953780-76-2

Basic information

• Product Name: 4-(2-bromobenzyl)-1,6-heptadiyn-4-ol
• Synonyms: 4-(2-bromobenzyl)-1,6-heptadiyn-4-ol
• CAS NO: 953780-76-2
• Molecular Weight: 277.161
• Mol File: 953780-76-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-(2-bromobenzyl)-1,6-heptadiyn-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-bromobenzyl)-1,6-heptadiyn-4-ol(953780-76-2)
• EPA Substance Registry System: 4-(2-bromobenzyl)-1,6-heptadiyn-4-ol(953780-76-2)

Safety Data

• Hazardous Substances Data: 953780-76-2(Hazardous Substances Data)

Upstream product

• 57486-69-8 methyl 2-(2-bromophenyl)acetate 
• 844857-43-8 4-(2-bromobenzyl)-1,7-bis(trimethylsilyl)-1,6-heptadiyn-4-ol 

Downstream Products

• 953780-80-8 4-(2-bromobenzyl)-1,7-diphenyl-1,6-heptadiyn-4-ol 
• 844857-46-1 (1E,6E)-4-(2-bromobenzyl)-1,7-diphenylhepta-1,6-dien-4-ol 

Relevant articles and documents

Oxygen donor-mediated equilibration of diastereomeric alkene-palladium(II) intermediates in enantioselective desymmetrizing heck cyclizations

This investigation examines the origin of enantioselection in the desymmetrization of an acyclic prochiral Heck cyclization precursor. High asymmetric induction (97-98% ee) is attributed to a temporary interaction of a Lewis basic oxygen donor with weakly Lewis acidic palladium(II). A series of control experiments combined with quantum-chemical model calculations provided sound evidence for a mechanism involving oxygen donor-mediated, rapid equilibration of diastereomeric alkene-palladium(II) complexes prior to the selectivity-determining ring-closing event, a Curtin-Hammett scenario. Our study also highlights the importance of the cationic pathway (triflate counter anions versus halido ligand) and alkene stereochemistry (E versus Z) in asymmetric Heck reactions.