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Hydrogenated cyclic [12] arene compound and preparation method thereof

A compound and hydrogen atom technology, which is applied in the production of hydrocarbons from oxygen-containing organic compounds, the preparation of halogenated hydrocarbons, and carbon compound catalysts, etc. Stable and easy separation and purification effect

Active Publication Date: 2020-09-08
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, macrocyclic compounds with new structures and functions still need to be further studied

Method used

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

Provided are a hydrogenation annule [12] aromatic compound and a preparation method therefor. The hydrogenation annule [12] aromatic compound is a stereoisomer of a represented compound or a compound as represented by formula (I), (I)

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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Patent Type & Authority Patents(China)
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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