5-acrylic oxo-trimethylene carbonate and its preparation and use

A technology of methyl carbonate and allyloxy, applied in the direction of organic chemistry, can solve the problems of high hydrophobicity, slow degradation performance, tissue cytocompatibility, etc.

Inactive Publication Date: 2005-10-12
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the main problems of biodegradable polycarbonate are the slow degradation performance caused by high hydrophobicity and the compatibility with tissue cells.

Method used

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  • 5-acrylic oxo-trimethylene carbonate and its preparation and use
  • 5-acrylic oxo-trimethylene carbonate and its preparation and use
  • 5-acrylic oxo-trimethylene carbonate and its preparation and use

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Preparation of 5-allyloxy-1,3-benzylidene glycerol: 18.0 g of 5-hydroxy-1,3-benzylidene glycerol and 100 ml of anhydrous tetrahydrofuran were placed in a 250 ml round bottom flask, and 6.0 g of hydrogenated Sodium, stirred for 8 hours, added 18 ml of allyl bromide, stirred for 24 hours. After filtration, the solvent was evaporated and dried to obtain 20.3 g of 5-allyloxy-1,3-benzylidene glycerol as a white solid, with a yield of 92%. The melting point is 50°C. Infrared spectrum 1645cm -1 (-CH 2 CHCH 2 ).

Embodiment 2

[0029] Preparation of 2-allyloxy-1,3-propanediol: 23.0 g of 5-allyloxy-1,3-benzylidene glycerol, 50 ml of methanol and 50 ml of 1M aqueous hydrochloric acid were placed in a 250 ml round bottom flask , reflux reaction for 24 hours. Pour into saturated potassium carbonate solution, extract with ethyl acetate, and distill off the solvent to obtain 12.8 g of colorless liquid 2-allyloxy-1,3-propanediol with a yield of 93%. Proton NMR spectrum ( 1 H NMR) (CDCl 3 , ppm): 5.90 (m, 1H, -CH 2 CH=CH 2 ), 5.30 (m, 2H, -CH 2 CH=CH 2 , 4.10 (d, 2H, O=COCH 2 CH-), 3.60(d, 2H, -OCH 2 CHCH 2 ), 3.46 (s, 1H, O=COCH 2 CH).

Embodiment 3

[0031] Preparation of 5-allyloxy-trimethylene carbonate: 13 g of 2-allyloxy-1,3-propanediol, 38 g of antipyrine and 200 ml of anhydrous THF were placed in a 500 ml round bottom flask In 10 ml of a solution of 7 g of triphosgene in tetrahydrofuran was added, and the reaction was carried out at 20° C. for 24 hours. After filtration, the solvent was distilled off to obtain 7.8 g of colorless liquid 5-allyloxy-trimethylene carbonate, with a yield of 50%. Proton NMR spectrum ( 1 H NMR) (CDCl 3 , ppm): 5.90 (m, 1H, -CH 2 CH=CH 2 ), 5.30 (m, 2H, -CH 2 CH=CH 2 ), 4.48 (s, 2H, O=COCH 2 CH-), 4.12(d, 2H, -OCH 2 CHCH 2 ), 3.90 (s, 1H, O-COCH 2 CH). Carbon-13 NMR spectrum ( 13 C NMR) (CDCl 3 , ppm): 147 (C=O), 133 (-OCH 2 CH=CH 2 ), 17 (-OCH 2 CH=CH 2 ), 77 (O=COCH 2 CH-), 70(-OCH 2 CHCH 2 ), 66 (O=COCH 2 CH). Infrared spectrum 1754cm -1 (C=O).

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Abstract

5-allyloxy-trimethylene carbonic ether, its production and use are disclosed. It is carried out by taking glycerine as material, selective protecting, closed cyclic reacting, and obtaining 5-allyloxy-trimethylene carbonic ether. The six-membered ring cyclic carbonic ether monomer containing functional group is used to synthesize multi-functional biological degradable/absorptive polyoctamethylene with good biological compatibility. It realizes medicine molecular carrier by bond key and ionogenic key style. It can be used for medicine controlling release, tissue engineering, artificial organ and gene treating.

Description

technical field [0001] The invention relates to 5-allyloxy-trimethylene carbonate, a preparation method and application thereof, and belongs to the field of organic synthesis. Background technique [0002] With the further in-depth and rapid development of the research and application of biomedical materials, biomedical materials and devices have increasingly become a high-tech pillar industry of the national economy. Among them, biodegradable polymers can be gradually degraded into small molecular products through hydrolysis or enzymolysis in the body, and finally excreted through normal physiological metabolic processes. The research hotspot and focus in the field of polymers have been widely used in the fields of human organ or tissue repair and replacement, controlled release of drugs, and gene delivery and transfection. At present, the main research and application of biomedical polymer materials include: polyester, polycarbonate, polyphosphate, polyester peptide, poly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06C08G64/02
Inventor 贺枫刘钢冯俊卓仁禧
Owner WUHAN UNIV
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