Hydrogenated banded[12]arene compound and preparation method thereof

A compound and hydrogen atom technology, applied in the direction of producing hydrocarbons from oxygen-containing organic compounds, preparation of halogenated hydrocarbons, carbon compound catalysts, etc., can solve problems that need to be further studied, and achieve mild, stable reaction conditions and easy separation and purification. The effect of practicality and application prospect

Active Publication Date: 2019-10-25
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, macrocyclic compounds with new structu

Method used

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  • Hydrogenated banded[12]arene compound and preparation method thereof
  • Hydrogenated banded[12]arene compound and preparation method thereof
  • Hydrogenated banded[12]arene compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: Preparation and preparation of compound (Ia) (R in the corresponding formula (I) 1 for CH 3 ; 2 for CH 3 ; 3 for Et)

[0086] The reaction formula is as follows:

[0087]

[0088] The specific preparation method is:

[0089] Put 0.1 mmol (95.0 mg) of the mixture of the compound represented by formula (IIa) and the compound represented by formula (IIb) into a 25 mL Shrek tube, and add 5 mL of dichloroethane to dissolve. At room temperature, 0.3 mmol (55 μL) trifluoromethanesulfonic acid was slowly added along the bottle wall using a microsampler, and reacted at 40° C. for 2 h. After the reaction was completed, water was added to quench, the aqueous phase was extracted with dichloromethane, the organic phases were combined and washed with saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. Spin to dry the solvent, use prefabricated thin-layer chromatography prefabricated plate separation (coating thickness 0.9~1.1mm, d...

Embodiment 2

[0153] Embodiment 2: prepare compound Ib (R in corresponding formula (I) 1 is Ph; R 2 for H; R 3 for Et)

[0154] The reaction formula is as follows:

[0155]

[0156] Add 0.1mmol (133.3mg) of a mixture of compounds represented by formula (IVaa) and formula (IVba), 3mmol (113.5mg) sodium borohydride and 2mL absolute ethanol into a 10mL Shrek tube, and stir overnight at room temperature. After the reaction, slowly add saturated ammonium chloride solution to quench. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine and dried over anhydrous sodium sulfate. After the solvent was spin-dried, the solid was dissolved in 10 mL of dichloromethane and placed in a 25 mL Shrek bottle, and 0.2 mL of methanesulfonic acid was added to react at 0°C for 0.2 h. After the reaction was quenched with water, the aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with saturated brine...

Embodiment 3

[0190] Embodiment 3: preparation compound Ic (corresponding to R in formula (I) 1 is 3,5-dimethylphenyl; R 2 for H; R 3 for Et)

[0191] The reaction formula is as follows:

[0192]

[0193] The specific preparation method is:

[0194] Add 0.1 mmol (150.3 mg) of a mixture of the compound shown in formula (IVab) and formula (IVbb), 3 mmol (113.5 mg) sodium borohydride and 2 mL of absolute ethanol into a 10 mL Shrek tube, and stir overnight at room temperature. After the reaction, slowly add saturated ammonium chloride solution to quench. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine and dried over anhydrous sodium sulfate. After the solvent was spin-dried, the solid was dissolved in 10 mL of dichloromethane and placed in a 25 mL Shrek bottle, and 0.2 mL of methanesulfonic acid was added to react at 0°C for 0.2 h. After the reaction was quenched with water, the aqueous phase was extracted with dichlo...

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Abstract

The invention discloses a hydrogenated banded[12]arene compound and a preparation method thereof. The hydrogenated banded[12]arene compound is a compound shown in a formula (I) or a stereoisomer of the compound shown in the formula (I) (please see the specification for the formula). The preparation method includes the steps that an alkenylated calix[6]arene derivative compound shown in a formula (II) or a calix[6]arene alcohol derivative compound shown in a formula (III) (please see the specification for the formulas) reacts with acid in an organic solvent, and through cyclization reaction inmolecules, the hydrogenated banded[12]arene compound shown in the formula (I) can be obtained. Cheap and easily-available raw materials are adopted, from calix[6]reso-arene, a large quantity of calix[6]arene derivative compounds shown in the formula (II) and the formula (III) can be prepared through selective methylation, trifluorosulfonylation, transition metal catalysis coupling, Grignard reagent addition and other steps, and further through Friedel-Crafts alkylation reaction in molecules, the hydrogenated banded[12]arene compound can be conveniently prepared. Reaction conditions are relatively mild, obtained products are stable in air and easy to separate and purify, and good practicability and application prospects are achieved.

Description

technical field [0001] The present invention relates to the field of organic chemistry, in particular, the present invention relates to a hydrogenated cyclic [8] aromatic compound and a preparation method thereof. Background technique [0002] Synthetic macrocyclic compounds have the characteristics and advantages of good molecular structure designability and physical and chemical properties adjustment, and are widely used in many fields of chemistry, material science and life science. As host compounds, artificially synthesized macrocyclic compounds can recognize anions and cations and neutral guest molecules, so they can be used in separation, sensing and detection. As building blocks or templates, functionalized macrocycles are used in the construction of functional assemblies and nanomaterials and molecular machines. Macrocyclic compounds also provide unique research means and approaches for exploring chemical reaction mechanisms and supramolecular catalysis. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07C13/70C07C1/20C07C17/395C07C19/04G01N33/00G01N1/28
CPCC07C13/70C07C17/395C07C2523/44C07C2527/13C07C2531/04C07C2531/22C07C2531/24C07C2603/90G01N1/28G01N33/00C07C19/04
Inventor 王梅祥时谈浩佟硕
Owner TSINGHUA UNIV
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