washed with methanol and dried to obtain a crude product. The crude product was refluxed in 20 mL of methanol for 30 min, cooled to room temperature, stirred for 1 h and then filtered with suction. The filter cake was washed with methanol and dried to obtain 3.9 g. Compound N-(2-aminoethyl)-2,4-(3,4-dichlorobenzylide...

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