1,1',1''-trishydroxy triptycene and synthesis method thereof

A technique for the synthesis of trihydroxytriptytylene, which is applied to the preparation of amino compounds, chemical instruments and methods, and compounds of Group 4/14 elements of the periodic table, etc. It can solve the problem that the functionalization of triptylene skeleton is rarely realized, etc. question

Inactive Publication Date: 2015-04-22
CHONGQING UNIV
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Problems solved by technology

In addition, the functionalization of specific orientations on the triptycene backbone has rarely been achieved, for example, the modification of three α-positions in the same direction on triptycene

Method used

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  • 1,1',1''-trishydroxy triptycene and synthesis method thereof
  • 1,1',1''-trishydroxy triptycene and synthesis method thereof
  • 1,1',1''-trishydroxy triptycene and synthesis method thereof

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Embodiment Construction

[0007] The present invention will be further described below in conjunction with specific methods.

[0008] 1. Synthesis of 1,8-dialkoxyanthraquinone 2: At 0°C, metal sodium (7.47g, 324mmol, 3.0equiv.) was added in batches to hexanediol monomethyl ether (170.76mL, 2163mmol, 20.0 equiv.), after the metallic sodium disappeared, 1,8-dichloroanthraquinone (30.0 g, 108 mmol, 1.0 equiv.) was added to the above solution, and the reaction temperature was raised to 60° C. and stirred for 8 h.

[0009] Post-processing: After the reaction was completed, the reaction temperature was slowly lowered to 0° C., water (100 mL) was added and stirred for about 10 min, and then DCM (100 mL) was added to separate the reactants. The organic phase was taken with a separatory funnel, and the aqueous phase was extracted with DCM (200 mL×3). After the organic phases were combined, they were washed with saturated NaCl solution (200 mL×1), followed by anhydrous NaCl 2 SO 4 Dry and filter. The obtaine...

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Abstract

The invention provides a novel compound 1,1',1''-trishydroxy triptycene A. The product is synthesized by the following steps: (1) producing 1,8-disubstituted anthraquinone from ethylene glycol monomethyl ether, metallic sodium and 1,8-dichloroanthraquinone; (2) reducing 1,8-disubstituted anthraquinone with zinc powder to obtain 1,8-disubstituted anthracene; (3) simultaneously, reacting bromine, tert-butylamine and guaiacol to obtain 2-bromo-6-methoxyphenol and reacting 2-bromo-6-methoxyphenol, sodium hydride, trimethylchlorosilane, n-butyllithium and trifluoromethanesulfonic anhydride to obtain a dehydrobenzene precursor; and (4) finally reacting 1,8-disubstituted anthracene and the dehydrobenzene precursor to produce triptycene and carrying out deprotection reaction on the crude product triptycene and boron tribromide to obtain the product 1,1',1''-trishydroxy triptycene. The product 1,1',1''-trishydroxy triptycene synthesized by the method has unique spatial structure and has potential application values in such fields as chemical bionics, molecular recognition, organic materials, and polymers with special functions.

Description

technical field [0001] The invention proposes a new compound and its chemical synthesis method, the specific compound is 1,1',1"-trihydroxytriptycene. Background technique [0002] Triptycene is a three-dimensional molecule with a unique structure composed of three benzene rings. In the spatial structure, the three benzene rings form an angle of 120° with each other, with D 3h Symmetry, it has a unique three-dimensional rigid Y-shaped framework and three open electron-rich cavities. [0003] Due to its unique characteristics, triptycene can be widely used in chemical bionics, molecular machines, functional materials and other fields: using macro-scale entities as models, it can design and synthesize molecular machines on micro-scale; The unique spatial geometric structure can be rotated through the triple symmetry axis of the bridgehead carbon atom. It is a natural molecular rotor model, which can build molecular machine models such as molecular gears and molecular motors; ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/17C07C37/055
CPCC07C37/055C07C41/18C07C41/22C07C46/00C07C209/00C07C2602/44C07F7/0805C07C50/34C07C43/20C07C43/23C07C41/30C07C39/17C07C311/63
Inventor 李杨裴立志
Owner CHONGQING UNIV
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