131354-45-5

Basic information

• Product Name: 1-((R)-3-Hydroxy-oct-1-ynyl)-cyclohexanol
• Synonyms: 1-((R)-3-Hydroxy-oct-1-ynyl)-cyclohexanol
• CAS NO: 131354-45-5
• Molecular Weight: 224.343
• Mol File: 131354-45-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-((R)-3-Hydroxy-oct-1-ynyl)-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((R)-3-Hydroxy-oct-1-ynyl)-cyclohexanol(131354-45-5)
• EPA Substance Registry System: 1-((R)-3-Hydroxy-oct-1-ynyl)-cyclohexanol(131354-45-5)

Safety Data

• Hazardous Substances Data: 131354-45-5(Hazardous Substances Data)

Upstream product

• 32556-70-0 (R)-1-octyn-3-ol 
• 108-94-1 cyclohexanone 

Downstream Products

• 131354-49-9 (R)-1-(3-acetoxy-1-octynyl)cyclohexanol 

Relevant articles and documents

Synthesis of enantiomerically enriched 2,5-dihydrofuran derivatives from easily available enantiomerically enriched 2-butyne-1,4-diols by stereospecific transformation

The transformation of enantiomerically enriched 1,1,4-trisubstituted 4- acyloxy-2-butyn-1-ols 3 into 2,2,5-trisubstituted 3-acyloxy-2,5-dihydrofurans 5 with complete stereospecificity was achieved by an Ag(I)-mediated rearrangement of the monoesters 3 to allenic intermediates 4, followed by Ag(I)-assisted cyclization. A stereochemical analysis revealed that the newly formed carbon-oxygen bond in 5 was formed from the back side of the cleaved carbon-oxygen bond in 3. The propargyl esters 3 were prepared by an enantioselective reduction of the corresponding alkynyl ketones 1, followed by acylation. Since 3-acyloxy-2,5-dihydrofurans 5 were easily converted to the corresponding 4,5-dihydro-3(2H)-furanones 6, this sequence was successfully applied to the synthesis of a differentiation-inducing antibiotic, (S)-(-)-ascofuranone.