CN102585040A - Beta-cyclodextrin derivative based on annular alkamine as well as preparation method and application of beta-cyclodextrin derivative - Google Patents
Beta-cyclodextrin derivative based on annular alkamine as well as preparation method and application of beta-cyclodextrin derivative Download PDFInfo
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Abstract
The invention discloses a beta-cyclodextrin derivative based on annular alkamine as well as a preparation method and an application of the beta-cyclodextrin derivative. The beta-cyclodextrin derivative is mono (6-(2-hydroxyl hexanaphthene amino)-6-deoxidation)-beta-cyclodextrin (CD-1), mono (6-(3-hydroxyl hexanaphthene amino)-6-deoxidation)-beta-cyclodextrin (CD-2), mono (6-(4-hydroxyl hexanaphthene amino)-6-deoxidation)-beta-cyclodextrin (CD-3), mono (6-(2-hydroxyl cyclopentyl amino)-6-deoxidation)-beta-cyclodextrin (CD-4) and mono (6-(3-hydroxyl-4-amino tetrahydrofuran)-6-deoxidation)-beta-cyclodextrin (CD-5). The beta-cyclodextrin derivative can be prepared from mono (6-O-p-tosyl group)-beta-cyclodextrin and corresponding annular alkamine to take nucleophilic substitution reaction in polar aprotic solvents. A synthetic method has the advantages that the operation is simple, the reaction condition is mild, the yield is high, and the like. The beta-cyclodextrin derivative can be used as a water-soluble ligand of metal imitation enzymes to be applied to water phase metal catalytic organic synthesis, water phase molecular recognition and water phase photosensitive materials.
Description
Technical field
The present invention relates to a kind of based on cyclic amino alcohols
β-cyclodextrin derivative and its production and application, belong to catalysis organic synthesis field.
Background technology
Schardinger dextrins (cyclodextrin, be called for short CD) be by
D-(+)-glucopyranose units is passed through
α-1, the cyclic oligosaccharide that the 4-glycosidic link is formed by connecting is the truncated cones shape, has the special construction and the character of " inner chamber is hydrophobic, and outer wall is hydrophilic ".In its molecule, has only a kind of functional group of hydroxyl; Be prone to form intramolecular hydrogen bond between hydroxyl; Thereby the cyclodextrin molecular structure has very strong rigidity, and when interacting with the guest molecule with different shape and functional group, the structure of Schardinger dextrins is difficult to take place corresponding change in topology.Simultaneously, Schardinger dextrins is only soluble in water and the strong polar organic solvent of minority, limited its application in organic solvent (
Chem. Rev. 2003,
103, 4147).For physics and the chemical property that changes Schardinger dextrins, can be optionally the hydroxyl of Schardinger dextrins be carried out chemically modified, hydroxyl is changed into target functional group, and then be built into imitative enzyme of various manual works or the imitative enzyme of artificial metal.
Based on the imitative enzyme of artificial metal that Schardinger dextrins is constructed, mainly be with the part of the cyclodextrin derivative that passes through modification as metals ion, by the inclusion of cyclodextrin cavity and substrate, organic synthesis is transferred to water from organic phase, environmental protection.Inclusion effect simultaneously also furthered relatively substrate and catalytic active center distance and fixed the relative position of the two, often can significantly improve speed of reaction, regioselectivity and the enantioselectivity of organic synthesis.
Breslow etc. are respectively to have two or four
βThe unitary derivatives of porphyrin of-Schardinger dextrins is as the part of metal ions M n (III), is applied to the hydroxylating of catalysis sterid as the cytochrome P-450 analogue enztme, the realization of highly selective the hydroxylation of sterid C-9 position (
J. Am. Chem. Soc. 1997,
119, 4535.;
Angew. Chem. Int. Edit. 2000,
39, 2692.).Cyclic amino alcohols is compared with general straight chain amino alcohol, and is water-soluble relatively poor, sterically hindered big between amino and the hydroxyl, through its modification
β-Schardinger dextrins can not only be well and metals ion generation complexing, and modification group has stronger rigidity, and chiral induction is effective.Therefore, exploitation synthesis of cyclic amino alcohol is modified
β-Schardinger dextrins has stronger theoretical investigation value and using value as the imitative enzyme water soluble ligand of metal.
Summary of the invention
The object of the present invention is to provide a kind of based on cyclic amino alcohols
β-cyclodextrin derivative.
Provided by the invention a kind of based on cyclic amino alcohols
β-cyclodextrin derivative is modified for the 2-Trans-4-Amino Cyclohexanol
β-Schardinger dextrins (CD-1), 3-Trans-4-Amino Cyclohexanol are modified
β-Schardinger dextrins (CD-2), 4-Trans-4-Amino Cyclohexanol are modified
β-Schardinger dextrins (CD-3), 2-amino cyclopentyl alcohol are modified
β-Schardinger dextrins (CD-4) and 3-amino-4-hydroxy THF are modified
β-Schardinger dextrins (CD-5), it is modified the position and is
β-Schardinger dextrins C-6 position, modification group are cyclic amino alcohols, and its structural formula is as follows:
CD-1 CD-2 CD-3 CD-4 CD-5
Wherein:
For
β-Schardinger dextrins parent fraction.
It is said based on cyclic amino alcohols that the present invention also provides
βThe preparation method of-cyclodextrin derivative said method comprising the steps of: will single (6-
O-
p-tosyl group)-
β-Schardinger dextrins and cyclic amino alcohols are dissolved in the anhydrous polar aprotic solvent, under nitrogen atmosphere, under temperature of reaction, react; Behind gained reaction mixture cool to room temperature, slowly be added drop-wise in the acetone suction filtration; With absolute ethanol washing gained solid; And in pure water, carry out recrystallization, respectively through acetone, washing, make product after the vacuum-drying.
Above-mentioned based on cyclic amino alcohols
βAmong the preparation method of-cyclodextrin derivative, described list (6-
O-
p-tosyl group)-
βThe mol ratio of-Schardinger dextrins and cyclic amino alcohols is 1:1 ~ 1:500; Said anhydrous polar aprotic solvent is acetonitrile, tetramethylene sulfone, hexamethylphosphoramide, N, a kind of in dinethylformamide and the DMSO 99.8MIN.; Temperature of reaction is 50 ° of C ~ 160 ° C; Reaction times is 6.0h ~ 96.0h.
It is said based on cyclic amino alcohols that the present invention also provides
βThe application of-cyclodextrin derivative should
βThe water soluble ligand that-cyclodextrin derivative can be used as the imitative enzyme of metal is applied to aqueous metal catalysis organic synthesis, water molecular recognition or water sensitive materials aspect.
In above-mentioned application, preferably should
β-cyclodextrin derivative is applied to it is characterized in that may further comprise the steps in the asymmetric oxidation of aqueous metal catalysis thioether: will
β-cyclodextrin derivative CD-1 ~ CD-5 and metal-salt are dissolved in CH
3In the COONa-HCl damping fluid, stir under the room temperature, add thioether then, reaction mixture is stirred, add 30% H
2O
2The aqueous solution, CH
2Cl
2Extraction also merges organic layer, and the saturated NaCl aqueous solution is washed gained organic layer, anhydrous Na
2SO
4Drying, the decompression precipitation gets yellow oily liquid, and described thioether is the compound with following formula:
Wherein, R
1And R
2Be selected from methyl, ethyl, propyl group, butyl, sec.-propyl, the tertiary butyl, phenyl, 1-naphthyl, 2-naphthyl, methoxyl group, oxyethyl group, hydroxyl, sulfydryl, amino, methylamino-, ethylamino, dimethylamino, 1-hydroxyethyl, chlorine, bromine, iodine etc., R
1, R
2Can be identical, also can be different.
Beneficial effect of the present invention is mainly reflected in: relate to based on cyclic amino alcohols
β-cyclodextrin derivative CD-1 ~ CD-5 novel structure, its synthetic route is simple, and yield is high, and applicability is wide, can carry out ligand complex with multiple metals ion, in the organic asymmetric catalysis synthesis of catalysis, shows excellent enantioselectivity, product
EeThe % value is high, and is easy to reclaim.
Embodiment
Below in conjunction with specific embodiment the present invention is described further, but protection scope of the present invention is not limited in this:
What embodiment 1-6 explained is cyclic amino alcohols
βThe application of-cyclodextrin derivative in aqueous metal catalysis organic synthesis.
What embodiment 7 explained is cyclic amino alcohols
βThe application of-cyclodextrin derivative in water molecular recognition or water sensitive materials.
Embodiment 1
In 250mL eggplant shaped reaction bottle, with the single (6-of 32.23g (25.0mmol)
O-
p-tosyl group)-
β-Schardinger dextrins and 2.88g (25.0mmol) 2-Trans-4-Amino Cyclohexanol is dissolved among the anhydrous HMPA of 100mL, in N
2Under the atmosphere, 120 ° of C stirring reaction 60.0h.Behind gained reaction mixture cool to room temperature, slowly be added drop-wise in the 400mL acetone suction filtration; The 200mL absolute ethyl alcohol is washed the gained solid, recrystallization secondary in 2 * 150mL water, and the gained solid washed by 100mL acetone; The 50mL washing; Vacuum-drying 3.0h under 120 ° of C gets white solid (CD-1) 27.87g, yield 90.48%.
CD-1: m.p. >265°C;
1H NMR(DO
2, 400 MHz)
δ: 5.25~5.17(m, 7H), 4.06~3.88(m, 26H), 3.82~3.67(m, 14H), 3.53(t, 1H), 3.18(d, 1H), 2.98~2.93(m, 1H), 2.74~2.66(m, 1H), 1.89~1.33 ppm (m, 8H);
13C NMR (DMSO-
d 6 , 400 MHz)
δ: 101.94~101.71, 82.81, 82.00~81.40, 72.88~71.87, 70.77, 67.30, 59.73, 58.15, 46.08, 30.64, 26.79, 22.39, 20.97 ppm; MS (ESI):
m/z: 1232.4([M+1]
+), 1254.5([M+Na]
+).
Embodiment 2
In 250mL eggplant shaped reaction bottle, with the single (6-of 32.23g (25.0mmol)
O-
p-tosyl group)-
β-Schardinger dextrins and 2.88g (25.0mmol) 3-Trans-4-Amino Cyclohexanol is dissolved among the anhydrous HMPA of 100mL, in N
2Under the atmosphere, 120 ° of C stirring reaction 60.0h.Behind gained reaction mixture cool to room temperature, slowly be added drop-wise in the 400mL acetone suction filtration; The 200mL absolute ethyl alcohol is washed the gained solid, recrystallization secondary in the 2 150mL water, and the gained solid washed by 100mL acetone; The 50mL washing; Vacuum-drying 3.0h under 120 ° of C gets white solid (CD-2) 28.45g, yield 92.36%.
CD-2: m.p. >265°C;
1H NMR (DO
2, 400 MHz)
δ: 5.18~5.07(m, 7H), 4.14~3.80(m, 26H), 3.70~3.58(m, 14H), 3.48~3.38(m, 1H), 3.22~3.12(m, 1H), 2.93~2.76(m, 1H), 2.65~2.55(m, 1H), 2.22~0.98 ppm (m, 8H); MS (ESI):
m/z: 1232.4([M+1]
+), 1254.4([M+Na]
+).
Embodiment 3
In 250mL eggplant shaped reaction bottle, with the single (6-of 32.23g (25.0mmol)
O-
p-tosyl group)-
β-Schardinger dextrins and 2.88g (25.0mmol) 4-Trans-4-Amino Cyclohexanol is dissolved among the anhydrous HMPA of 100mL, in N
2Under the atmosphere, 120 ° of C stirring reaction 60.0h.Behind gained reaction mixture cool to room temperature, slowly be added drop-wise in the 400mL acetone suction filtration; The 200mL absolute ethyl alcohol is washed the gained solid, recrystallization secondary in 2 * 150mL water, and the gained solid washed by 100mL acetone; The 50mL washing; Vacuum-drying 3.0h under 120 ° of C gets white solid (CD-3) 28.22g, yield 91.61%.
CD-3: m.p. >275°C;
1H NMR (DO
2, 400 MHz)
δ: 5.18~5.09(m, 7H), 3.98~3.84(m, 26H), 3.71~3.58(m, 14H), 3.47(t, 1H), 3.19(d, 1H), 2.84(t, 1H), 2.57(t, 1H), 2.02~1.95(m, 4H), 1.36~1.18 ppm(m, 4H); MS (ESI):
m/z: 1232.5([M+1]
+), 1254.5([M+Na]
+).
Embodiment 4
In 250mL eggplant shaped reaction bottle, with the single (6-of 32.23g (25.0mmol)
O-
p-tosyl group)-
β-Schardinger dextrins and 2.53g (25.0mmol) 2-amino cyclopentyl alcohol is dissolved among the anhydrous HMPA of 100mL, in N
2Under the atmosphere, 120 ° of C stirring reaction 60.0h.Behind gained reaction mixture cool to room temperature, slowly be added drop-wise in the 400mL acetone suction filtration; The 200mL absolute ethyl alcohol is washed the gained solid, recrystallization secondary in 2 * 150mL water, and the gained solid washed by 100mL acetone; The 50mL washing; Vacuum-drying 3.0h under 120 ° of C gets white solid (CD-4) 27.51g, yield 90.34%.
CD-4: m.p. >265°C;
1H NMR (DO
2, 400 MHz)
δ: 5.11~5.04(m, 7H), 3.97~3.79(m, 26H), 3.70~3.53(m, 14H), 3.45~3.35(m, 1H), 3.18~3.01(m, 1H), 2.95~2.88(m, 1H), 2.83~2.76(m, 1H), 2.03~1.33 ppm (m, 6H); MS (ESI):
m/z: 1218.4([M+1]
+), 1240.4([M+Na]
+).
Embodiment 5
In 250mL eggplant shaped reaction bottle, with the single (6-of 32.23g (25.0mmol)
O-
p-tosyl group)-
β-Schardinger dextrins and 2.58g (25.0mmol) 3-amino-4-hydroxy THF is dissolved among the anhydrous HMPA of 100mL, in N
2Under the atmosphere, 120 ° of C stirring reaction 60.0h.Behind gained reaction mixture cool to room temperature, slowly be added drop-wise in the 400mL acetone suction filtration; The 200mL absolute ethyl alcohol is washed the gained solid, recrystallization secondary in 2 * 150mL water, and the gained solid washed by 100mL acetone; The 50mL washing; Vacuum-drying 3.0h under 120 ° of C gets white solid (CD-5) 28.36g, yield 92.98%.
CD-5: m.p. >250°C;
1H NMR (DO
2, 400 MHz)
δ: 5.09~5.06(m, 7H), 4.31~4.23(m, 1H), 4.13~4.08(m, 1H), 3.98~3.85(m, 26H), 3.75~3.70(m, 1H), 3.66~3.55(m, 14H), 3.50~3.44(m, 1H), 3.25~3.21(m, 1H), 3.13~3.07(m, 1H), 2.93~2.79(m, 1H), 2.58 ppm(s, 1H); MS (ESI):
m/z: 1220.3([M+1]
+), 1242.4([M+Na]
+).
Embodiment 6
In two mouthfuls of Kjeldahl flasks of 250mL, with 10mmol
β-cyclodextrin derivative CD-1 ~ CD-5 and 0.85g (5.0mmol) CuCl
22H
2O is dissolved in 100mL pH=9.5 4.0M CH
3In the COONa-HCl damping fluid, stir 1.0h under the room temperature.Add aminomethyl phenyl thioether 62.11g (500mmol) then, stir 1.0h under the room temperature.Reaction mixture is placed-20 ° of C stir down, add 50mL 30% H
2O
2The aqueous solution, stirring reaction 3.0h under-20 ° of C.3 * 100mL CH
2Cl
2Extraction also merges organic layer, and the saturated NaCl aqueous solution of 100mL is washed gained organic layer, anhydrous Na
2SO
4Drying, the decompression precipitation gets yellow oily liquid.HPLC analyzes (V
Normal hexane: V
Virahol=4:1,0.9mL/min, 254nm).Yield, 96%.
ee%，92%(
S)。
Embodiment 7
At NaOH-KH
2PO
4In the damping fluid, fixing
pThe concentration (5.0 * 10 of-tolyl aldehyde
-5Mol/L or 4.0 * 10
-5Mol/L),
βThe concentration of-cyclodextrin derivative CD-1 ~ CD-5 gets (0.2 * 10 successively
-3Mol/L, 0.4 * 10
-3Mol/L, 0.6 * 10
-3Mol/L, 0.8 * 10
-3Mol/L and 1.0 * 10
-3Mol/L) and (1.0 * 10
-3Mol/L, 2.0 * 10
-3Mol/L, 3.0 * 10
-3Mol/L, 4.0 * 10
-3Mol/L and 5.0 * 10
-3Mol/L), leave standstill about 36.0 h under 25 ° of C after, with respective concentration
β-cyclodextrin derivative solution is reference, measures its uv absorption spectrum and variation successively.
Fixing
pThe concentration of-tolyl aldehyde is 5.0 * 10
-5Mol/L, the concentration of CD-1 gets 0,1.0, and 2.0,3.0,4.0,5.0 * 10
-3Mol/L measures successively
pThe uv absorption spectrum of-tolyl aldehyde.At maximum absorption 261nm place, uv-absorbing is followed successively by 0.8093,0.7880, and 0.7787,0.7743,0.7717 and 0.7687, explained that uv absorption spectrum intensity descends along with the increase of CD-1 concentration successively.This be since CD-1 to aqueous phase
pThe molecular recognition of-tolyl aldehyde has caused aqueous phase
pThe variation of-tolyl aldehyde uv absorption spectrum.
Claims (9)
1. one type based on cyclic amino alcohols
β-cyclodextrin derivative is characterized in that comprising: the 2-Trans-4-Amino Cyclohexanol is modified
β-Schardinger dextrins (CD-1), 3-Trans-4-Amino Cyclohexanol are modified
β-Schardinger dextrins (CD-2), 4-Trans-4-Amino Cyclohexanol are modified
β-Schardinger dextrins (CD-3), 2-amino cyclopentyl alcohol are modified
β-Schardinger dextrins (CD-4) and 3-amino-4-hydroxy THF are modified
β-Schardinger dextrins (CD-5), it is modified the position and is
β-Schardinger dextrins C-6 position, modification group are cyclic amino alcohols, and its structural formula is as follows:
CD-1 CD-2 CD-3 CD-4 CD-5
Wherein:
For
β-Schardinger dextrins parent fraction.
2. a claim 1 is said based on cyclic amino alcohols
βThe preparation method of-cyclodextrin derivative is characterized in that may further comprise the steps: will single (6-
O-
p-tosyl group)-
β-Schardinger dextrins and cyclic amino alcohols are dissolved in the anhydrous polar aprotic solvent, under nitrogen atmosphere, under temperature of reaction, react; Behind gained reaction mixture cool to room temperature, slowly be added drop-wise in the acetone suction filtration; With absolute ethanol washing gained solid; And in pure water, carry out recrystallization, respectively through acetone, washing, make product after the vacuum-drying.
3. preparation method according to claim 2 is characterized in that, said list (6-
O-
p-tosyl group)-
βThe mol ratio of-Schardinger dextrins and cyclic amino alcohols is 1:1 ~ 1:500.
4. preparation method according to claim 2 is characterized in that, said anhydrous polar aprotic solvent is acetonitrile, tetramethylene sulfone, hexamethylphosphoramide, N, a kind of in dinethylformamide and the DMSO 99.8MIN..
5. preparation method according to claim 2 is characterized in that temperature of reaction is 50 ° of C ~ 160 ° C, and the reaction times is 6.0h ~ 96.0h.
6. claim 1 is described based on cyclic amino alcohols
βThe application of-cyclodextrin derivative in aqueous metal catalysis organic synthesis, water molecular recognition or water sensitive materials.
7. application according to claim 6 is characterized in that, and is said
βThe application of-cyclodextrin derivative in aqueous metal catalysis thioether asymmetric oxidation.
8. application according to claim 7 is characterized in that may further comprise the steps: will
β-cyclodextrin derivative CD-1 ~ CD-5 and metal-salt are dissolved in CH
3In the COONa-HCl damping fluid, stir under the room temperature, add thioether then, reaction mixture is stirred, add 30% H
2O
2The aqueous solution, CH
2Cl
2Extraction also merges organic layer, and the saturated NaCl aqueous solution is washed gained organic layer, anhydrous Na
2SO
4Drying, the decompression precipitation gets yellow oily liquid.
9. according to claim 7 or 8 described application; It is characterized in that described thioether is the compound with following formula:
Wherein, R
1And R
2Be selected from methyl, ethyl, propyl group, butyl, sec.-propyl, the tertiary butyl, phenyl, 1-naphthyl, 2-naphthyl, methoxyl group, oxyethyl group, hydroxyl, sulfydryl, amino, methylamino-, ethylamino, dimethylamino, 1-hydroxyethyl, chlorine, bromine and iodine, R
1, R
2Can be identical, also can be different.
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| CN105175580A (en) * | 2015-10-14 | 2015-12-23 | 中山大学 | Beta-cyclodextrin derivatives based on amino acid reduced product alkamine and preparation method and application of beta-cyclodextrin derivative |
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| CN101195662A (en) * | 2007-12-20 | 2008-06-11 | 山东大学 | 6-(2-glucosyl amido)-beta- cyclodextrin derivant and method for producing the same |
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2012
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| CN101195662A (en) * | 2007-12-20 | 2008-06-11 | 山东大学 | 6-(2-glucosyl amido)-beta- cyclodextrin derivant and method for producing the same |
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| 《Carbohydrate Research》 20110922 K. Martina et al Synthesis of water-soluble multidentate aminoalcohol b-cyclodextrin 第2677-2682页 1-9 第346卷, * |
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| CN105175580A (en) * | 2015-10-14 | 2015-12-23 | 中山大学 | Beta-cyclodextrin derivatives based on amino acid reduced product alkamine and preparation method and application of beta-cyclodextrin derivative |
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