474417-99-7

Basic information

• Product Name: 3-allyl-5,5-dimethylbicyclo[4.1.0]hept-2-en-2-yl acetate
• CAS NO: 474417-99-7
• Molecular Weight: 220.312
• Mol File: 474417-99-7.mol

Chemical Properties

• CAS DataBase Reference: 3-allyl-5,5-dimethylbicyclo[4.1.0]hept-2-en-2-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-allyl-5,5-dimethylbicyclo[4.1.0]hept-2-en-2-yl acetate(474417-99-7)
• EPA Substance Registry System: 3-allyl-5,5-dimethylbicyclo[4.1.0]hept-2-en-2-yl acetate(474417-99-7)

Safety Data

• Hazardous Substances Data: 474417-99-7(Hazardous Substances Data)

Upstream product

• 1159201-29-2 C₁₄H₂₀O₂ 
• 474417-82-8 1-allyl-1-ethynyl-3,3-dimethylpent-4-enyl acetate 

Relevant articles and documents

AuI-catalyzed cycloisomerization of 1,5-enynes bearing a propargylic acetate: Formation of unexpected bicyclo[3.1.0]hexene

The use of N-heterocyclic carbene (NHC) as a ligand in the gold(i)-catalyzed cycloisomerization of enyne results in the assembly of a new carbocyclic product. The Royal Society of Chemistry 2006.

Gold- And platinum-catalyzed cycloisomerization of enynyl esters versus alleneyl esters: An experimental and theoretical study

Experimental and theoretical studies on Au- and Pt-catalyzed cycloisomerization of a branched dienyne with an acetate group at the propargylic position are presented. The peculiar architecture of the dienyne precursor, which has both a 1,6- and a 1,5-enyne skeleton, leads, in the presence of alkynophilic gold catalysts, to mixtures of bicyclic compounds 3, 4, and 5. Formation of unprecedented bicyclo[3.1.0]hexene 5 is the main focus of this study. The effect of the ancillary ligand on the gold center was examined and found to be crucial for formation of 5. Further mechanistic studies, involving cyclization of an enantioenriched dienyne precursor, 18O-labeling experiments, and DFT calculations, allowed an unprecedented reaction pathway to be proposed. We show that bicyclo[3.1.0]hexene 5 is likely formed by a 1,3-OAc shift/allene-ene cyclization/ 1,2-OAc shift sequence, as calculated by DFT and supported by Au-catalyzed cyclization of isolated allenenyl acetate 7, which leads to improved selectivity in the formation of 5. Additionally, the possibility of OAc migration from allenyl acetates was supported by a trapping experiment with styrene that afforded the corresponding cyclopropane derivative. This unprecedented generation of a vinyl metal carbene from an allenyl ester supports a facile enynyl ester/allenenyl ester equilibrium. Further examination of the difference in reactivity between enynyl acetates and their corresponding [3,3]-rearranged allenenyl acetates toward Au- and Pt-catalyzed cycloisomerization is also presented.

Use of ionic liquids in the platinum- and gold-catalyzed cycloisomerization of enyne systems

The platinum- and gold-catalyzed cycloisomerization of enyne systems has been carried out in various ionic liquids (ILs). In some cases, better selectivities and shorter reaction times have been observed compared to conventional conditions.

PtCl2- and PtCl4-catalyzed cycloisomerization of polyunsaturated precursors

The PtCl2- and PtCl4-catalyzed cycloisomerization of polyunsaturated precursors with different O-protecting groups at the propargylic position is reported. The free hydroxy, O-(bromomethyl)dimethylsilyl, O-methyl and O-propenyl deriv

The effect of a hydroxy protecting group on the PtCl2-catalyzed cyclization of dienynes - A novel, efficient, and selective synthesis of carbocycles

The versatile ketone C can be obtained by hydrolyzing cyclooctene B, which is formed in a PtCl2-catalyzed cycloisomerization reaction from the enyne precursor A. A carbene platinum complex is invoked in the process, which also represents one of the few efficient syntheses of functionalized cyclooctanes from acyclic precursors.