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Macromolecule immobilized cinchonine alkaloid ligand, synthesis method and use thereof

A synthetic method and polymer technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve high import costs, low enantioselectivity, and long reactions Time and other issues, to achieve the effect of not reducing activity and selectivity, high yield and selectivity, and low price

Inactive Publication Date: 2004-08-25
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some of the above studies have achieved good results, but the immobilization materials used are difficult to obtain in China, and the import cost is very high
Moreover, since most are heterogeneous reactions
Therefore, longer reaction times are required, and the yields are usually not high, and the enantioselectivity is also low

Method used

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  • Macromolecule immobilized cinchonine alkaloid ligand, synthesis method and use thereof
  • Macromolecule immobilized cinchonine alkaloid ligand, synthesis method and use thereof
  • Macromolecule immobilized cinchonine alkaloid ligand, synthesis method and use thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of 2:

[0032] Method a: Add o-phthalic anhydride (37 grams, 0.25 mol) into a 1-liter reaction flask, add ethanol to partially dissolve the solid, then slowly add 85% hydrazine hydrate (13-15 g) dropwise, after the dropwise addition, react The system was refluxed for 4-7 hours, cooled to room temperature, filtered, and the obtained solid was washed with hot ethanol for 3-5 times, and then washed with diethyl ether for 3-4 times to obtain a white solid, which was dried and the yield was 95%.

[0033] Method b. Add phthalic anhydride (91 grams), hydrazine sulfate (80 grams), sodium acetate (10 grams), 10% glacial acetic acid (1800 milliliters) in 2 liters of reaction flasks, this mixture is stirred Heat to 80-100°C, reflux for 5-7 hours, and let stand to cool. The reaction mixture was filtered, washed with 500-1000 ml of 1% HOAc, then washed with 500-1000 ml of distilled water, 500 ml of 95% ethanol, 500 ml of anhydrous acetic acid, and 500 ml of anhydrous ethe...

Embodiment 2

[0037] Synthesis of 3:

[0038] In a 1 liter dry reaction flask, add PCl under nitrogen protection 5 (218 grams), 2 (81.0) grams, then slowly raise the temperature to 120-140 ° C, keep this temperature constant, all the solids will melt within 3-4 hours, stir for another 3 hours, and then evaporate the liquid under reduced pressure to obtain a solid the remains. The residue was dissolved by adding about 500-700 ml of dichloromethane, filtered to remove insoluble matter, added 50-100 g of basic alumina to the filtrate, stirred for 1-3 h, then filtered and dried to obtain a crude product, which was weighed in tetrahydrofuran Crystallized to obtain 1,4-dichloroazyridine with a yield of 60%.

[0039] EI-MS (m / z, %) M+198;

[0040] 1 H (300Hz, CDCl3 ): δ8.10(d, 2H), 8.45(d, 2H).

Embodiment 3

[0042] Synthesis:

[0043] Weigh 10g of quinine, add it to a 500ml flask, add about 250ml of absolute ethanol, 1.5-2.0g of 10% Pd / C, hydrogenate at normal pressure for 48h, filter to remove Pd / C, and concentrate the filtrate to obtain hydrogenated quinine . Yield 100%.

[0044] EI-MS (m / z, %) M+326;

[0045] 1 H (300Hz, CDCl 3 ): δ8.5(d, 1H), 8.0(d, 1H), 7.5(d, 1H), 7.0-7.2(m, 2H), 5.5(d, 1H), 3.9(s, 3H), 2.2- 2.4 (m, 4H), 1.2-1.9 (m, 12H).

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Abstract

The present invention relates to homogeneous macromolecular immobilized dicinchonine alkaloid ligands. Said invention provids their structur formulas, and said ligand are made up by utilizing chemical bond mode to connect the chiral cinchonine ligand onto the polyethylene glycol. Said ligand can be used as catalyst for olefine asymmetric reaction, olefine hydroxyamination reaction and dihydroxylation reaction, and the yield and selectivity are high.

Description

technical field [0001] The invention relates to a class of polymer immobilized cinchonine alkaloid ligands, a synthesis method and an application thereof. Background technique [0002] The cis-dihydroxylation reaction (AD) of alkenes has been reported a long time ago, and the oxidizing agents include osmium tetroxide and potassium permanganate, but the amount of oxidizing agents is stoichiometric. In 1992, Sharpless found that cinchonine alkaloids could be used as chiral inducing ligands to realize the asymmetric dihydroxylation of alkenes in a catalytic amount (K.B.Sharpless.J.Org.Chem.1992, 57, 2768-2771). Since then, many groups have carried out studies on the cis-dihydroxylation (AD) of alkenes and achieved good results, which makes the dihydroxylation reaction now a very useful one in the synthesis of natural products, pharmaceuticals, and fine chemicals. synthetic method. In 1996, Sharpless successfully applied the dihydroxylation catalytic system to realize the asym...

Claims

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Application Information

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IPC IPC(8): B01J31/06C07D453/00C08G65/00
Inventor 林国强刘汉泉杨细文
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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