CN108997219A - A kind of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer and preparation method - Google Patents
A kind of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer and preparation method Download PDFInfo
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- CN108997219A CN108997219A CN201810724749.9A CN201810724749A CN108997219A CN 108997219 A CN108997219 A CN 108997219A CN 201810724749 A CN201810724749 A CN 201810724749A CN 108997219 A CN108997219 A CN 108997219A
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- vinyl imidazole
- ethoxy
- function monomer
- chloride ion
- ion liquid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
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Abstract
The present invention relates to a kind of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer and preparation method, ionic liquid cation is 1- (2- ethoxy) -3- vinyl imidazole cation, and anion is chloride ion.The ionic liquid is the more excellent function monomer of TP5, the multiple interactions such as hydrogen bond, electrostatic, π-be pi-conjugated can be formed with template molecule TP5 simultaneously, reduce destruction of the hydrone to active force between the two, the accuracy that function monomer acts on template molecule is substantially increased, it is highly beneficial to trace of the TP5 in water phase.Ionic liquid function monomer 1- (2- ethoxy) -3- vinyl imidazole chlorine ([HeVIM] Cl) provided by the invention and template molecule TP5 have very strong interaction, and imprinting efficiency is higher.It is shown with the fluorescence emission spectrum and uv-vis spectra of template molecule (TP5) pre-polymerization nanocrystal composition, produces multiple, stronger interaction between the two, imprinting efficiency is high, highly beneficial to trace of the template molecule in water phase.
Description
Technical field
The invention belongs to function of molecular engram material and its preparation technical fields, are related to a kind of 1- (2- ethoxy) -3- second
Alkenyl imidazoles chloride ion liquid function monomer and preparation method are a kind of 1- (2- hydroxyls for being used for thymopeptide-5 molecule (TP5) trace
Ethyl) -3- vinyl imidazole chloride ion liquid ([HeVIM] Cl) function monomer.
Background technique
Thymopoietin (TP) is the polypeptide for 49 amino acid of one kind isolated from people's thymic tissue, average molecular matter
The single polypeptide compound that amount is 5562, it, which has, promotes thymocyte and periphery T cell and B cell differentiation and development, adjusts machine
The bioactivity such as body immunity function.Thymopeptide-5 (TP5) is artificial synthesized pentapeptide, by arginine, lysine, asparagine
It is residue segment that five kinds of acid, valine, tyrosine amino acid compositions, which are the 32-36 of thymopoietin, still has thymopoietin
Activity.It can be clinically used for treatment malignant tumour, rheumatoid arthritis, hepatitis B and immunodeficiency syndrome
Deng.
Molecular imprinting technology is to identify that a certain substance carries out polymerization reaction and forms imprinted polymer by wanting selection
Method.The polymer prepared by this method has very high identification capability, can be accurately effective according to molecular structure
Ground selects correspondingly target molecule.Polymer based on technology preparation is in strong acid and strong base, high temperature and pressure and compared with adverse circumstances
In still keep higher selective recognition capability and high stability.Thymus gland five can be effectively and rapidly separated using molecular imprinting technology
Peptide.Currently, being suitable for the function monomer of trace thymopeptide-5 (TP5) in water phase mainly has acrylic acid (AA), methacrylic acid
(MAA), hydroxy-ethyl acrylate (HEMA) and acrylamide (AM) etc. realize trace by forming hydrogen bond action with thymopeptide-5.
Since intermolecular hydrogen bonding effect is highly susceptible to the interference and destruction of hydrone in aqueous environment, imprinting efficiency and accurate is reduced
Property, therefore substantially reduce the recognition effect of specificity.
Ionic liquid (Ionic liquids, ILs) refer to it is being in a liquid state at or near room temperature, by zwitterion structure
At organic fuse salt, have structured good design and good dissolubility, can pass through adjust zwitterion combination
Obtain variety classes, ionic liquid of different nature；ILs has good dissolubility to organic matter or inorganic matter, by dividing
Son designs the adjusting, it can be achieved that inorganic matter, water, organic matter and polymer solubility.According to good in ionic liquid structure
The features such as designability and stronger solvability, can be used as reaction dissolvent and function monomer is applied in molecular imprinting technology.
Currently, there is not yet regarding 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid ([HeVIM] Cl) as thymus gland five
The research of peptide molecule (TP5) trace function monomer is reported.
Summary of the invention
Technical problems to be solved
In order to avoid the shortcomings of the prior art, the present invention proposes a kind of 1- (2- ethoxy) -3- vinyl imidazole chlorine
Ionic liquid function monomer and preparation method, for common function monomer in current techniques to thymopeptide-5 molecule (TP5) trace
Ineffective problem.The ionic liquid and thymopeptide-5 molecule of this method preparation have multiple action power, can reduce water phase ring
Effective trace and identification of the thymopeptide-5 in aqueous phase system are realized in the influence that border acts on the two.
Technical solution
A kind of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer, it is characterised in that: ionic liquid
Molecular structure are as follows:
A kind of preparation side of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer described in claim 1
Method, it is characterised in that steps are as follows:
Step 1: ethylene chlorhydrin being mixed with 1- vinyl imidazole 1:1.2 molar ratio, in 80 DEG C, is passed through under nitrogen protection and stirs
Reaction 18~for 24 hours is mixed, faint yellow glutinous thick liquid is obtained；
Step 2: faint yellow glutinous thick liquid obtained by step 1 being washed 3~5 times with ether, to remove unreacted 1- second
Alkenyl imidazoles；
Step 3: product dry 10~12h in 50 DEG C of electric vacuum drying oven after washing obtained by step 2 is obtained
To 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid ([HeVIM] Cl) function monomer of pale yellow transparent.
The hybrid mode of the ethylene chlorhydrin and 1- vinyl imidazole are as follows: mixing liquid is entered three mouthfuls using dropwise addition mode
In flask.
The rate of addition of every part of mixing liquid is 30~40min completion.
The ethylene chlorhydrin is dried.
The 1- vinyl imidazole is distilled.
Beneficial effect
A kind of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer proposed by the present invention and preparation side
Method is a kind of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid for being used for thymopeptide-5 molecule (TP5) trace
([HeVIM] Cl) function monomer.Ionic liquid cation is 1- (2- ethoxy) -3- vinyl imidazole cation, and anion is
Chloride ion.
The method of the present invention simple process.The ionic liquid is the more excellent function monomer of TP5, can simultaneously and template molecule
TP5 forms the multiple interactions such as hydrogen bond, electrostatic, π-be pi-conjugated, reduces destruction of the hydrone to active force between the two, significantly
The accuracy that function monomer acts on template molecule is improved, it is highly beneficial to trace of the TP5 in water phase.It is provided by the invention
Ionic liquid function monomer 1- (2- ethoxy) -3- vinyl imidazole chlorine ([HeVIM] Cl) has very strong with template molecule TP5
Interaction, imprinting efficiency are higher.With the fluorescence emission spectrum and uv-vis spectra of template molecule (TP5) pre-polymerization nanocrystal composition
Display produces multiple, stronger interaction between the two, and imprinting efficiency is high, to trace ten of the template molecule in water phase
Divide advantageous.
Specific embodiment
Now in conjunction with embodiment, the invention will be further described:
1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid for thymopeptide-5 molecule (TP5) trace
([HeVIM] Cl) function monomer, the molecular structure of ionic liquid are as follows:。
Step is:
Step 1: the 1- vinyl imidazole by dry 34ml2- chlorethanol and newly distilled is added by 1:1.2 (molar ratio)
In 100ml three-necked flask, rate of addition is controlled, is added in 30~40min.In 80 DEG C, stirred under nitrogen atmosphere reaction 18~
For 24 hours, faint yellow glutinous thick liquid is obtained.
Step 2: faint yellow glutinous thick liquid obtained by step 1 is washed 3~5 times, each 20mL with ether, it is not anti-to remove
The 1- vinyl imidazole answered.
Step 3: product dry 10~12h in 50 DEG C of electric vacuum drying oven after washing obtained by step 2 is obtained
To 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid ([HeVIM] Cl) function monomer of pale yellow transparent.
Embodiment 1: the 1- vinyl miaow that 34mL (0.5mol) dry ethylene chlorhydrin and 52mL (0.6mol) are newly distilled
Azoles is added into 100ml three-necked flask, controls rate of addition, adds in 30min.In 80 DEG C, stirred under nitrogen atmosphere reacts
For 24 hours, faint yellow glutinous thick liquid is obtained.And washed 5 times with the ether of 100mL, to remove unreacted 1- vinyl imidazole, most
Afterwards, the dry 10h in 50 DEG C of electric vacuum drying oven, obtains [HeVIM] Cl of pale yellow transparent.
Using Fluorescence Spectrometer, measured under conditions of 20 DEG C of excitation wavelength 260nm, 260~440nm of launch wavelength, from
Sub- liquid functional monomer [HeVIM] Cl results in the fluorescent quenching of TP5 by a relatively large margin, and strong interaction has occurred in the two, print
The mark factor reaches 2.08.
Embodiment 2: the 1- vinyl miaow that 34mL (0.5mol) dry ethylene chlorhydrin and 52mL (0.6mol) are newly distilled
Azoles is added into 100ml three-necked flask, controls rate of addition, adds in 30min.In 80 DEG C, stirred under nitrogen atmosphere reacts
For 24 hours, faint yellow glutinous thick liquid is obtained.And washed 5 times with the ether of 100mL, to remove unreacted 1- vinyl imidazole, most
Afterwards, the dry 10h in 50 DEG C of electric vacuum drying oven, obtains [HeVIM] Cl of pale yellow transparent.
Using the ultraviolet-visible spectrometer of model U-3010, at 25 DEG C, wavelength measures between 190~320nm.Work as TP5
When being respectively 1:20,1:45 with ionic liquid function monomer [HeVIM] Cl amount ratio (molar ratio), the two interacts ultraviolet
Absorption spectrum maximum absorption band wavelength is respectively 238.4nm, 243.9nm, and red shift occurs.When amount ratio is 1:45, [HeVIM] Cl
Strong interaction occurs with TP5.
Embodiment 3: the 1- vinyl miaow that 34mL (0.5mol) dry ethylene chlorhydrin and 52mL (0.6mol) are newly distilled
Azoles is added into 100ml three-necked flask, controls rate of addition, adds in 30min.In 80 DEG C, stirred under nitrogen atmosphere reacts
For 24 hours, faint yellow glutinous thick liquid is obtained.And washed 5 times with the ether of 100mL, to remove unreacted 1- vinyl imidazole, most
Afterwards, the dry 10h in 50 DEG C of electric vacuum drying oven, obtains [HeVIM] Cl of pale yellow transparent.
Using the ultraviolet-visible spectrometer of model U-3010, at 25 DEG C, wavelength measures between 190~320nm.Work as TP5
When being respectively 1:45,1:50 with ionic liquid function monomer [HeVIM] Cl amount ratio (molar ratio), the two interacts ultraviolet
Absorption spectrum maximum absorption band wavelength is respectively 243.9nm and 242.6nm, and blue shift occurs.When amount ratio is 1:50, [HeVIM]
Weaker interaction occurs for Cl and TP5.
Embodiment 4: the 1- vinyl miaow that 34mL (0.5mol) dry ethylene chlorhydrin and 52mL (0.6mol) are newly distilled
Azoles is added into 100ml three-necked flask, controls rate of addition, adds in 30min.In 80 DEG C, stirred under nitrogen atmosphere reacts
For 24 hours, faint yellow glutinous thick liquid is obtained.And washed 5 times with the ether of 100mL, to remove unreacted 1- vinyl imidazole, most
Afterwards, the dry 10h in 50 DEG C of electric vacuum drying oven, obtains [HeVIM] Cl of pale yellow transparent.
Using the ultraviolet-visible spectrometer of model U-3010, at 25 DEG C, wavelength measures between 190~320nm.Work as TP5
When being respectively 1:10,1:50 with ionic liquid function monomer [HeVIM] Cl amount ratio (molar ratio), the two interacts ultraviolet
Absorption spectrum maximum absorption band wavelength is respectively 235.9nm, 242.6nm, and red shift occurs.When amount ratio is 1:10, [HeVIM] Cl
Weaker interaction occurs with TP5.
Claims (6)
1. a kind of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer, it is characterised in that: point of ionic liquid
Minor structure are as follows:
The preparation method of 1- described in a kind of claim 1 2. (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer,
It is characterized by the following steps:
Step 1: ethylene chlorhydrin being mixed with 1- vinyl imidazole 1:1.2 molar ratio, in 80 DEG C, stirred under nitrogen atmosphere reacts 18
~for 24 hours, obtain faint yellow glutinous thick liquid；
Step 2: faint yellow glutinous thick liquid obtained by step 1 being washed 3~5 times with ether, to remove unreacted 1- vinyl
Imidazoles；
Step 3: product dry 10~12h in 50 DEG C of electric vacuum drying oven after washing obtained by step 2 is obtained light
1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid ([HeVIM] Cl) function monomer of yellow transparent.
3. the preparation method of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer according to claim 2,
It is characterized by: the hybrid mode of the ethylene chlorhydrin and 1- vinyl imidazole are as follows: enter mixing liquid using dropwise addition mode
In three-necked flask.
4. the preparation method of 1- (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer according to claim 3,
It is characterized by: the rate of addition of every part of mixing liquid is 30~40min completion.
The preparation side of the 1- according to Claims 2 or 3 5. (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer
Method, it is characterised in that: the ethylene chlorhydrin is dried.
The preparation side of the 1- according to Claims 2 or 3 6. (2- ethoxy) -3- vinyl imidazole chloride ion liquid function monomer
Method, it is characterised in that: the 1- vinyl imidazole is distilled.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824596A (en) * | 2019-03-08 | 2019-05-31 | 杭州华樾新材料有限公司 | The preparation method of ionic liquid |
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| CN102513158A (en) * | 2011-12-05 | 2012-06-27 | 上海师范大学 | Method for preparing ethylene carbonate through continuous heterogeneous catalysis and catalyst |
| CN105175342A (en) * | 2015-10-14 | 2015-12-23 | 大连工业大学 | Ionic liquid and method for homogeneous phase-modified reed-reinforced PE (polyethylene) composite material thereof |
| CN108707209A (en) * | 2018-05-17 | 2018-10-26 | 辽宁大学 | The preparation method and its swellability of response polymeric ionic liquid hydrogel are tested |
| CN109021173A (en) * | 2018-06-21 | 2018-12-18 | 西北工业大学 | A kind of preparation method of thymopeptide-5 molecular engram core-shell particles |
-
2018
- 2018-07-04 CN CN201810724749.9A patent/CN108997219A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102513158A (en) * | 2011-12-05 | 2012-06-27 | 上海师范大学 | Method for preparing ethylene carbonate through continuous heterogeneous catalysis and catalyst |
| CN105175342A (en) * | 2015-10-14 | 2015-12-23 | 大连工业大学 | Ionic liquid and method for homogeneous phase-modified reed-reinforced PE (polyethylene) composite material thereof |
| CN108707209A (en) * | 2018-05-17 | 2018-10-26 | 辽宁大学 | The preparation method and its swellability of response polymeric ionic liquid hydrogel are tested |
| CN109021173A (en) * | 2018-06-21 | 2018-12-18 | 西北工业大学 | A kind of preparation method of thymopeptide-5 molecular engram core-shell particles |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109824596A (en) * | 2019-03-08 | 2019-05-31 | 杭州华樾新材料有限公司 | The preparation method of ionic liquid |
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Application publication date: 20181214 |