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Preparation method of monosubstituted alkynyl thiacalix [4] arene

A thia calix, mono-substituted technology is applied in the field of synthesizing thia calix[4] arene derivatives, and achieves the effects of high yield, strong selectivity and high purity

Pending Publication Date: 2022-04-01
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, strictly speaking, there is no report of a monosubstituted alkynylthiacalix[4]arene

Method used

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  • Preparation method of monosubstituted alkynyl thiacalix [4] arene
  • Preparation method of monosubstituted alkynyl thiacalix [4] arene
  • Preparation method of monosubstituted alkynyl thiacalix [4] arene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] In a 50mL round bottom flask, under nitrogen atmosphere, add 1000mg of thiacalix[4]arene, 250mg of 0.5 times cesium carbonate, 90mg of 0.5 times bromopropyne, 30mL of anhydrous acetone solvent, reflux reaction for 10 hours, and then add 0.6 Cesium bicarbonate 253 mg, 0.6 times bromopropyne 92 mg; cooled to room temperature, distilled off under reduced pressure to remove solvent acetone, added dilute hydrochloric acid to neutralize and remove excess alkali, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by column chromatography. The eluent of the column chromatography is a mixture of n-hexane and dichloromethane with a molar ratio of 3:1 to obtain 733 mg of product with a yield of 70%. It can be seen from identification that the product of this example is only a single-substituted alkynyl group Thiacalix [4] arene, its synthetic route is attached figure 2 In route 1, the product of 1 H NMR spectrum as image 3 shown.

Embodiment 2

[0032]In a 50mL round bottom flask, under a nitrogen atmosphere, add thiacalix[4]arene 1000mg, 2.1 times cesium carbonate 949mg, 1.1 times bromopropyne 182mg, 30mL anhydrous acetone solvent, reflux for 16 hours; cool to room temperature, Remove the solvent acetone by distillation under reduced pressure, add dilute hydrochloric acid to neutralize and remove excess alkali, extract with dichloromethane, dry over anhydrous sodium sulfate, and separate by column chromatography (n-hexane: dichloromethane, 1:1), the unreacted raw material is 500mg, the product is 210mg, the productive rate is 20%, and its synthetic route is attached figure 2 In route 1, it can be known through identification that the product of this scheme is only monosubstituted alkynyl thiacalix[4]arene.

Embodiment 3

[0034] In a 50mL round bottom flask, under a nitrogen atmosphere, add thiacalix[4]arene 1000mg, 1.1 times cesium carbonate 503mg, 0.5 times bromopropyne 90mg, 30mL anhydrous acetone solvent, reflux reaction for 10 hours, and then add 1 Cesium bicarbonate 446mg, 0.6 times bromopropyne 92mg; Cool to room temperature, distill off the solvent acetone under reduced pressure, add dilute hydrochloric acid to neutralize and remove excess alkali, extract with dichloromethane, dry over anhydrous sodium sulfate, and separate by column chromatography ( Normal hexane: dichloromethane, 2:1), productive rate is 41%, and its synthetic route is attached figure 2 In route 1, it can be known through identification that the product of this scheme is only monosubstituted alkynyl thiacalix[4]arene.

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Abstract

The invention discloses a preparation method of mono-substituted alkynyl thiacalix [4] arene, which comprises the following steps: feeding and blending cesium carbonate as a catalyst and halogenated alkyne as a mono-substitution reaction raw material in a thiacalix [4] arene solution for reflux reaction in an inert atmosphere, and then purifying to obtain the mono-substituted alkynyl thiacalix [4] arene, the reaction efficiency is high, the yield is high and the selectivity is strong.

Description

technical field [0001] The invention relates to the technical field of synthesizing thiacalix[4]arene derivatives, in particular to a preparation method of a monosubstituted alkynyl thiacalix[4]arene. Background technique [0002] The classic calixarene is a highly symmetrical macrocyclic compound. The four phenolic hydroxyl groups on this macrocyclic compound have the same activity, and the alkynyl group, as an indispensable functional group in the click chemical reaction, is usually introduced into the calixarene by double substitution or full substitution. On top of [4]arenes, the controlled synthesis of monosubstituted alkynylcalix[4]arene derivatives is extremely difficult. [0003] Francisco Santoyo-González et al. (J.Org.Chem.2000, 65, 4409–4414) conducted a study of regioselective classical calix[4]arene monosubstituted propargyl groups: first using a water separator device, bis(tributyltin ) oxide as initiator, and toluene is used as azeotropic solvent for removing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D341/00
CPCC07D341/00
Inventor 金宗文赵江林玄曙光
Owner SHENZHEN INST OF ADVANCED TECH
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