20325-03-5

Usage

Structure

Cyclohexan-1-ol derivative with a tert-butyl group and an ethynyl substituent attached to the cyclohexane ring

Functional groups

Hydroxyl (-OH), Ethynyl (-C≡CH), and tert-butyl (-C(CH3)3)

Applications

a. Organic synthesis
b. Pharmaceutical research
c. Building block for the synthesis of various compounds

Suitability

a. As a starting material for the synthesis of acetylenic compounds
b. Wide range of applications in medicinal chemistry and materials science

Steric hindrance

Provided by the tert-butyl group, useful for controlling the reactivity and selectivity of reactions in which the compound is involved.

InChI:InChI=1/C12H20O/c1-5-12(13)8-6-10(7-9-12)11(2,3)4/h1,10,13H,6-9H2,2-4H3

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 4301-14-8 acetylenemagnesium bromide 
• 74-86-2 acetylene 
• 136121-27-2 1-(1-Chlorovinyl)-4-t-butyl-1-cyclohexanol 
• 159763-13-0 1-<1-chloro-1-(p-tolylsulfinyl)ethyl>-4-tert-butyl-1-cyclohexanol 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 100319-42-4 4-(tert-butyl)-1-ethynylcyclohex-1-ene 
• 37881-09-7 1-acetyl-4-tert-butylcyclohex-1-ene 
• 109787-32-8 1-<<2-(4-(1,1-dimethylethyl)cyclohexylidene)ethenyl>sulfonyl>-4-methylbenzene 
• 109787-29-3 4-(1,1-dimethyl)-1-ethynylocyclohexan-1-yl 4-methylbenzenesulfinate 

Relevant academic research and scientific papers

Base-Catalyzed Borylation/B-O Elimination of Propynols and B2pin2 Delivering Tetrasubstituted Alkenylboronates

An efficient approach to tetrasubstituted alkenylboronates via a cascade borylation/B-O elimination of propynols and B2pin2 was disclosed. A series of tetrasubstituted alkenylboronates were readily furnished with this strategy in good yields, with further transformations leading to tetrasubstituted alkenes and β-diketones demonstrating the synthetic potential of the alkenylboronates constructed by this strategy as versatile intermediates in organic synthesis.

Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); A new 'metal free' life for the Rupe rearrangement

A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Br?nsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.

Catalytic dicyanative [4 + 2] cycloaddition triggered by cyanopalladation using ene-enynes and cyclic enynes with methyl acrylate

Palladium-catalyzed dicyanative [4 + 2] cycloaddition using various ene-enynes was investigated. The key species in this process is a cyanoallene intermediate that is obtained by the cyanopalladation of conjugated enynes followed by 5-exo-cyclization. To

Substituted hepta-1,6-dien-3-ones with green/fruity odours green/galbanum olfactophore model

Following an analysis of available SAR data on green/galbanum-smelling molecules, a series of new 2-substituted hepta-1,6-dien-3-ones and their analogues were prepared and their olfactory properties evaluated. The study allowed to select efficient new odourants - potential substitutes for natural galbanum oil - and to generate an olfactophore model for the green/galbanum note.

1-Chloroalkyl p-Tolyl Sulfoxides as Acetylide Anion Equivalent: A Novel Synthesis Including Asymmetric Synthesis of Propargylic Alcohols from Carbonyl Compounds

Addition of the carbanion of 1-chloroalkyl p-tolyl sulfoxide to carbonyl compounds gave the adducts, which were heated in refluxing toluene or xylene to give vinyl chlorides in high overall yield.Dehydrochlorination of the vinyl chlorides with excess n-BuLi afforded propargylic alcohols in high yields.Asymmetric synthesis of both enantiomers of the propargylic alcohols was realized using optically active 1-chloroalkyl p-tolyl sulfoxide and aldehyde.