CN105175580A - Beta-cyclodextrin derivatives based on amino acid reduced product alkamine and preparation method and application of beta-cyclodextrin derivative - Google Patents
Beta-cyclodextrin derivatives based on amino acid reduced product alkamine and preparation method and application of beta-cyclodextrin derivative Download PDFInfo
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Abstract
The invention discloses beta-cyclodextrin derivatives based on amino acid reduced product alkamine and a preparation method and application of the beta-cyclodextrin derivatives. The beta-cyclodextrin derivatives are the L-phenylglycinol modified beta-cyclodextrin, D-phenylalaninol modified beta-cyclodextrin, L-phenylalaninol modified beta-cyclodextrin, L-alaninol modified beta-cyclodextrin, L-valinol modified beta-cyclodextrin, L-isoleucinol modified beta-cyclodextrin and L-leucinol modified beta-cyclodextrin. Mono-(6-O-p-tolylsulfonyl)-beta-cyclodextrin and alkamine are dissolved in an anhydrous polar aprotic solvent, and the beta-cyclodextrin derivatives are prepared in the nitrogen atmosphere. According to the method, the reaction condition is moderate, and the yield is high. The obtained beta-cyclodextrin derivatives and metal ions can be matched to be used for water-phase organocatalysis asymmetric synthesis reactions to recognize different guest molecules.
Description
Technical field
The present invention relates to a kind of based on amino acid reduzate amino alcohol beta-cyclodextrin derivative preparation method and application thereof, belong to catalysis organic synthesis field.
Background technology
Beta-cyclodextrin (β-cyclodextrin, be called for short β-CD) be a kind of by 7 glucose units by α-1, the cyclic oligomer glycan molecule that 4-glycosidic link is formed by connecting, in cone cylindrical cavity structure, and cavity inside becomes hydrophobicity space, external hydrophilic, make water-insoluble organic molecule in organic reaction system, by the hydrophobic binding effect of beta-cyclodextrin cavity, realize the catalyzed reaction (Chem.Rev.1998 in aqueous phase, 98,1743) the environmental protection object effectively reducing solvent usage quantity, is reached.Rely on non-covalent bonding force (hydrogen bond, hydrophobic forces, electrostatic attraction, ionic forces etc.), form beta-cyclodextrin-guest molecule inclusion complex, utilize chirality and the spatial positioning effect of cyclodextrin own cavity, asymmetric organic reactions can be induced to occur, and analogue enztme bound substrates carries out asymmetric catalyzed reaction.
Under basic conditions, there is certain chemical stability based on beta-cyclodextrin, constructing the supramolecule beta-cyclodextrin derivative of specific functional groups by modifying base, catalytic reaction activity and enantioselectivity can be improved.Tabushi etc. introduce Pyridoxylamine on beta-cyclodextrin, the transamination reaction of analogue enztme, in alkalescence buffer solution under normal temperature, and highly selective synthesis L-Trp and L-phenylalanine (J.Am.Chem.Soc., 1985,107,5545.).Utilize compared with amino acid whose reduzate amino alcohol modifies base with general amino alcohol, the constructional feature of chiral molecules has stronger space multistory selectivity, effective to the chiral induction of guest molecule.Therefore, synthesize such beta-cyclodextrin derivative and there is certain theoretical investigation and using value.
Summary of the invention
The object of the present invention is to provide a kind of based on amino acid reduzate amino alcohol beta-cyclodextrin derivative and preparation method thereof and application.
Provided by the invention is that L-benzene glycinol modifies beta-cyclodextrin (CD-1) based on a seed amino acid reduzate amino alcohol beta-cyclodextrin derivative, D-phenylalaninol modifies beta-cyclodextrin (CD-2), L-phenylalaninol modifies beta-cyclodextrin (CD-3), L-Propanolamine modifies beta-cyclodextrin (CD-4), L-valerian ammonia alcohol modifies beta-cyclodextrin (CD-5), L-isoleucine alcohol modifies beta-cyclodextrin (CD-6), L-leucinol modifies beta-cyclodextrin (CD-7), modify the hydroxyl that position is beta-cyclodextrin C-6, its structural formula is as follows:
Wherein,
The invention provides described based on amino acid reduzate amino alcohol beta-cyclodextrin derivative preparation method; said method comprising the steps of: single (6-O-p-tosyl group)-beta-cyclodextrin and amino alcohol are dissolved in anhydrous polar aprotic solvent; under nitrogen atmosphere; stirring reaction at the reaction temperatures, after gained reaction mixture cool to room temperature, is slowly added drop-wise in dehydrated alcohol; leave standstill; suction filtration, recrystallization in water, namely obtains product by the vacuum-drying of gained solid.
Above-mentioned based in amino acid reduzate amino alcohol beta-cyclodextrin derivative preparation method, the mol ratio of described list (6-O-p-tosyl group)-beta-cyclodextrin and amino alcohol is 1:1 ~ 1:100; Described anhydrous polar aprotic solvent is acetonitrile, or hexamethyl-phosphoramide, or DMF, or methyl-sulphoxide; Temperature of reaction is 60 ~ 150 DEG C; Reaction times is 8.0 ~ 120.0h.
Present invention also offers the described application based on amino acid reduzate amino alcohol beta-cyclodextrin derivative, beta-cyclodextrin derivative is applied to aqueous metal catalysis organic synthesis as the water soluble ligand in metalloenzyme catalysis, or aqueous phase molecular recognition aspect.
In above-mentioned application, preferentially this beta-cyclodextrin derivative is applied to the asymmetric reduction of aqueous metal catalysis aromatic ketone, its feature comprises the following steps: beta-cyclodextrin derivative and metal-salt are dissolved in HCOONa2H
2in the O aqueous solution, stirred at ambient temperature, then adds aromatic ketone, after reaction mixture stirring reaction, adds dichloromethane extraction and merges organic layer, anhydrous Na
2sO4 is dry, and obtain transparent liquid after decompression precipitation, described aromatic ketone is the compound with following formula:
Wherein R is selected from methyl, ethyl, propyl group, butyl, sec.-propyl, the tertiary butyl, phenyl, 1-naphthyl, 2-naphthyl, methoxyl group, hydroxyl, amino, methylamino-, chlorine, nitro etc.
Effect of the present invention is embodied in: based on the novel structure of amino acid reduzate amino alcohol beta-cyclodextrin derivative CD-1 ~ CD-7, synthetic method is simple, product environmental protection, yield is high, application is wide, can with metallic ion coordination, in aqueous catalysis organic synthesis, embody excellent enantioselectivity, product ee% is higher.
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 1-8 illustrated is the application of amino acid reduzate amino alcohol beta-cyclodextrin derivative in aqueous metal catalysis organic synthesis.
What embodiment 9 illustrated is the application of amino alcohol beta-cyclodextrin derivative in aqueous phase molecular recognition.
Embodiment 1:
In 250ml eggplant shaped reaction device, single for 32.23g (25.0mmol) (6-O-p-tosyl group)-beta-cyclodextrin and 3.43g (25.0mmol) L-benzene glycinol are dissolved in the anhydrous HMPA of 100mL, in N
2under atmosphere, 110 DEG C of stirring reaction 48.0h.After gained reaction mixture cool to room temperature, be slowly added drop-wise in 200mL dehydrated alcohol, leave standstill, suction filtration, recrystallization twice in water, by gained solid vacuum-drying 4.0h at 110 DEG C, obtains white solid (CD-1) 28.54g, yield 91.07%.
CD-1:m.p.＞260℃；
1HNMR(D
2O,400MHz)δ:7.39～7.17(m,7H),5.10～4.86(m,13H),4.07～3.71(m,24H),3.70～3.25(m,28H),3.21～2.93(m,5H),2.79(2H),2.66ppm(m,2H)；
13CNMR(DMSO-d
6,400MHz)δ:140.79,128.10～126.96,101.80～101.06,84.12,80.61,72.98～71.86,68.83,66.22,62.84,59.78,46.65ppm；MS(ESI)m/z:1254.4[M+H]
+,1276.5[M+Na]
+.
Embodiment 2:
In 250ml eggplant shaped reaction device, single for 32.23g (25.0mmol) (6-O-p-tosyl group)-beta-cyclodextrin and 3.78g (25.0mmol) D-phenylalaninol are dissolved in the anhydrous HMPA of 100mL, in N
2under atmosphere, 110 DEG C of stirring reaction 48.0h.After gained reaction mixture cool to room temperature, be slowly added drop-wise in 200mL dehydrated alcohol, leave standstill, suction filtration, recrystallization twice in water, by gained solid vacuum-drying 4.0h at 110 DEG C, obtains white solid (CD-2) 28.73g, yield 90.63%.
CD-2：m.p.＞265℃；
1HNMR(D
2O,400MHz)δ:7.37～7.08(m,5H),5.15～4.84(m,10H),3.95～3.72(m,15H),3.70～3.62(m,7H),3.62～3.33(m,18H),3.31～3.15(m,2H),2.92～2.68(m,3H),2.63～2.47(m,2H)ppm；MS(ESI):m/z:1268.5[M+H]
+,1290.4[M+Na]
+.
Embodiment 3:
In 250ml eggplant shaped reaction device, single for 32.23g (25.0mmol) (6-O-p-tosyl group)-beta-cyclodextrin and 3.78g (25.0mmol) L-phenylalaninol are dissolved in the anhydrous HMPA of 100mL, in N
2under atmosphere, 110 DEG C of stirring reaction 48.0h.After gained reaction mixture cool to room temperature, be slowly added drop-wise in 200mL dehydrated alcohol, leave standstill, suction filtration, recrystallization twice in water, by gained solid vacuum-drying 4.0h at 110 DEG C, obtains white solid (CD-3) 28.96g, yield 91.34%.
CD-3：m.p.＞265℃；δ:7.50～7.27(m,4H),7.21～7.06(m,2H),5.17～4.85(m,10H),3.99～3.66(m,24H),3.58～3.32(m,22H),3.31～3.03(m,3H),2.91(1H),2.80～2.46(m,3H)ppm；MS(ESI):m/z:1268.3[M+H]
+,1290.3[M+Na]
+.
Embodiment 4:
In 250ml eggplant shaped reaction device, single for 32.23g (25.0mmol) (6-O-p-tosyl group)-beta-cyclodextrin and 1.87g (25.0mmol) L-Propanolamine are dissolved in the anhydrous HMPA of 100mL, in N
2under atmosphere, 110 DEG C of stirring reaction 48.0h.After gained reaction mixture cool to room temperature, be slowly added drop-wise in 200mL dehydrated alcohol, leave standstill, suction filtration, recrystallization twice in water, by gained solid vacuum-drying 4.0h at 110 DEG C, obtains white solid (CD-4) 27.78g, yield 93.22%.
CD-4:m.p.＞250℃；
1HNMR(D
2O,400MHz)δ:5.16～4.92(m,11H),4.27～3.70(m,35H),3.67～3.29(m,23H),3.10～2.29(m,2H),2.85～2.68(m,3H),2.21(m,1H),1.00ppm(m,3H)；MS(ESI):m/z:1192.5[M+H]
+,1214.5[M+Na]
+.
Embodiment 5:
In 250ml eggplant shaped reaction device, single for 32.23g (25.0mmol) (6-O-p-tosyl group)-beta-cyclodextrin and 2.58g (25.0mmol) L-valerian ammonia alcohol are dissolved in the anhydrous HMPA of 100mL, in N
2under atmosphere, 110 DEG C of stirring reaction 48.0h.After gained reaction mixture cool to room temperature, be slowly added drop-wise in 200mL dehydrated alcohol, leave standstill, suction filtration, recrystallization twice in water, by gained solid vacuum-drying 4.0h at 110 DEG C, obtains white solid (CD-5) 27.63g, yield 90.59%.
CD-5：m.p.＞255℃；
1HNMR(D
2O,400MHz)δ:5.13～4.91(m,10H),4.34～3.93(m,14H),3.91～3.64(m,19H),3.61～3.26(m,13H),3.17～2.15(m,1H),1.83(m,1H),1.01～0.62ppm(m,3H)；MS(ESI):m/z:1220.5[M+H]
+,1242.5[M+Na]
+.
Embodiment 6:
In 250ml eggplant shaped reaction device, single for 32.23g (25.0mmol) (6-O-p-tosyl group)-beta-cyclodextrin and 2.93g (25.0mmol) L-isoleucine alcohol are dissolved in the anhydrous HMPA of 100mL, in N
2under atmosphere, 110 DEG C of stirring reaction 48.0h.After gained reaction mixture cool to room temperature, be slowly added drop-wise in 200mL dehydrated alcohol, leave standstill, suction filtration, recrystallization twice in water, by gained solid vacuum-drying 4.0h at 110 DEG C, obtains white solid (CD-6) 27.34g, yield 88.60%.
CD-6：:m.p.＞260℃；
1HNMR(D
2O,400MHz)δ:5.20～4.90(m,14H),4.12～3.74(m,26H),3.71～3.44(m,26H),3.41～3.24(m,4H),3.05～2.95(m,1H),2.88～2.44(m,3H),1.56(1H),1.31～1.03(m,2H),0.97～0.79(m,4H),0.78～0.64(m,3H)ppm；MS(ESI):m/z:1234.5[M+H]
+,1256.6[M+Na]
+.
Embodiment 7:
In 250ml eggplant shaped reaction device, single for 32.23g (25.0mmol) (6-O-p-tosyl group)-beta-cyclodextrin and 2.93g (25.0mmol) L-leucinol are dissolved in the anhydrous HMPA of 100mL, in N
2under atmosphere, 110 DEG C of stirring reaction 48.0h.After gained reaction mixture cool to room temperature, be slowly added drop-wise in 200mL dehydrated alcohol, leave standstill, suction filtration, recrystallization twice in water, by gained solid vacuum-drying 4.0h at 110 DEG C, obtains white solid (CD-7) 27.93g, yield 90.52%.
CD-7：m.p.＞260℃；
1HNMR(D
2O,400MHz)δ:5.17～5.08(m,1H),5.05～4.89(m,6H),4.05～3.89(m,2H),3.88～3.73(m,17H),3.70～3.41(m,22H),3.36～3.20(m,3H),3.14～2.99(m,2H),2.84～2.59(m,3H),1.49(1H),1.19～0.95(m,2H),0.91～0.78(m,6H)ppm；MS(ESI):m/z:1234.6[M+H]
+,1256.6[M+Na]
+.
Embodiment 8:
In 500ml round-bottomed flask, by 5mmol beta-cyclodextrin derivative (CD-1 ~ CD-7) and metal-salt 0.425g (2.5mmol) CuCl
22H
2o is dissolved in the HCOONa2H of 200ml
2in O (50.0mmol) aqueous solution, after stirred at ambient temperature 1.0h, add 1-acetonaphthone 42.55g (250mmol), after continuing stirring reaction 1.0h, reactant is placed in 0 DEG C of stirring reaction 12h, mixed solution 4 × 50ml dichloromethane extraction merges organic layer, anhydrous Na
2sO
4drying, decompression precipitation, obtain transparent liquid, HPLC analyzes (V
normal hexane: V
virahol=95:5,0.5mL/min, 254nm), yield 93%, ee%, 91% (R).
Embodiment 9:
In aqueous, the concentration (6.0 × 10 of fixing methyl phenyl ketone
-5mol/L), the concentration adding beta-cyclodextrin derivative (CD-4, CD-5, CD-6, CD-7) respectively gets 6.0 × 10
-4mol/L, after 25 DEG C of stirring vibration 24h, take beta-cyclodextrin derivative as reference, measure its ultra-violet absorption spectrum and change successively, at maximum absorption 246nm place, it is 0.6688 that methyl phenyl ketone ultra-violet absorption spectrum raises successively from 0.6645,0.6673,0.6658,0.6651, illustrate that methyl phenyl ketone uv-absorbing changes with different beta-cyclodextrin derivative, this is because different beta-cyclodextrin derivative forms the change of methyl phenyl ketone ultra-violet absorption spectrum to the molecular recognition of methyl phenyl ketone in aqueous phase.
Claims (9)
1. one kind based on amino acid reduzate amino alcohol beta-cyclodextrin derivative, its feature comprises: L-benzene glycinol modifies beta-cyclodextrin, D-phenylalaninol modifies beta-cyclodextrin, L-phenylalaninol modifies beta-cyclodextrin, L-Propanolamine modifies beta-cyclodextrin, L-valerian ammonia alcohol modifies beta-cyclodextrin, and L-isoleucine alcohol modifies beta-cyclodextrin, and L-leucinol modifies beta-cyclodextrin; Modify the hydroxyl that position is beta-cyclodextrin C-6, its structural formula is as follows:
Wherein,
2. described in claim 1 based on the preparation method of amino acid reduzate amino alcohol beta-cyclodextrin derivative; its feature comprises step: be dissolved in anhydrous polar aprotic solvent by single (6-O-p-tosyl group)-beta-cyclodextrin and amino alcohol; under nitrogen atmosphere; stirring reaction at the reaction temperatures, after gained reaction mixture cool to room temperature, is slowly added drop-wise in dehydrated alcohol; leave standstill; suction filtration, recrystallization in water, namely obtains product by the vacuum-drying of gained solid.
3. preparation method according to claim 2, is characterised in that the mol ratio of described list (6-O-p-tosyl group)-beta-cyclodextrin and amino alcohol is 1:1 ~ 1:100.
4. preparation method according to claim 2, described anhydrous polar aprotic solvent is the one in acetonitrile, hexamethyl-phosphoramide, DMF and methyl-sulphoxide.
5. preparation method according to claim 2, is characterized in that temperature of reaction is 60 ~ 150 DEG C; Reaction times is 8.0 ~ 120.0h.
6. be according to claim 1ly aqueous metal catalysis organic synthesis based on amino acid reduzate amino alcohol beta-cyclodextrin derivative, or the application in aqueous phase molecular recognition.
7. application according to claim 6, is characterized in that, the application of described beta-cyclodextrin derivative in aqueous metal catalysis aromatic ketone asymmetric reduction.
8. application according to claim 7, is characterized in that comprising the following steps: beta-cyclodextrin derivative and metal-salt are dissolved in HCOONa2H
2in the O aqueous solution, stirred at ambient temperature, then adds aromatic ketone, after reaction mixture stirring reaction, adds dichloromethane extraction and merges organic layer, anhydrous Na
2sO4 is dry, obtains transparent liquid after decompression precipitation.
9. according to the application of claim 7 or 8, it is characterized in that, described aromatic ketone is the compound with following formula:
Wherein R is selected from methyl, ethyl, propyl group, butyl, sec.-propyl, the tertiary butyl, phenyl, 1-naphthyl, 2-naphthyl, methoxyl group, hydroxyl, amino, methylamino-, chlorine or nitro.
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Cited By (2)
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| CN109824801A (en) * | 2019-02-20 | 2019-05-31 | 江南大学 | A kind of synthetic method of cyclodextrin modified DOPA amine derivative |
| CN110590973A (en) * | 2019-10-28 | 2019-12-20 | 滕州京腾鑫汇新材料科技有限公司 | Cyclodextrin derivatives and process for producing the same |
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| CN101235104A (en) * | 2007-01-31 | 2008-08-06 | 北京理工大学 | Six kinds of alpha-schiff base derived beta-cyclodextrin and use |
| CN102585040A (en) * | 2012-02-03 | 2012-07-18 | 中山大学 | Beta-cyclodextrin derivative based on annular alkamine as well as preparation method and application of beta-cyclodextrin derivative |
| CN102627704A (en) * | 2012-03-26 | 2012-08-08 | 中山大学 | Beta-cyclodextrin derivative and preparation method and application thereof |
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| CN102585040A (en) * | 2012-02-03 | 2012-07-18 | 中山大学 | Beta-cyclodextrin derivative based on annular alkamine as well as preparation method and application of beta-cyclodextrin derivative |
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Cited By (4)
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| CN109824801A (en) * | 2019-02-20 | 2019-05-31 | 江南大学 | A kind of synthetic method of cyclodextrin modified DOPA amine derivative |
| CN109824801B (en) * | 2019-02-20 | 2021-05-18 | 江南大学 | Synthesis method of cyclodextrin modified dopamine derivative |
| CN110590973A (en) * | 2019-10-28 | 2019-12-20 | 滕州京腾鑫汇新材料科技有限公司 | Cyclodextrin derivatives and process for producing the same |
| CN110590973B (en) * | 2019-10-28 | 2021-11-05 | 淮北云端文化传媒有限公司 | Cyclodextrin derivatives and process for producing the same |
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