1584188-05-5

Basic information

• Product Name: 4-(methoxycarbonyl)phenyl methyl fumarate
• Synonyms: 4-(methoxycarbonyl)phenyl methyl fumarate
• CAS NO: 1584188-05-5
• Molecular Weight: 264.235
• Mol File: 1584188-05-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-(methoxycarbonyl)phenyl methyl fumarate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(methoxycarbonyl)phenyl methyl fumarate(1584188-05-5)
• EPA Substance Registry System: 4-(methoxycarbonyl)phenyl methyl fumarate(1584188-05-5)

Safety Data

• Hazardous Substances Data: 1584188-05-5(Hazardous Substances Data)

Upstream product

• 2756-87-8 methyl hydrogen fumarate 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 3052-50-4 monomethyl maleate 
• 17081-97-9 methyl (E)-4-chloro-4-oxo-2-butenoate 

Relevant articles and documents

Leveraging the n→π* Interaction in Alkene Isomerization by Selective Energy Transfer Catalysis

Examples of geometric alkene isomerization in nature are often limited to the net exergonic direction (ΔG°0) comparatively under-represented. Inspired by the expansiveness of the maleate to fumarate (Z→E) isomerization in biochemistry, we investigated the inverse E→Z variant to validate nO→πC=O* interactions as a driving force for contra-thermodynamic isomerization. A general protocol involving selective energy transfer catalysis with inexpensive thioxanthone as a sensitizer (λmax=402 nm) is disclosed. Whilst in the enzymatic process nO→πC=O* interactions commonly manifest themselves in the substrate, these same interactions are shown to underpin directionality in the antipodal reaction by shortening the product alkene chromophore. The process was validated with diverse fumarate derivatives (>30 examples, up to Z:E>99:1), including the first examples of tetrasubstituted alkenes, and the involvement of nO→πC=O* interactions was confirmed by X-ray crystallography.