3328-60-7

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dihydroyangonin is used as an active pharmaceutical ingredient for its potential antibacterial and antifungal properties. It can be utilized in the development of new drugs to combat bacterial and fungal infections.
Used in Agricultural Industry:
5,6-Dihydroyangonin is used as a natural pesticide for its potential antibacterial and antifungal activities. It can be employed in the development of eco-friendly and sustainable solutions to protect crops from diseases caused by bacteria and fungi.
Used in Cosmetics Industry:
5,6-Dihydroyangonin is used as an ingredient in the cosmetics industry for its potential antibacterial and antifungal properties. It can be incorporated into skincare products to help maintain a healthy skin microbiome and prevent infections.
Used in Food Industry:
5,6-Dihydroyangonin is used as a preservative in the food industry for its potential antibacterial and antifungal activities. It can be utilized to extend the shelf life of perishable food products by inhibiting the growth of spoilage-causing microorganisms.

Upstream product

• 1092383-57-7 4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one 
• 696-62-8 para-iodoanisole 
• 1092383-58-8 (Z)-4-methoxy-6-(2-iodovinyl)-5,6-dihydropyran-2-one 
• 5720-07-0 4-methoxyphenylboronic acid 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 62378-65-8 4-Hydroxy-6-(α-trans-4-methoxystyryl)-5,6-dihydro-2-pyron 
• 77-78-1 dimethyl sulfate 
• 637-69-4 4-Methoxystyrene 
• 117081-50-2 5,6-dihydro-6-ethenyl-4-hydroxy-2H-pyran-2-one 

Downstream Products

• 500-62-9 yangonin 
• 3155-55-3 5,6-dihydro-4-methoxy-6-(p-methoxyphenethyl)-2H-pyran-2-one 
• 3155-52-0 4-methoxy-6-(p-methoxyphenethyl)-2H-pyran-2-one 

Relevant academic research and scientific papers

Sulfoxide-Chelated Ruthenium Benzylidene Catalyst: a Synthetic Study on the Utility of Olefin Metathesis

We provide an experimental summary of selected advances in olefin metathesis methodology that were reported over the past decades. A stable and universal sulfoxide-chelated ruthenium olefin metathesis catalyst [RuCl2(SIMes)(=CH?C6H4?S(O)Ph)], SIMes=1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene, was introduced and its application profile was studied in detail. A range of model substrates of natural origin was developed and successfully metathesized with variants of the reaction, such as ene–yne, cross, or ring-closing metathesis. All reported reactions were performed in non-pretreated solvents and in air to demonstrate the user-friendliness of the system. Besides the great functional group tolerance exhibited by the reported complex, its compatibility with multiple solvents was determined along with its air and moisture stability. Additionally, an interesting effect increasing the reaction efficiency was observed, if reactions were performed at temperatures around the solvent boiling point.

A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2- pyrones through double Reformatsky reaction

A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to δ-hydroxy-β-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and β-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin.

Heck-matsuda arylation as a strategy to access kavalactones isolated from polygala sabulosa, piper methysticum, and analogues

Herein, we describe the total syntheses of three bioactive pyrones isolated from Polygala sabulosa (i.e., 1, 4, and 7) and eight isolated from Piper methysticum (i.e., 8-10, 13, 15, and 18-20) using the Heck-Matsuda arylation as the key strategy. The evaluation of this methodology by employing different arenediazonium tetrafluoroborates revealed that the Heck arylation was more efficient when the olefin undergoing arylation possessed the vinyl-2-pyrone structural unit instead of the vinyl dihydro-2-pyrone moiety. The Heck-Matsuda arylation of many of the examined olefins proceeded in a practical manner with total regio- and stereocontrol.

Highly regio- and stereoselective Heck reaction of allylic esters with arenediazonium salts: Application to the synthesis of kavalactones

Image Presented A highly efficient palladium-catalyzed Heck reaction of allylic esters with arenediazonium salts is described. The reaction proceeds under mild conditions, with excellent to total regio- and stereochemical control and with retention of the traditional leaving group. Furthermore, the generality of the present methodology is illustrated by the short total synthesis of the natural kavalactones, yangonine, (±)-methysticin, and (±)-dihydromethysticin.

Towards synthesis of kavalactone derivatives

Kavalactone derivatives were synthesized using a Heck reaction of the 4-methoxy-6-vinyl-5,6-dihydropyran-2-one with aryl iodides. The Suzuki-Miyaura reaction of an aryl boronic acid and (Z)-4-methoxy-6-(2-iodovinyl)-5,6-dihydropyran-2-one has also been successfully used to produce both Z and E isomers of lactones.