561067-74-1

Basic information

• Product Name: 2,4-Hexadienoic acid, 4-(hydroxymethyl)-6-(phenylmethoxy)-, methyl ester, (2E,4Z)-
• CAS NO: 561067-74-1
• Molecular Formula: C15H18O4
• Molecular Weight: 262.306
• Mol File: 561067-74-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,4-Hexadienoic acid, 4-(hydroxymethyl)-6-(phenylmethoxy)-, methyl ester, (2E,4Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Hexadienoic acid, 4-(hydroxymethyl)-6-(phenylmethoxy)-, methyl ester, (2E,4Z)-(561067-74-1)
• EPA Substance Registry System: 2,4-Hexadienoic acid, 4-(hydroxymethyl)-6-(phenylmethoxy)-, methyl ester, (2E,4Z)-(561067-74-1)

Safety Data

• Hazardous Substances Data: 561067-74-1(Hazardous Substances Data)

Upstream product

• 6213-87-2 methyl (2E)-3-bromoacrylate 

Downstream Products

• 561067-75-2 methyl 6-(benzyloxy)-4-{[2-(trimethylsilyl)ethoxy]methoxy}methyl-2E,4Z-hexadienoate 

Relevant articles and documents

Preparation of perhydroisoquinolines via the intramolecular Diels-Alder reaction of N-3,5-hexadienoyl ethyl acrylimidates: A formal synthesis of (±)-reserpine

The intramolecular Diels-Alder reaction of N-3,5-hexadienoyl ethyl acrylimidates provides an efficient method for the synthesis of cis-fused hexahydroisoquinolones. As a demonstration of the stereochemical control offered by this cycloaddition, two approaches to the construction of the DE rings of reserpine are reported. In the second entry, N-((4-(trimethylsilyl)ethoxymethoxy)methyl- 6-benzyloxy-3Z, 5E-hexadienoyl)-1-aza-2-ethoxy-1,3-butadiene (40) undergoes cycloaddition to produce as the major product (4aS*,7R*,8aS*)-7-benzyloxy-5-((2-trimethylsilyl) ethoxymethoxy)methyl-3,4,4a,7,8,8a-hexahydroisoquinol-3-one (41). Cycloadduct 41 is then stereospecifically elaborated to (4aS*,5S*,6R*,7R*,8aR*)-6-methoxy-5- methoxycarbonyl-7-(3,4,5-trimethoxy)benzoyldecahydroisoquinoline-2-carboxylic acid methyl ester (3), a key intermediate previously transformed to reserpine.