95413-30-2

Upstream product

• 77832-42-9 (R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one 
• 124-63-0 methanesulfonyl chloride 
• 139107-32-7 C₉H₁₁BO₄ 
• 96189-00-3 (+/-)-4-acetoxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one 
• 90428-87-8 (S)-4-acetoxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one 
• 94412-95-0 (R)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl nitrate 

Downstream Products

• 77087-34-4 (S)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-ene-1-one 
• 77832-42-9 (R)-4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one 

Relevant academic research and scientific papers

Practical and Safe Sulfonylation of 2-Alkynyl and 2-Alkenyl Alcohols Using the Combined Bases of a Catalytic Amount of Tertiary Amine and Potassium Carbonate

Several 2-alkynyl and 2-alkenyl alcohols were effectively sulfonylated with methanesulfonyl chloride or p-toluenesulfonyl chloride using the combined bases of a catalytic amount of tertiary amine and potassium carbonate.The reaction was conducted with reliable safety and while avoiding the disposal of wasted amines.The mesylation of 2-propyn-1-ol proceeded on a large scale (more than 20 kg) without a substantial production of explosive 3-chloro-1-propyne.The choice of the catalysts was important, and sterically unhindered tertiary amines, such as trimethylamine, N,N-d imethylbenzylamine, and triethylamine, were effective.Without these catalysts the reactions were significantly retarded.The reaction was so mild that it could be applied to complex and optically active 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one, which is an important alcohol moiety of synthetic pyrethroids.

PREPARATION OF OPTICALLY ACTIVE SECONDARY ALCOHOLS BY COMBINATION OF ENZYMATIC HYDROLYSIS AND CHEMICAL TRANSFORMATION

Several kinds of optically active secondary alcohols (S)-2, which are important intermediates of bioactive compounds, were prepared from the corresponding racemic acetate (+/-)-1 in high chemical and optical yields by combination of enzymatic hydrolysis and chemical transformation.

Preparation of (4S)-4-hydroxy-3-methyl-2-(2′-propynyl)-2-cyclopentenone by combination of enzymatic hydrolysis and chemical transformation

(4S)-4-Hydroxy-3-methyl-2-(2′-propynyl)-2-cyclopentenone ((S)-2), which is an important alcohol moiety of optically active pyrethroid insecticides, was prepared from the corresponding racemic acetate ((±)-1) by the combination of enzymatic hydrolysis and chemical transformation in high chemical and optical yields.

Process for producing optically active cyclopentenolones

Optically active cyclopentenolones, which are useful as an intermediate of pyrethroid insecticides, are produced from racemic cyclopentenolones according to the following procedures; (1) asymmetric hydrolysis of racemic carboxylate esters of the cyclopentenolones, (2) nitrate- or sulfonate-esterification of the asymmetrical hydrolysis products, and (3) hydrolysis of the esterification products.