threo-2-(α-hydroxybenzyl)-3-coumaranone

Base Information

• Chemical Name: threo-2-(α-hydroxybenzyl)-3-coumaranone
• CAS No.: 14796-31-7
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.258
• Mol file: 14796-31-7.mol

Synonyms:threo-2-(α-hydroxybenzyl)-3-coumaranone

Chemical Property of threo-2-(α-hydroxybenzyl)-3-coumaranone

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of threo-2-(α-hydroxybenzyl)-3-coumaranone

There total 7 articles about threo-2-(α-hydroxybenzyl)-3-coumaranone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 43.0%

(E)-2'-hydroxychalcone epoxide (129878-47-3) → 3-oxo-2,3-dihydrobenzo[b]furan (7169-34-8) + 3-hydroxyflavone (577-85-5,66585-05-5) + rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7) + rac-trans-3-hydroxyflavanone (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7) + threo-2-(α-hydroxybenzyl)-3-coumaranone (14796-31-7) + erythro-2-(α-hydroxybenzyl)-3-coumaranone

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.0333333h; Product distribution; Mechanism; other sucstituted 2'-hydroxychalcones, other reagents: triethylamine, 4-(dimethylamino)pyridine, tetrabutylammonium hydroxide, HCl, HClO₄, other solvents: ethanol/water, water, CH₂Cl₂/water, other temperature and reaction time;

DOI:10.1021/jo960163z

Reference yield:

(E)-2'-hydroxychalcone epoxide (129878-47-3) → 3-hydroxyflavone (577-85-5,66585-05-5) + rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7) + threo-2-(α-hydroxybenzyl)-3-coumaranone (14796-31-7) + erythro-2-(α-hydroxybenzyl)-3-coumaranone

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 25h; Further byproducts given. Title compound not separated from byproducts; other reagents: triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene, tetrabutylammonium hydroxide;

DOI:10.1021/jo960163z

Reference yield:

(2-hydroxy-phenyl)-(3-phenyl-oxiranyl)-methanone (25518-22-3) → 3-oxo-2,3-dihydrobenzo[b]furan (7169-34-8) + 3-hydroxyflavone (577-85-5,66585-05-5) + rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7) + rac-trans-3-hydroxyflavanone (1621-55-2,55568-97-3,72150-59-5,91383-16-3,94233-46-2,96790-73-7) + threo-2-(α-hydroxybenzyl)-3-coumaranone (14796-31-7) + erythro-2-(α-hydroxybenzyl)-3-coumaranone

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.0333333h; Product distribution; Ambient temperature; further reagents, reaction times, solvents, temperature;

DOI:10.1016/S0040-4039(00)60674-3

upstream raw materials:

(2-hydroxy-phenyl)-(3-phenyl-oxiranyl)-methanone

2-((2S,3R)-3-Phenyl-oxiranecarbonyl)-phenol anion

(E)-2'-hydroxychalcone epoxide

Refernces

• 1、 Patonay,Toth,Adam. "A convenient and general synthesis of trans-3-hydroxyflavanones from chalcones by dimethyldioxirane epoxidation and subsequent base-catalyzed cyclization". . p. 5055 - 5058. Retrieved 2007/10/02.