5686-96-4

Basic information

• Product Name: Cyclohexanol,1-(3-hydroxy-1-propynyl)-
• CAS NO: 5686-96-4
• Molecular Weight: 154.209
• Mol File: 5686-96-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Cyclohexanol,1-(3-hydroxy-1-propynyl)- (CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol,1-(3-hydroxy-1-propynyl)- (5686-96-4)
• EPA Substance Registry System: Cyclohexanol,1-(3-hydroxy-1-propynyl)- (5686-96-4)

Safety Data

• Hazardous Substances Data: 5686-96-4(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 107-19-7 propargyl alcohol 
• 925-90-6 ethylmagnesium bromide 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 51480-24-1 tetrahydropyranyloxypropargylmagnesium bromide 
• 21368-88-7 1-<1-Cyclohexylbutin-(2)-yl-ol-(1)-(4)-oxy>-1-butoxyethan 
• 50-00-0 formaldehyd 
• 39751-08-1 1-<3-<(tetrahydropyran-2-yl)oxy>-1-propynyl>cyclohexanol 

Downstream Products

• 6963-45-7 1-(3-hydroxypropyl)-cyclohexanol 
• 102591-21-9 3-(4-nitro-benzoyloxy)-1-[1-(4-nitro-benzoyloxy)-cyclohexyl]-propyne 
• 54339-96-7 1-(3-benzoyloxy-prop-1-ynyl)-cyclohexanol 
• 101268-65-9 2,3-diacetoxy-1-cyclohex-1-enyl-propene 
• 946090-05-7 C₁₄H₂₂O₄ 
• 59906-45-5 1-(1-Hydroxy-allyl)-cyclohexanol 
• 22516-18-3 3-(cyclohex-1-en-1-yl)propan-1-ol 
• 176-91-0 1-oxaspiro<4,5>decane 
• 192136-97-3 3-p-toluenesulfonyl-4-vinylidene-1-oxa-3-azaspiro[4.5]decan-2-one 
• 674368-22-0 1-[(E)-3-methoxycarbonyloxy-1-propenyl]cyclohexanol 
• 87071-03-2 (E)-1-(3-hydroxyprop-1-en-1-yl)cyclohexan-1-ol 

Relevant articles and documents

Fully substituted pyranones via quasi-heterogeneous genuinely ligand-free migita-stille coupling of iodoacrylates

Migita-Stille coupling of (Z)-?2-iodoacrylates with (E)-?±-stannyl allylic alcohols to furnish 5-alkylidene-4-substituted-5,6-dihydro-2H-pyran-2-ones is efficiently catalyzed by 2% Pd black in DMF, while Pd(PPh3)4 is inactive. Heterogeneous Pd released in solution is most likely responsible for the catalysis. The reaction is applicable to other substrates, without having to resort to ligands, additives, and/or solid support for Pd. The resulting pyranones can be rearranged to fully functionalized pyranones in another single step.

Synthesis of cyclic N-tosyliminocarbonates by Lewis acid catalyzed allylic substitution of trichloroacetimidates

Allylic trichloroacetimidates bearing a δ-N-tosylcarbamoyloxy group were prepared in two steps from the corresponding diols, and their Bronsted and Lewis acid catalyzed cyclization reactions were investigated. It was found that N-tosylcarbamates derived from secondary and tertiary alcohols bearing alkyl substituents undergo a chemoselective allylic alkylation to give N-tosyliminocarbonates in good isolated yields. In turn, aryl-substituted substrates tend to give oxazolines by abstraction of the carbamate functionality. The cyclization of N-tosylcarbamates derived from secondary alcohols preferentially give trans-iminocarbonates. However, the trans selectivity varied and depended on the substitution pattern, configuration of the substrate, and the catalyst. A high trans selectivity could be achieved from (E) substrates by using TMSOTf as the catalyst. The synthetic utility of iminocarbonates was demonstrated by transforming them into 1,2-diols and cyclic carbonates as well as into N-tosyloxazolidinones by a halide ion-induced rearrangement. Copyright

Synthesis of five- and six-membered dihalogenated heterocyclic compounds by electrophile-triggered cyclization

Highly substituted dihalogenated dihydrofurans, dihydropyrroles, and dihydro-2H-pyrans bearing alkyl, vinyl, aryl, and heteroaryl moieties can be prepared in good to excellent yields (up to 99%) by allowing 1,4-butyne-diol, 4-aminobut-2-yn-1-ol, and pent-2-yne-1,5-diol derivatives to react with different electrophiles (I2, IBr, and ICl) at room temperature. Both halogen atoms generated from electrophiles were used effectively. The resulting halides can be further exploited by using palladium-catalyzed coupling reactions. The presence of trace amount of water is essential for this electrophilic cyclization.