79275-63-1

Basic information

• Product Name: dimethyl(phenyl)(3-phenylprop-1-yn-1-yl)silane
• Synonyms: dimethyl(phenyl)(3-phenylprop-1-yn-1-yl)silane
• CAS NO: 79275-63-1
• Molecular Weight: 250.415
• Mol File: 79275-63-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: dimethyl(phenyl)(3-phenylprop-1-yn-1-yl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl(phenyl)(3-phenylprop-1-yn-1-yl)silane(79275-63-1)
• EPA Substance Registry System: dimethyl(phenyl)(3-phenylprop-1-yn-1-yl)silane(79275-63-1)

Safety Data

• Hazardous Substances Data: 79275-63-1(Hazardous Substances Data)

Upstream product

• 10147-11-2 propargyl benzene 
• 768-33-2 phenyldimethylsilyl chloride 
• 673-32-5 1-Phenylprop-1-yne 
• 128084-23-1 1-[dimethyl(phenyl)silyl]-3-phenylpropane-1-one 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 102-93-2 3-phenylpropionamide 

Downstream Products

• 615-13-4 2-indanone 
• 79194-28-8 C₂₃H₃₄Si₃ 
• 79194-26-6 1-phenyldimethylsilyl-1-trimethylsilyl-3-phenylpropadiene 
• 79194-27-7 1-dimethylphenylsilyl-1,3-bis(trimethylsilyl)-3-phenylpropyne 
• 79194-25-5 1-dimethylphenylsilyl-3-trimethylsilyl-3-phenylpropyne 

Relevant articles and documents

Bifunctional Biphenyl-2-ylphosphine Ligand Enables Tandem Gold-Catalyzed Propargylation of Aldehyde and Unexpected Cycloisomerization

Despite extensive studies in gold catalysis, σ-allenylgold species have not been invoked as catalytic intermediates and their reactivities not studied. This work reports for the first time they are generated in situ and undergo nucleophilic addition to activated aldehydes in a bifunctional phosphine ligand-enabled gold catalysis. This development reveals a broad range of opportunities to achieve propargylic C-H functionalization for the first time under catalytic and mild conditions. The homopropargylic alcohols generated undergo ligand-enabled cycloisomerizations involving an unexpected silyl migration.

A synthesis of enantiomerically enriched propargyl silanes

Reduction of ethyl 3-methyl-, 3-isopropyl- and 3-n-pentyl-3-[dimethyl(phenyl)silyl]propanoates 4 with DIBAL to the aldehydes 5, enol trifluoromethanesulfonate (triflate) formation using trifluoromethanesulfonic (triflic) anhydride and 2,6-di-tert-butylpyridine, and elimination using LDA, gives the propargyl silanes 8. The esters 4 could also be prepared enantiomerically enriched (11), and the final products are the enantiomerically enriched propargyl (homochiral) silanes 14.