41513-32-0

Usage

Chemical Properties

WHITE TO SLIGHTLY BEIGE CRYSTALLINE POWDER

InChI:InChI=1/C6H10O2/c7-5-1-2-6(8)4-3-5/h1-2,5-8H,3-4H2/t5-,6-/m0/s1

Upstream product

• 1165952-91-9 cyclohexa-1,3-diene 
• 6705-51-7 3,4-epoxycyclohexene 
• 20117-77-5 4-(acetoxy)cyclohex-2-en-1-yl acetate 
• 6705-51-7 1,3-cyclohexadiene monoepoxide 
• 78776-44-0 trans-(±)-4-(acetoxy)cyclohex-2-en-1-yl acetate 
• 108-93-0 cyclohexanol 
• 77300-22-2 benzoic acid 4-hydroxycyclohex-2-enyl ester 

Downstream Products

• 128014-56-2 9H-β-Carboline-3-carboxylic acid (1S,4S)-4-hydroxy-cyclohex-2-enyl ester 
• 76152-75-5 trans-4-methoxycyclohex-2-ene-1-ol 
• 59415-76-8 trans-1,4-dimethoxy-2-cyclohexene 
• 2975-92-0 d,l-(1,2,3/4)-cyclohexanetetrol 
• 35541-65-2 trans-1.4-bis-phenylcarbamoyloxy-cyclohexane 
• 78776-44-0 trans-(±)-4-(acetoxy)cyclohex-2-en-1-yl acetate 
• 108-94-1 cyclohexanone 
• 1165952-91-9 cyclohexa-1,3-diene 
• 71-43-2 benzene 

Relevant academic research and scientific papers

Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles

A general method for alkali-metal-promoted reductive difunctionalization of alkenes has been developed by means of reduction-resistant alkoxy-substituted electrophiles. A series of 1,2-diboration and 1,2-dicarbofunctionalization products can be synthesize

Selective aliphatic carbon-hydrogen bond activation of protected alcohol substrates by cytochrome P450 enzymes

Protected cyclohexanol and cyclohex-2-enol substrates, containing benzyl ether and benzoate ester moieties, were designed to fit into the active site of the Tyr96Ala mutant of cytochrome P450cam. The protected cyclohexanol substrates were efficiently and selectively hydroxylated by the mutant enzyme at the trans C-H bond of C-4 on the cyclohexyl ring. The selectivity of oxidation of the benzoate ester protected cyclohexanol could be altered by making alternative amino acid substitutions in the P450cam active site. The addition of the double bond in the cyclohexyl ring of the benzoate ester protected cyclohex-2-enol has a debilitative effect on the activity of the Tyr96Ala mutant with this substrate. However, the Phe87Ala/Tyr96Phe double mutant, which introduces space at a different location in the active site than the Tyr96Ala mutant, was able to efficiently hydroxylate the C-H bonds of 1-cyclohex-2-enyl benzoate at the allylic C-4 position. Mutations at Phe87 improved the selectivity of the oxidation of 1-phenyl-1-cyclohexylethylene to trans-4-phenyl-ethenylcyclohexanol (92%) when compared to single mutants at Tyr96 of P450cam. the Partner Organisations 2014.

Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration

New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual-purpose catalysts to transform biomass-derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]-OH shift/DODH of 2-ene-1,4-diols and 2,4-diene-1,6-diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production of polymers and plasticizers. Copyright

Pd-catalyzed allylic alkylation cascade with dihydropyrans: Regioselective synthesis of furo[3,2- c ]pyrans

A regioselective palladium-catalyzed allylic alkylation cascade forms furo[3,2-c]pyrans from various cyclic β-dicarbonyl bis-nucleophiles and 3,6-dihydro-2H-pyran bis-electrophiles. The combination of allylic carbonate and anomeric siloxy leaving groups in the dihydropyran substrate allows control of the many regiochemical possibilities in this reaction. Annulation proceeds stereoconvergently to give cis-fused furopyrans from either cis- or trans-substituted starting material.

Metal-free borylative ring-opening of vinyl epoxides and aziridines

A rational approach towards the borylative ring-opening of vinylepoxides and vinylaziridines, by the in situ formed MeO-→bis(pinacolato) diboron adduct, has been developed. The enhanced nucleophilic character of the Bpin (sp2) moiety

Synthesis of syn and anti 1,4-diols by copper-catalyzed boration of allylic epoxides

Two sides of the same coin: Syn and anti 1,4-diols have been synthesized through the regio- and diastereoselective CuI-catalyzed boration of allylic epoxides (see scheme; pin=pinacolato, TES=triethylsilyl). In situ protection of the alcohol all

Synthesis of 2-ene-1,4-diols by a new cascade-opening of 1,3-diepoxides: Towards an efficient synthesis of dihydroxytaxoid derivatives

The synthesis of dihydroxytaxoid derivatives, specially 2-Ene-1,4-diols using a new cascade-opening of 1,3-diepoxides was investigated. The study prepared a framework through a cascade ring-closing dienyne metathesis (RCDEYM) reaction from Dienyne. The me

An efficient protocol for the enantioselective preparation of a key polyfunctionalized cyclohexane. New access to (R)- and (S)-4-hydroxy-2- cyclohexenone and (R)- and (S)-trans-cyclohex-2-ene-1,4-diol

(Chemical Equation Presented) Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (±)-7. A highly efficie

An efficient approach to either enantiomer of trans-cyclohex-2-ene-1,4-diol

(1S,4S)-Cyclohex-2-ene-1,4-diol has been synthesised starting from a chiral p-benzoquinone equivalent. The sequence can be equally applied to the preparation of the (1R,4R)-enantiomer of the target diol.

Synthetic applications of functionalized silyl anions: Aminosilyl anions as hydroxy anion equivalent

An (aminosilyl)lithium and the corresponding copper and magnesium reagents serve as a hydroxy anion equivalent through (1) allylic substitution, (2) addition to vinyloxirane, and (3) addition to acetylene, followed by oxidative cleavage of the silicon-carbon bonds. Highly regio- and stereoselective transformations have been achieved in all cases.