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Calix (4) arene containing coumarin structure, as well as synthesis method and use thereof

A synthesis method and coumarin technology, applied in the new technology and application field of calix[4]arene synthesis, achieving the effects of high yield, mild reaction conditions and simple operation

Inactive Publication Date: 2014-04-23
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Unfortunately, there is no literature report on the synthesis of calix[4]arenes with coumarin structure

Method used

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  • Calix (4) arene containing coumarin structure, as well as synthesis method and use thereof
  • Calix (4) arene containing coumarin structure, as well as synthesis method and use thereof

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Embodiment Construction

[0018] 1. Preparation process:

[0019] 1. Preparation of 2,8,14,20-tetrapropyl-5,11,17,23-tetraformyl-resorcinol calix[4]:

[0020] Add 30mL trifluoroacetic acid (TFA) in 250mL round bottom flask, add 10mmol 2,8,14,20-tetrapropyl-resorcinol calix [4] and 40mmol hexamethylenetetramine ( HMTA) mixture, heated to 85°C for 24h, then added 20mL of concentrated hydrochloric acid with a concentration of 1g / ml, and the mixture continued to react at 105°C for about 24h, and a large amount of yellow solid appeared in the system at this time. Suction filtration and recrystallization with methanol gave 2,8,14,20-tetrapropyl-5,11,17,23-tetraformyl-resorcinol calix[4] as a yellow solid with a yield of 65%.

[0021] Product identification 2,8,14,20-tetrapropyl-5,11,17,23-tetraformyl-resorcinol calix[4], yield: 65%, melting point: 294-296°C.

[0022] IR(KBr,cm -1 ): 3358(m), 2957(m), 2868(m), 1636(vs), 1463(s), 1379(m), 1241(m).;

[0023] 1 H-NMR (600MHz, CDCl 3 ):δ ppm ,0.9...

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Abstract

The invention discloses calix (4) arene containing a coumarin structure, as well as a synthesis method and a use thereof and relates to the technical field of chemical synthesis processes. The synthesis method comprises the following steps: firstly mixing 2, 8, 14, 20-tetrapropyl-5, 11, 17, 23-tetraformyl-resorcinol calix (4), diethyl malonate, piperidine, glacial acetic acid and ethanol, then heating to 75-80 DEG C, performing heat preservation reaction till the end of reaction, then mixing a mixture after reaction with a saturated saline solution, filtering out a precipitate, taking the precipitate and recrystallizing with methanol to obtain the high-purity calix (4) arene containing the coumarin structure. The process disclosed by the invention has the advantages of mild reaction conditions, simplicity in operation, capability of constructing four coumarin rings on a mother nucleus of the calix (4) arene by one-step reaction in a one pot and relatively high yield. The calix (4) arene containing the coumarin structure, which is synthesized by the method provided by the invention, has good phase transfer catalytic action.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis technology, in particular to a new synthesis technology and application of a class of calix[4]arenes. Background technique [0002] Studies have shown that calix[4]arenes have properties such as phase transfer catalysis and ion recognition. Therefore, current calix[4]arenes are mostly used in phase transfer catalysis and ion recognition. [0003] Coumarin is a kind of organic compound with good pharmacological activity that exists widely in nature, and its core is an aromatic conjugated oxygen heterocycle. Studies have shown that coumarin can not only be used as a spice, but also has photosensitivity, anti Viral, antibacterial and other important drug activity. However, because of its special conjugated structure, the coumarin molecule has a sheet-like molecular structure, which has poor water solubility, so the drug activity of coumarin drugs cannot be maximized due to poor biological...

Claims

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Application Information

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IPC IPC(8): C07D493/22B01J31/02C07C27/02C07C53/10C07C31/08
CPCB01J31/0209C07C29/095C07C51/412C07D493/22C07C53/10C07C31/08
Inventor 景崤壁丁兆兵沈明
Owner YANGZHOU UNIV
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