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Compound with macrocyclic structure, preparation method of compound and application of compound in synthesis of capsule-shaped molecular cage

A technology of compounds and general formulas, applied in the field of organic synthesis

Active Publication Date: 2021-11-12
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the existing synthesis of molecular cages, the commonly used structural building blocks have zero-dimensional, one-dimensional or two-dimensional topological structures, which are used as vertices, edges, and planes to construct organic molecular cages. Three-dimensional structural building blocks with cavity structures to build organic molecular cages

Method used

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  • Compound with macrocyclic structure, preparation method of compound and application of compound in synthesis of capsule-shaped molecular cage
  • Compound with macrocyclic structure, preparation method of compound and application of compound in synthesis of capsule-shaped molecular cage
  • Compound with macrocyclic structure, preparation method of compound and application of compound in synthesis of capsule-shaped molecular cage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Preparation of compound 2, the synthetic route is as follows:

[0086]

[0087] Take compound 1 (2.5g, 10mmol) in a 250mL eggplant-shaped bottle preloaded with a magnet, and add solvent tetrahydrofuran (40mL). Place the eggplant-shaped bottle in an ice-water bath and stir at 0°C, weigh NaH (0.8g, 60wt%, 20mmol, 2eq.) into the bottle, and continue stirring at 0°C for 1h. Add 1-bromooctane (3.85g, 20mmol, 2eq.) to the eggplant-shaped flask, and reflux at 77°C for 8h. After the reaction was completed, it was lowered to room temperature, and H 2 O (10 mL) quenched the reaction. The product was extracted with dichloromethane (DCM), then the organic phase was washed with saturated NaCl solution, and washed with anhydrous NaCl 2 SO 4 Remove water from the organic phase. After the solvent was removed by rotary evaporation, the reaction system was separated by column chromatography (eluent: petroleum ether (PE)) to obtain compound 2 with a yield of 96%.

[0088] 1 H NM...

Embodiment 2

[0090] Preparation of compound 5, the synthetic route is as follows:

[0091]

[0092] Get compound 2 (1.8g, 5mmol) in the 250mL eggplant-shaped bottle of prepacked magnetic son, in N 2 THF (30 mL) was added into the environmental glove box to dissolve compound 2, and the reaction vial was sealed and transferred out. The eggplant-shaped flask was pre-stirred in a -78°C cold bath for 15min, n-butyllithium reagent (1.6M, 3mL, 5mmol, 1eq.) was added dropwise, and the stirring was continued at -78°C for 1.5h. Compound 4 (1.69g, 5mmol, 1eq.) was dissolved in THF (20mL), an anhydrous and oxygen-free solvent, and transferred into an eggplant-shaped flask at -78°C. After the transfer was complete, the cooling bath was warmed to -60°C and stirred for 1 hour. The reaction flask was taken out, and stirring was continued for 8 h at room temperature (25° C.). After the reaction is complete, add H 2 The reaction was quenched with O (10 mL), and the product was extracted with DCM and ...

Embodiment 3

[0095] Preparation of compound 6, the synthetic route is as follows:

[0096]

[0097] Get compound 5 (500mg, 0.8mmol) in the 250mL eggplant-shaped bottle of prepacked magnetic son, in N 2 The substrate was dissolved in toluene (50 mL) in an environmental glove box, and the vial was sealed and transferred out. Methanesulfonic acid (5 μL) was added to the reaction vial using a microsampler to obtain a dark purple solution, which was continuously stirred at 80° C. for 4 h. After the reaction, the color of the reaction system faded, and after cooling down to room temperature, triethylamine (5 mL) was added to quench the reaction. The solvent was removed by a rotary evaporator, and the reaction system was separated and purified by column chromatography (eluent PE:DCM=5:1) to obtain 154 mg of macrocyclic compound 6.

[0098] 1 H NMR (400MHz, CDCl 3 )δ7.59(d, J=8.0Hz, 6H), 7.55(s, 6H), 7.49(d, J=8.4Hz, 6H), 7.07(d, J=8.4Hz, 12H), 6.84(d, J=8.0Hz, 12H), 3.51(t, J=7.6Hz, 6H), ...

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Abstract

The invention relates to a compound shown in a general formula (I) and a preparation method thereof, wherein A is independently selected from -NR7-,-PR7-,-CH2-,-O- and -S-; R7 is independently selected from H, C1-30 alkyl and aryl; R2 is independently selected from -C[ triple bond]C-, -C=C-, -(CH2)n-(n = 0, 1, 2); R3 is independently selected from -Ar-Z, Ar is aryl or heteroaryl, and Z is -CHO or-NH2; R1 is independently selected from H, a C1-30 alkyl group, a C2-30 alkenyl group, a C2-30 alkynyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a heterocyclic group, halogen, an amino group, a sulfonic acid group, a carboxylic acid group, a C1-30 alkoxy group, an aryloxy group, a -CO-C1-30 alkyl group, a -CO-aryl group, a -COO-C1-30 alkyl group and a -COO-aryl group. The invention also relates to use of the compound of general formula (I) in preparation of a capsule-shaped molecular cage. The capsule-shaped molecular cage has a larger cavity structure and can be used in the fields of adsorption, separation, catalysis, fluorescence recognition and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a class of compounds with a macrocyclic structure, a preparation method thereof and an application for forming a capsule-shaped molecular cage. Background technique [0002] With the increasing maturity and application of supramolecular chemistry, organic molecules with large cavity structures are of great significance. Organic molecular cages are complex organic molecules with a three-dimensional topology capable of creating closed and self-contained cavities. Self-assembly is a key method for the synthesis of various organic molecular cages, through the high-yield chemical interaction and highly ordered spatial arrangement between different structural blocks to obtain the target structure. Gradually mature and controllable self-assembly synthesis also makes the structure of organic molecular cages gradually complex and the synthesis ideas more abundant. [0003] Fr...

Claims

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Application Information

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IPC IPC(8): C07D255/04C07F7/10B01J31/02C09K11/06B01J20/22B01J20/28
CPCC07D255/04C07F7/081C07F7/0812B01J31/0275C09K11/06B01J20/22B01J20/28014C09K2211/1074Y02P20/55
Inventor 丛欢刁卓毛亮亮
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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