959273-94-0

Basic information

• Product Name: 6-[(E)-2-(4-fluorophenyl)vinyl]-4-methoxy-2H-pyran-2-one
• Synonyms: 6-[(E)-2-(4-fluorophenyl)vinyl]-4-methoxy-2H-pyran-2-one
• CAS NO: 959273-94-0
• Molecular Weight: 246.238
• Mol File: 959273-94-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-[(E)-2-(4-fluorophenyl)vinyl]-4-methoxy-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[(E)-2-(4-fluorophenyl)vinyl]-4-methoxy-2H-pyran-2-one(959273-94-0)
• EPA Substance Registry System: 6-[(E)-2-(4-fluorophenyl)vinyl]-4-methoxy-2H-pyran-2-one(959273-94-0)

Safety Data

• Hazardous Substances Data: 959273-94-0(Hazardous Substances Data)

Upstream product

• 672-89-9 4-methoxy-6-methyl-2H-pyran-2-one 
• 459-57-4 4-fluorobenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 136265-10-6 ethyl 4-fluorocinnamate 
• 1334928-11-8 4-methoxy-6-vinyl-2H-pyran-2-one 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 56070-85-0 4-methoxy-2-oxo-2H-pyran-6-carboxaldehyde 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 

Relevant articles and documents

Synthesis of novel 5,6-dehydrokawain analogs as osteogenic inducers and their action mechanisms

An imbalance between bone resorption by osteoclasts and bone formation by osteoblasts can cause bone loss and bone-related disease. In a previous search for natural products that increase osteogenic activity, we found that 5,6-dehydrokawain (1) from Alpinia zerumbet promotes osteoblastogenesis. In this study, we synthesized and evaluated series of 5,6-dehydrokawain analogs. Our structure-activity relationships revealed that alkylation of para or meta position of aromatic ring of 1 promote osteogenic activity. Among the potential analogs we synthesized, (E)-6-(4-Ethylstyryl)-4-methoxy-2H-pyran-2-one (14) and (E)-6-(4-Butylstyryl)-4-methoxy-2H-pyran-2-one (21) both significantly up-regulated Runx2 and Osterix mRNA expression at 10?μM. These osteogenic activities could be mediated by bone morphogenetic protein (BMP) and activation of p38 MAPK signaling pathways. Compounds 14 and 21 also inhibited RANKL-induced osteoclast differentiation of RAW264 cells. These results indicated that novel 5,6-dehydrokawain analogs not only increase osteogenic activity but also inhibit osteoclast differentiation, and could be potential lead compounds for the development of anti-osteoporosis agents.

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.