Delta-valerolactone compounds, preparation method and application

A compound, the technology of valerolactone, 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: 2013-09-11
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

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

Example Embodiment

[0044] Example 1

[0045] The synthetic line:

[0046]

[0047] (1) Add 3.45g sodium metal, 14.6g (0.1mol) diethyl oxalate, and 10.00g (0.1mol) compound 1δ-valerolactone to 100mL ethanol under ice-salt bath conditions, and react for 1 hour in ice bath. 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, and dry to remove the solvent to obtain compound 3 as a yellow liquid;

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

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

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

Example Embodiment

[0053] Example 2

[0054]

[0055] (1) Add 3.45g sodium metal, 14.6g (0.1mol) diethyl oxalate, and 10.00g (0.1mol) compound 1δ-valerolactone to 100mL ethanol under ice-salt bath conditions, and react for 1 hour in ice bath. 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, and dry to remove the solvent to obtain compound 2 as a yellow liquid;

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

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

[0058] (4) Dissolve compound 7 obtained in step 3) in dichloromethane, a...

Example Embodiment

[0061] Example 3

[0062] The synthetic route is as follows:

[0063]

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

[0065] Physical parameters of the slightly yellow oily liquid polyester: M n =6557, M w =7444, PDI=1.13.

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PUM

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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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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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