Delta-valerolactone compounds, preparation method and application

A compound, valerolactone technology, applied in δ-valerolactone compounds and its preparation method and application field, can solve the problems of accumulation, polyethylene glycol cannot be degraded, aliphatic polyester does not have hydrophilicity, etc. , to achieve the effect of a wide range of sources

Active Publication Date: 2015-02-11
YINGU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the human body does not have the ability to degrade polyethylene glycol, polyethylene glycol with a higher degree of polymerization cannot be excreted through the kidneys and will accumulate in the human body
[0004] In order to overcome the problems that polyethylene glycol cannot be degraded and aliphatic polyesters do not have hydrophilicity, and simultaneously have the biocompatibility and hydrophilicity of polyethylene glycol, and the biodegradability of polyester, the present invention Provide a δ-valerolactone compound and polyester prepared therefrom

Method used

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  • Delta-valerolactone compounds, preparation method and application
  • Delta-valerolactone compounds, preparation method and application
  • Delta-valerolactone compounds, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The synthesis line:

[0046]

[0047] (1) Under ice-salt bath conditions, add 3.45g sodium metal, 14.6g (0.1mol) diethyl oxalate, 10.00g (0.1mol) compound 1δ-valerolactone to 100mL ethanol, and react in ice bath for 1 hour, React at room temperature for 10 hours, remove the solvent, add water to the residue, wash the aqueous phase with ether, acidify the aqueous phase with hydrochloric acid, extract with dichloromethane, dry and remove the solvent to obtain compound 3 as a yellow liquid;

[0048] (2) Add 0.1 mol NaH with a purity of 60% to 150 mL of anhydrous tetrahydrofuran and stir to form a suspension, then add compound 3 obtained in step 1) dropwise, and react until there are no bubbles to obtain compound 5;

[0049] (3) Continue to feed formaldehyde gas into the above reaction solution, filter after 30 minutes, remove the solvent from the filtrate, and purify to obtain yellow liquid compound 7;

[0050] (4) Dissolve compound 7 obtained in step 3) in dichlorom...

Embodiment 2

[0054]

[0055] (1) Under ice-salt bath conditions, add 3.45g sodium metal, 14.6g (0.1mol) diethyl oxalate, 10.00g (0.1mol) compound 1δ-valerolactone to 100mL ethanol, and react in ice bath for 1 hour, React at room temperature for 10 hours, remove the solvent, add water to the residue, wash the aqueous phase with ether, acidify the aqueous phase with hydrochloric acid, extract with dichloromethane, dry and remove the solvent to obtain compound 2 as a yellow liquid;

[0056] (2) Add 0.1 mol NaH with a purity of 60% to 150 mL of anhydrous tetrahydrofuran and stir to form a suspension, then add compound 3 obtained in step 1) dropwise, and react until there are no bubbles to obtain compound 5;

[0057] (3) Continue to feed formaldehyde gas into the above reaction solution, filter after 30 minutes, remove the solvent from the filtrate, and purify to obtain yellow liquid compound 7;

[0058] (4) Dissolve compound 7 obtained in step 3) in dichloromethane, add 6.8 g of compound 4 ...

Embodiment 3

[0062] The synthetic route of is as follows:

[0063]

[0064] Under anhydrous, oxygen-free, and argon protection conditions, add 0.0011g (0.00001mol) of compound 11 benzyl alcohol to 0.292g (0.001mol) of compound 10, stir well and add 0.0069g of catalyst 1,5,7-triaza Bicyclo[4.4.0]dec-5-ene (TBD), stirred for 1 day, added 20mL of dichloromethane and 0.1g of benzoic acid, and evaporated to remove the solvent; the product was dissolved in 10mL of methanol and placed in a 1000Da dialysis bag. Dialyzed with methanol for 2 days to obtain 0.42 mmol of light yellow oily liquid polyester with a yield of 42%.

[0065] The physical parameters of the yellowish oily liquid polyester: M n =6557, M w = 7444, PDI = 1.13.

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Abstract

The invention discloses delta-valerolactone compounds having structures expressed by a general formula (I); the invention further discloses a preparation method of the compounds, polyester prepared from the compounds and a preparation method thereof; the raw materials of the delta-valerolactone compounds prepared by the invention are extensive and renewable; and the polyester prepared from the delta-valerolactone compounds has biocompatibility and degradable hydrophily and can be utilized in a plurality of purposes, for example, medicine conveyance, protein protection, and the like.

Description

technical field [0001] The invention relates to a delta-valerolactone compound, a preparation method and an application thereof, and belongs to the field of macromolecules. Background technique [0002] Biodegradable aliphatic polyesters, thermoplastics are a very valuable class of biomedical materials. Their application in the biomedical field has promoted the development of new materials. In order to reduce metal residues and improve the physical, chemical, and biological properties of polyesters, the development and utilization of biodegradable functionalized polyesters has attracted increasing attention. However, aliphatic polyesters are generally not hydrophilic and cannot be effectively transported between tissues in the human body. [0003] Polyethylene glycol is a representative of hydrophilic polymers, because it can be dissolved in both water and most organic solvents, and has the characteristics of good biocompatibility, non-toxicity, and low immunogenicity. . ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/30C08G63/688C08G63/87
CPCC08G63/6882A61K47/34
Inventor 李敏峰龚兵何兰李化杨懿赵永晔
Owner YINGU PHARMA
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