28916-38-3

Usage

InChI:InChI=1/C6H8O/c1-2-3-4-5-6-7/h2,7H,1,5-6H2

Upstream product

• 75-21-8 oxirane 
• 689-97-4 3-buten-1-yne 
• 764-41-0 1,4-dichloro-2-butene 
• 310447-99-5 3,4-dichlorobut-1-ene 
• 14763-72-5 3-buten-1-ynylmagnesium bromide 
• 593-60-2 Vinyl bromide 
• 927-74-2 3-Butyn-1-ol 
• 211310-91-7 tetrahydropyranyloxy hex-5-yne-3-ene 
• 50-00-0 formaldehyd 
• 42050-66-8 1-bromopent-4-en-2-yne 

Downstream Products

• 161881-42-1 Chloro-hex-5-en-3-ynyloxy-diphenyl-silane 
• 69925-34-4 (Z)-Buttersaeure- 
• 1574-40-9 Z-pent-3-en-1-yne 

Relevant academic research and scientific papers

Palladium-Catalyzed Aminomethylation and Cyclization of Enynol to O-Heterocycle Confined 1,3-Dienes

The rational tuning of the electrophilicity of the allylpalladium intermediates enables the regioselectively intramolecular 1,2-addition of enynol in the presence of aminal. This aminomethylation and cyclization reaction via C-N bond activation and intramolecular nucleophilic addition provides a rare example for the synthesis of O-containing heterocycle-confined 1,3-dienes, which is of synthetic potential for further derivatization. The method possesses broad substrate generality as well as functional group compatibility and efficiently affords a wide range of desired products with 5-, 6-, and 8-membered O-containing heterocycles with various functional groups.

Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis

Herein we describe a protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access to the corresponding four stereoisomers of the fluorinated hydrofurans via a novel stereodivergent axial-to-central chirality transfer process.

Selective indium-mediated 1,2,4-pentatrien-3-ylation of carbonyl compounds for the efficient synthesis of vinyl allenols

(Chemical Equation Presented) A highly selective synthetic method of functionalized vinyl allenols was developed from the reactions of various carbonyl compounds with organoindium reagent in situ generated from indium and 1-bromopent-4-en-2-yne derivatives. Treatment of vinyl allenols with gold catalyst, dienophile, or indium trihalide produced the functionalized dihydrofuran, cyclohexene, or 2-halo-1,3-diene derivatives in good to excellent yields.

Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6- henicosatriene - The pheromonal component of Diacrisia obliqua

Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6- henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps.