80511-85-9

Upstream product

• 1066-54-2 trimethylsilylacetylene 
• 108-94-1 cyclohexanone 
• 17962-22-0 1-((trimethylsilyl)ethynyl)cyclohexanol 
• 108-24-7 acetic anhydride 
• 75-77-4 chloro-trimethyl-silane 
• 5240-32-4 1-acetoxy-1-ethynyl cyclohexane 

Downstream Products

• 1262149-39-2 C₁₀H₁₆O₂⁽¹⁸⁾O 
• 1123-27-9 1-(1-hydroxycyclohexyl)ethan-1-one 
• 52789-73-8 acetic acid 1-acetyl-cyclohexyl ester 
• 5240-32-4 1-acetoxy-1-ethynyl cyclohexane 
• 72335-58-1 1-ethynyl-1-cyclohexyl-carboxylic acid 

Relevant academic research and scientific papers

Cobalt-catalyzed carboxylation of propargyl acetates with carbon dioxide

The cobalt-catalyzed carboxylation of propargyl acetates with CO2 (1 atm) is described. The reaction proceeds at room temperature in the presence of Mn powder as a reducing reagent. Various propargyl acetates are converted to the corresponding carboxylic acids in good to high yields.

Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B

A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.

Use of 1,8-Diazabicycloundec-7-ene in Preparation of Trimethylsilyl Enol Ethers and Trimethylsilylacetylenes

Trimethylsilyl enol ethers were prepared by using a combination of chlorotrimethylsilane and 1,8-diazabicycloundec-7-ene in good yields.Trimethylsilylation of acetylenes was also achieved with the same reagents in the presence of silver salt as catalyst.