1422253-47-1

Basic information

• Product Name: (Z)-4-bromomethylene-ε-caprolactone
• CAS NO: 1422253-47-1
• Molecular Weight: 205.051
• Mol File: 1422253-47-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-4-bromomethylene-ε-caprolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-bromomethylene-ε-caprolactone(1422253-47-1)
• EPA Substance Registry System: (Z)-4-bromomethylene-ε-caprolactone(1422253-47-1)

Safety Data

• Hazardous Substances Data: 1422253-47-1(Hazardous Substances Data)

Upstream product

• 1407169-65-6 4-(bromomethylidene)cyclohexanone 

Relevant articles and documents

A new type of stereoselectivity in Baeyer-Villiger reactions: Access to E- and Z-olefins

A new concept for accessing configurationally defined trisubstituted olefins has been developed. Starting from a common ketone precursor of the type 4-ethylidenecyclohexanone, Baeyer-Villiger monooxygenases are employed as catalysts in diastereoselective Baeyer-Villiger reactions leading to the corresponding E- or Z-configurated lactones. Wild-type cyclohexanone monooxygenase (CHMO) as catalyst delivers the E-isomers and a directed evolution mutant the opposite Z-isomers. Subsequent transition metal-catalyzed chemical transformations of a key product containing a vinyl bromide moiety provide a variety of different trisubstituted E- or Z-olefins. A model based on QM/MM sheds light on the origin of this unusual type of diastereoselectivity. In contrast to this biocatalytic approach, traditional Baeyer-Villiger reagents such as m-CPBA fail to show any selectivity, 1:1 mixtures of E- and Z-olefins being formed. Copyright