CN106008754A - Mono-(6-propargylamino-deoxy)-beta-cyclodextrin function monomer and preparation method thereof - Google Patents
Mono-(6-propargylamino-deoxy)-beta-cyclodextrin function monomer and preparation method thereof Download PDFInfo
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- CN106008754A CN106008754A CN201610367202.9A CN201610367202A CN106008754A CN 106008754 A CN106008754 A CN 106008754A CN 201610367202 A CN201610367202 A CN 201610367202A CN 106008754 A CN106008754 A CN 106008754A
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- schardinger dextrin
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000000178 monomer Substances 0.000 title abstract description 27
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims abstract description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- -1 Methyl benzenesulfonyl Chemical group 0.000 claims description 22
- 239000002244 precipitate Substances 0.000 claims description 11
- 238000001556 precipitation Methods 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 abstract description 8
- 229920000858 Cyclodextrin Polymers 0.000 abstract description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000001212 derivatisation Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000012644 addition polymerization Methods 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 239000001116 FEMA 4028 Substances 0.000 abstract 4
- 229960004853 betadex Drugs 0.000 abstract 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 229920000344 molecularly imprinted polymer Polymers 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 238000000605 extraction Methods 0.000 description 6
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 5
- 229960003500 triclosan Drugs 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/14—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
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- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention discloses a mono-(6-propargylamino-deoxy)-beta-cyclodextrin function monomer and a preparation method thereof, and belongs to the technical field of organic synthesis. Mono-(6-propargylamino-deoxy)-beta-cyclodextrin is synthesized from mono-6-O-(p-methylphenylsulfonyl)-beta-cyclodextrin with propargylamine as a derivatization reagent. The structure of the mono-(6-propargylamino-deoxy)-beta-cyclodextrin contains a terminal acetylene link, and the mono-(6-propargylamino-deoxy)-beta-cyclodextrin can participate in addition polymerization as a function monomer to prepare high-molecular polymers. The function monomer is a new compound, has not been reported yet, and has no CAS number.
Description
Technical field
The present invention relates to a kind of list-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-function monomer and preparation method thereof, belong to
Technical field of organic synthesis.
Background technology
Function monomer is the organic compound that a class is special, does not contain only hydroxyl, amido, carboxyl, ester in its molecular structure
The specific functional groups such as base, can be with other molecule generation intermolecular interactions, possibly together with the double or triple bonds of polyreaction can be participated in, and can
To participate in macromolecular polymerization reaction, thus prepare and there is special adsorbing high molecular polymer[1].At present, extensively make
Function monomer have similar the spreading out of acrylic acid, methacrylic acid, acrylamide, 4-vinylpridine, styrene and structure thereof
Biological etc..Cyclodextrin is the compound that a class formation is special, especially most commonly seen with beta-schardinger dextrin-, its molecular structure tool in the form of a ring
There is Inclusion property, and hydroxyls numerous in molecule can carry out selective derivatization[2].Beta-schardinger dextrin-class function monomer is that a class is new
Emerging function monomer[3], but, these function monomers of report are double bond containing function monomer at present, have no the function of three keys
Monomer, the function monomer of three keys has the higher degree of polymerization and the degree of cross linking during polymerization.The present invention proposes a kind of containing alkynes
Beta-schardinger dextrin-function monomer of key and preparation method thereof, this function monomer has no report, at present without commercial prod, and without CAS
Number.
List of references:
[1] Hu little Gang, Tang Youwen. molecularly imprinted polymer Study on Preparation Technology is in progress, South China Normal University's journal,
2003, (3): 150-157.
[2] Tong Linhui. Cyclodextrin Chemistry basis and application, Beijing: Science Press, 2001:1-9.
[3] Xu Zhigang, Liu Zhimin, Shi Jielan, Lu Yao. cyclodextrin molecular engram technology and applied research thereof, chemistry examination
Agent, 2013,35 (1): 32-36.
Summary of the invention
It is an object of the invention to provide a kind of list-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-, provide it to prepare simultaneously
Method.
List of the present invention-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-, its structural formula is as follows:
。
The preparation method of list of the present invention-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-, specifically comprise the following steps that by single-
6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-(CAS 67217-55-4) is placed in flask, adds propargylamine (No. CAS
2450-71-7) reacting, reaction temperature is 65 ~ 90 DEG C, and the time is 2 ~ 6 hours, and reaction equation is as follows:
。
Naturally cool to room temperature after having reacted, add methanol and dissolve, add acetonitrile to precipitation completely, be collected by filtration white
Color precipitates, and repeats purification (i.e. methanol dissolves, then adds acetonitrile precipitation) four times, is vacuum dried product, i.e. obtain single-(6-propargylamine-
6-deoxygenates)-beta-schardinger dextrin-.
Described list-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1:160 ~ 320 with the mol ratio of propargylamine.
The invention have the benefit that
List of the present invention-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-function monomer, is (to Methyl benzenesulfonyl with list-6-O-
Base)-beta-schardinger dextrin-is raw material, using propargylamine is that derivatization reagent introduces unsaturated acetylene bond functional group.This function monomer is new
Compound, has no that document is reported, and does not has No. CAS.This function monomer can be participated in addition polymerization and prepare high molecular polymer, its ring
Dextrin group can be used as the functional group of high molecular polymer, has important Research Significance and using value.
Detailed description of the invention
Below by embodiment, the present invention is described in further detail, but protection scope of the present invention is not limited to institute
State content.
Embodiment 1
Taking 1.51g(1.171mmol) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-puts in 50mL round-bottomed flask, adds
Entering 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1 with the mol ratio of propargylamine:
200, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 85 DEG C, fully reacts 5h.After having reacted,
The solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration, weight
Multiple purification four times, is vacuum dried obtained product, weighs, productivity 83.85%.Characterization of The Products data are as follows:
IR(KBr): 3383,2927,1643,1417,1371,1245,1156,1080,1031cm-1。
1H-NMR(600MHz, CD3OD):=5.746,5.697,4.825,4.497,2.641,2.611,2.547,
2.441,2.298,2.296,2.027,2.500.
MS(ESI)m/z: 1172 [M]+、1173[M+H]+、606[M+H+K]2+。
Embodiment 2
Taking 1.51g(1.171mmol) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-puts in 50mL round-bottomed flask, adds
Entering 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1 with the mol ratio of propargylamine:
200, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 85 DEG C, fully reacts 4h.After having reacted,
The solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration, weight
Multiple purification four times, is vacuum dried obtained product, weighs, productivity 78.95%.
Embodiment 3
Taking 1.51g(1.171mmol) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-puts in 50mL round-bottomed flask, adds
Entering 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1 with the mol ratio of propargylamine:
200, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 85 DEG C, fully reacts 2h.After having reacted,
The solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration, weight
Multiple purification four times, is vacuum dried obtained product, weighs, productivity 48.08%.
Embodiment 4
Taking 1.887g(1.464mmol) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-puts in 50mL round-bottomed flask, adds
Entering 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1 with the mol ratio of propargylamine:
160, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 75 DEG C, fully reacts 4h.After having reacted,
The solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration, weight
Multiple purification four times, is vacuum dried obtained product, weighs, productivity 69.20%.
Embodiment 5
Taking 0.9435g(0.732mmol) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-puts in 50mL round-bottomed flask,
Adding 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-with the mol ratio of propargylamine is
1:320, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 75 DEG C, fully reacts 4h.Reaction completes
After, the solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration,
Repeat purification four times, obtained product is vacuum dried, weighs, productivity 64.44%.
Embodiment 6
Taking 1.51g(1.171mmol) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-puts in 50mL round-bottomed flask, adds
Entering 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1 with the mol ratio of propargylamine:
200, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 85 DEG C, fully reacts 6h.After having reacted,
The solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration, weight
Multiple purification four times, is vacuum dried obtained product, weighs, productivity 56.48%.
Embodiment 7
Taking 1.51g(1.171mmol) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-puts in 50mL round-bottomed flask, adds
Entering 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1 with the mol ratio of propargylamine:
200, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 65 DEG C, fully reacts 4h.After having reacted,
The solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration, weight
Multiple purification four times, is vacuum dried obtained product, weighs, productivity 78.95%.
Embodiment 8
Take single-6-O-(to Methyl benzenesulfonyl the base)-beta-schardinger dextrin-of 1.51g (1.171mmol) to put in 50mL round-bottomed flask, add
Entering 15mL propargylamine (0.234mol), single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1 with the mol ratio of propargylamine:
200, and flask is placed in water-bath, upper termination condensation reflux unit, it is warming up to 90 DEG C, fully reacts 4h.After having reacted,
The solution obtained is cooled to room temperature, adds methanol and dissolve, add acetonitrile the most again to precipitation completely, white precipitate is collected by filtration solid
Body, repeats purification four times, is vacuum dried by obtained product, weighs, productivity 67.64%.
Embodiment 9
List-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-function monomer of synthesis is for the system of triclosan molecularly imprinted polymer
Standby.Take 0.0625mmol triclosan, 0.25mmol mono--(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-is dissolved in 2.5mL dimethyl
In sulfoxide, place 12h；Add 3.75mmol ethylene glycol dimethacrylate, add 20mg azodiisobutyronitrile, ultrasonic,
Logical nitrogen, deoxygenation, then pipette (internal diameter about 1.0mm) in the capillary tube that one end blocks, inserts one end-blocking more carefully outside
The capillary tube (external diameter about 0.5mm) in footpath, sealing, is polymerized 24h at 60 DEG C of heating in water bath；After reaction terminates, wash with methanol solution
Stripper plate molecule and impurity, obtain triclosan molecularly imprinted polymer.Non-imprinted polymer prepare same molecularly imprinted polymer
Preparation method, but be added without template molecule.
For the molecule that contrast is prepared containing acetylene bond beta-schardinger dextrin-function monomer and the beta-schardinger dextrin-function monomer Han ethylene linkage further
The extracting power of imprinted polymer, separately taking list-(6-is to vinyl benzene sulfonyl)-beta-schardinger dextrin-is that function monomer is by above-mentioned side
Method prepares triclosan molecularly imprinted polymer.
Prepared molecularly imprinted polymer and non-imprinted polymer are used for the extractive analysis of triclosan.Extracting process is:
Extractant is water, and extraction time is 120min, and desorption solvent is chromatograph methanol, and ultrasonic desorption time is 10min, extracts concentration
For 0.050mg/L, extraction volume is 20mL, and extraction mode is stirring extraction, and rotating speed is 500rpm, and ultrasonic stripping liquid volume is
200μL.Liquid chromatography detecting method is: flowing is mutually for methanol: 0.2% phosphoric acid (78:22)；Detection wavelength: 280nm；Flow velocity:
1mL/min；Column temperature: 30 DEG C；Sample size: 20 μ L.Chromatographic column is C18 post (250mm × 4.6mm).
Analysis result shows: the trichlorine prepared based on list-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-function monomer is estranged
Sub-imprinted polymer, has selective absorption extracting power at aqueous phase solution to template molecule, and selectivity factor is 1.64；And with
List-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-is molecularly imprinted polymer prepared by function monomer, its extraction quantity be with single-
(6-is to vinyl benzene sulfonyl)-beta-schardinger dextrin-is 1.76 times that function monomer prepares molecularly imprinted polymer extraction quantity, result
Also indicate that acetylene bond cyclodextrin function monomer has more preferable effect of extracting.
Claims (5)
1. list-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-, structural formula is as follows:
。
2. prepare the method for list-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-described in claim 1 for one kind, it is characterised in that bag
Include following steps:
(1) single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is placed in flask, adds propargylamine and react, reaction
Room temperature is naturally cooled to after completing；
(2) add methanol to dissolve, add acetonitrile to precipitation completely, white precipitate is collected by filtration；
(3) white precipitate is repeated step (2) purification four times, is vacuum dried product, i.e. obtain single-(6-propargylamine-6-deoxidation)-
Beta-schardinger dextrin-.
The preparation method of list the most according to claim 2-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-, it is characterised in that:
Single-6-O-(to Methyl benzenesulfonyl base)-beta-schardinger dextrin-is 1:160 ~ 320 with the mol ratio of propargylamine.
The preparation method of list the most according to claim 2-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-, it is characterised in that:
Reaction temperature is 65 ~ 90 DEG C.
The preparation method of list the most according to claim 2-(6-propargylamine-6-deoxidation)-beta-schardinger dextrin-, it is characterised in that:
Response time is 2 ~ 6 hours.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107987185A (en) * | 2017-12-04 | 2018-05-04 | 昆明理工大学 | A kind of beta-cyclodextrin function monomer of chiral radicals grafting and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102391519A (en) * | 2011-12-26 | 2012-03-28 | 北京理工大学 | Method for preparing chitosan immobilized cyclodextrin derivative from chitin |
| CN103464125A (en) * | 2013-09-18 | 2013-12-25 | 天津大学 | Preparation method and application of novel triazole bridging compound cyclodextrin chiral stationary phase |
| CN104292475A (en) * | 2014-09-30 | 2015-01-21 | 华东师范大学 | Temperature-sensitive and photosensitive dual-response polypeptide based host-guest composite intelligent hydrogel as well as preparation method and application thereof |
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