1292293-96-9

Basic information

• Product Name: (2E)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one
• Synonyms: (2E)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one
• CAS NO: 1292293-96-9
• Molecular Weight: 422.521
• Mol File: 1292293-96-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2E)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one(1292293-96-9)
• EPA Substance Registry System: (2E)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one(1292293-96-9)

Safety Data

• Hazardous Substances Data: 1292293-96-9(Hazardous Substances Data)

Upstream product

• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 73569-44-5 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde 

Downstream Products

• 87080-27-1 licochalcone A 
• 151410-32-1 (2E)-1-(4-hydroxyphenyl)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}prop-2-en-1-one 

Relevant articles and documents

Concise synthesis of licochalcone a through water-accelerated [3,3]-sigmatropic rearrangement of an aryl prenyl ether

Claisen-Schmidt condensation of 4-(tetrahydropyran-2-yloxy)acetophenone with 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde gave a THP-protected chalcone ether. Removal of the THP group under mild acidic conditions gave the corresponding chalcone ether, which underwent a water-accelerated Claisen rearrangement under microwave irradiation or heating in a sealed tube in aqueous ethanol to give a good yield of licochalcone A, which has diverse biological activities; no product of deprenylation or abnormal Claisen rearrangement was formed. The abnormal Claisen rearrangement of -substituted allyl aryl ethers is known to be a problem in [3,3]-sigmatropic rearrangement reaction; this, however, was not detected in our water-accelerated system.