57458-00-1

Basic information

• Product Name: 2-(1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-3,3a-dihydro-1-benzofuran-6(2H)-one
• CAS NO: 57458-00-1
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.3698
• Mol File: 57458-00-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 491°C at 760 mmHg
• Flash Point: 216.4°C
• Density: 1.27g/cm³
• Vapor Pressure: 8.71E-10mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: 2-(1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-3,3a-dihydro-1-benzofuran-6(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-3,3a-dihydro-1-benzofuran-6(2H)-one(57458-00-1)
• EPA Substance Registry System: 2-(1,3-benzodioxol-5-yl)-5-methoxy-3-methyl-3a-(prop-2-en-1-yl)-3,3a-dihydro-1-benzofuran-6(2H)-one(57458-00-1)

Safety Data

• Hazardous Substances Data: 57458-00-1(Hazardous Substances Data)

Upstream product

• 147915-99-9 2-Allyl-5-(benzyloxy)-1,4-benzoquinone 
• 4043-71-4 isosafrole 
• 1446-24-8 3-allylphenol 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 74-88-4 methyl iodide 
• 29938-06-5 2-(Benzyloxy)-1,4-benzoquinone 
• 87402-78-6 Liliflol A 

Relevant articles and documents

Burchellin and its stereoisomers: Total synthesis, structural elucidation and antiviral activity

Burchellin and its analogues are a class of neolignan natural products containing a rare core with three contiguous stereogenic centers. In previous reports, racemic burchellin was synthesized without accessing each of the enantiomers. In this paper, a concise and efficient total synthetic route to divergently access the enantiomers of burchellin and those of its 1′-epi-diastereoisomer over six steps for each is disclosed, where each of the enantiomers was obtained by preparative chiral phase HPLC purification. The key steps include the construction of a 2,3-dihydrobenzofuran moiety by two Claisen rearrangements and a one-step rearrangement/cyclization and subsequent tandem ester hydrolysis/oxy-Cope rearrangement/methylation to furnish the basic skeleton of burchellin. The structures and absolute configurations of the four stereoisomers were determined using spectroscopic data analyses and comparison of experimental and calculated electronic circular dichroism data. These stereoisomers were found to have potent antiviral effects against coxsackie virus B3, and is the first time that bioactivity has been reported for these compounds. This journal is

STEREOSELECTIVE SYNTHESES OF THREE DIFFERENT CLASSES OF NEOLIGNANS FROM THE SAME STARTING MATERIALS

Lewis Acid catalyzed reactions of 2-alkoxy-5-allyl-1,4-benzoquinones with styrenes can be manipulated to form either the burchellin or guianin neolignans, or 4-allyl-2-aryl-3-methyl-2,3-dihydrobenzofurans.