Description
1,4-benodioxan-6-carboxaldehyde is a kind of aldehyde derivative. It is a useful intermediate in organic synthesis. It can be used as the building bock of the manufacturing tetrahydroisoquinoliones and benzofuran analog (a inhibitor of cAMP-specific phosphodiesterase type IV). It can also be used as an intermediate during the manufacturing of some novel Dopamine D3 and D4 receptor antagonists. It can also be used as the initial material for the manufacturing of some novel chalcone analogues that exhibit strong anti-tumor activity and low toxic side effects.
Chemical Properties
Yellowish-beige powder and chunks
Uses
1,4-Benzodioxan-6-carboxaldehyde finds its uses as building block in the synthesis of tetrahydroisoquinolinones, in the preparation of benzofuran analog, a potential inhibitor of CAMP-specific phosphodiesterase type IV, in the synthesis of (5Z)-5-(2,3-dihydro-1,4-benzodioxan-6-ylmethylene)-1-methyl-2-thioxoimidazolidin-4-one. It was screened as a fragment for inhibitors of PDEA using enthalpy arrays and X-ray crystallography. 1,4-Benzodioxane-6-carboxaldehyde have also been used as an intermediate in the synthesis of a new class of Dopamine D3 and D4 receptor antagonists.
Uses
1,4-Benzodioxane-6-carboxaldehyde was screened as a fragment for inhibitors of PDEA using enthalpy arrays and X-ray crystallography. 1,4-Benzodioxane-6-carboxaldehyde have also been used as an interme
diate in the synthesis of a new class of Dopamine D3 and D4 receptor antagonists.
Definition
ChEBI: 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde is a heteroarenecarbaldehyde in which a formyl group is located at position 6 of 2,3-dihydro-1,4-benzodioxine. It is a heteroarenecarbaldehyde and a benzodioxine.
Synthesis
In this step, 3,4-dihydroxybenzaldehyde was used as the starting material to synthesize the intermediate 2,3-dihydro-1,4-benzodioxane-6-carbaldehyde by nucleophilic substitution reaction with 1,2-dibromoethane under alkaline conditions. The base used in this reaction was potassium hydroxide and the phase transfer catalyst was tetrabutylammonium bromide; the molar ratio of the reactants was 3,4-dihydroxybenzaldehyde:1,2-dibromoethane=1:5; the amount of sodium hydroxide was more than five times that of 3,4-dihydroxybenzaldehyde to ensure that the reaction was carried out under strong basic conditions. The reaction temperature was maintained at reflux temperature.
References
https://www.alfa.com/zh-cn/catalog/A18696/
Jiang, Ji Miao, et al. "Study on the synthesis and anti-tumor activity of novel chalcone analogues." Chemical Research & Application 22.11(2010): 1405-1408.
