3155-49-5

Basic information

• Product Name: (E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one
• CAS NO: 3155-49-5
• Molecular Weight: 260.29
• Mol File: 3155-49-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one(3155-49-5)
• EPA Substance Registry System: (E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one(3155-49-5)

Safety Data

• Hazardous Substances Data: 3155-49-5(Hazardous Substances Data)

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 
• 117081-50-2 5,6-dihydro-6-ethenyl-4-hydroxy-2H-pyran-2-one 
• 637-69-4 4-Methoxystyrene 

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 articles and documents

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.

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.

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.