845464-90-6

Basic information

• Product Name: Benzenemethanol, a-(phenylethynyl)-2-(2-propenyloxy)-
• CAS NO: 845464-90-6
• Molecular Formula: C18H16O2
• Molecular Weight: 264.324
• Mol File: 845464-90-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(phenylethynyl)-2-(2-propenyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(phenylethynyl)-2-(2-propenyloxy)-(845464-90-6)
• EPA Substance Registry System: Benzenemethanol, a-(phenylethynyl)-2-(2-propenyloxy)-(845464-90-6)

Safety Data

• Hazardous Substances Data: 845464-90-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 90-02-8 salicylaldehyde 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 536-74-3 phenylacetylene 
• 89-95-2 2-methyl-benzyl alcohol 
• 6738-06-3 phenylethynylmagnesium bromide 

Downstream Products

• 1307886-80-1 1-(2-(allyloxy)phenyl)-3-phenylprop-2-yn-1-one 
• 1307886-90-3 3-allyl-2-phenyl-4H-chromen-4-one 
• 696-57-1 N-allylmorpholine 
• 109365-86-8 1-(o-hydroxyphenyl)-3-phenylpropargylic alcohol 
• 4047-76-1 8-allyl-2-phenyl-4H-chromen-4-one 

Relevant articles and documents

Steric buttressing in the Pauson-Khand reactions of benzyl enynes

The application of the intramolecular Pauson-Khand reaction of 1,n-enynes provides a convenient method for the construction of polycyclic frameworks but this process has largely been limited to the formation of 5,5- and 5,6-fused ring systems. In this report, we describe the application of the Pauson-Khand cyclization to 1,8-enynes embedded in an aromatic ring system wherein it is determined that the presence of steric buttresses in the form of t-butyl groups facilitates the cycloaddition. These reactions proceed in good yields with either thermal or oxidative activation and in the former case, the diastereoselectivities are high. An investigation of the tolerance of this cycloaddition to substitution around the 1,8-enyne demonstrates that only 2,2-disubstitution does not result in productive cyclization. Cycloadditions with hydroxyl groups at the propargylic position while leading to fused rings are compromised by side reactions leading to reduction and in some cases tautomerization. However, these byproducts are easily minimized through conversion of the hydroxyl group to the corresponding silyl ether.

Electrophilic carbon transfer in gold catalysis: Synthesis of substituted chromones

Using easily accessible aromatic alkoxy-arylalkynones, we have investigated the gold-catalyzed intramolecular addition of ethers to alkynes, to give easy access to various substituted chromones. This reaction involves the transfer of the ether substituent via a carbodemetallation process. We also noticed a competing isomerization of several starting materials for which we propose a second gold catalyzed mechanism.

Cascade reactions: Sequential homobimetallic catalysis leading to benzofurans and β,γ-unsaturated esters

The concatenation between a Pd(0)-promoted deallylation catalytic cycle and a Pd(II)-promoted heterocyclization catalytic cycle (an example of what we have named "sequential homobimetallic catalysis") has been shown to occur starting from 1-(2-allyloxyphenyl)-2-yn-1-ols 1 to afford 2-benzofuran-2- ylacetic esters 2 and β,γ-unsaturated esters in high yields under carbonylative conditions. In view of the conceptual as well as the synthetic importance of the process, the mechanistic aspects and the synthetic scope of the reaction have been investigated in detail. All the experimental evidence is in agreement with the sequential homobimetallic mechanism, and the reaction has proven to be of general synthetic applicability.