17522-32-6

Basic information

• Product Name: (S)-dehydro-α-damascol
• CAS NO: 17522-32-6
• Molecular Weight: 192.301
• Mol File: 17522-32-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-dehydro-α-damascol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-dehydro-α-damascol(17522-32-6)
• EPA Substance Registry System: (S)-dehydro-α-damascol(17522-32-6)

Safety Data

• Hazardous Substances Data: 17522-32-6(Hazardous Substances Data)

Upstream product

• 52646-93-2 [(S)-2,6,6-trimethylcyclohex-2-enyl]methanol 
• 13395-71-6 2,4,4-trimethyl-2-cyclohexenone 
• 147753-66-0 (R)-2,4,4-trimethyl-2-cyclohexenyl 2-butynyl ether 
• 14505-74-9 (S)-2,6,6-trimethylcyclohex-2-enecarbaldehyde 
• 16466-97-0 1-propynylmagnesium bromide 
• 14505-74-9 α-cyclocitral 
• 134780-16-8 (R)-2,4,4-trimethyl-2-cyclohexen-1-ol 

Downstream Products

• 28102-24-1 (S)-α-damascol 
• 1161837-51-9 C₁₃H₁₈ 
• 127-41-3 alpha-ionone 
• 52340-45-1 4c-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one 
• 14398-36-8 (3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one 
• 1277166-78-5 C₂₀H₂₄O₂ 
• 116497-11-1 (2E)-1-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-2-en-1-one 

Relevant articles and documents

A simple and versatile re-catalyzed meyer-schuster rearrangement of propargylic alcohols to α,β-unsaturated carbonyl compounds

The development of a general catalytic procedure for the rapid and efficient 1,3-rearrangement of free secondary and tertiary propargylic alcohols to the corresponding α,β-unsaturated carbonyl compounds using available [ReOCl3(OPPh3)-(SMe2)] complex, was reported. The reaction was carried out under neutral environmental conditions with no racemization of potentially enolizable stereocenters with virtually complete E stereoselectivity. The reaction under dimethoxyethane, proceeded at the lower rate than in THF, but with reduced by-products and the yield obtained were highly significant. The reaction was reported to increase constantly at the expense of the (Z)-isomer 2b, where the double bong isomerization was attributed to a catalytic effect of the rhenium complex. The resulted new version of Meyer-Schuster rearrangement will find enormous application in organic synthesis to develop one-pot multistep reaction sequences.

APPLICATION OF BIOCHEMICAL METHODS IN ENANTIOSELECTIVE SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS

Enzymes as well as yeasts were used in enantioselective syntheses of bioregulators such as hormones and semiochemicals.Lipases and esterases were employed in achieving optical resolution, conversion of meso-compounds to optically active compounds, and macrolactonization.Lactase effected glucosidation of a phenolic hydroxy ketone without any protection of the functional groups.Yeasts provided a variety of optically active hydroxy esters and ketones, which served as versatile non-racemic chiral building blocks.