(4S)-4-Hydroxy-3-methyl-2-(2-propyn-1-yl)-2-cyclopenten-1-one

The preparation method is to esterify the racemic propargyl alcohol ketone with acetic acid to generate the acetate of the propargyl alcohol ketone, place the acetate in a reaction flask, and add lipase (either Arthrobacter or Pseudomonas lipase) , Stir at 70～80℃ for 48h under the protection of nitrogen. Under the action of lipase, R-propargyl ketone acetate is easily hydrolyzed to produce R-propargyl ketone, while S-propargyl ketone acetate is not easily hydrolyzed. Keep the acetate, add toluene as the solvent in the above reaction solution, add methanesulfonyl chloride or p-toluenesulfonyl chloride dropwise, stir for 30min, R-propargyl alcohol ketone is converted to methanesulfonate and the configuration transposition occurs, and then use Acid-catalyzed hydrolysis or hydrolysis with CaCO3 to obtain crude S-propargyl ketone as a pale yellow oil, further reduced pressure distillation to obtain S-propargyl ketone. Using this method, the racemate R, S-propargyl ketone can be completely converted into S-propargyl ketone.

The chemical name of S-propargyl alcohol ketone is S-2-methyl-3-(2-propargyl)-4-oxocyclopent-2-enol, which is the preparation of dextropropynthrin (trade name benefit Dock) important intermediates.

Molecular Weight:150.17
XLogP3:-0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:150.068079557
Monoisotopic Mass:150.068079557
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:265
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes