406682-04-0

Basic information

• Product Name: cis-cyclohex-4-ene-1,2-diol
• Synonyms: cis-cyclohex-4-ene-1,2-diol
• CAS NO: 406682-04-0
• Molecular Weight: 114.144
• Mol File: 406682-04-0.mol

Chemical Properties

• CAS DataBase Reference: cis-cyclohex-4-ene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: cis-cyclohex-4-ene-1,2-diol(406682-04-0)
• EPA Substance Registry System: cis-cyclohex-4-ene-1,2-diol(406682-04-0)

Safety Data

• Hazardous Substances Data: 406682-04-0(Hazardous Substances Data)

Upstream product

• 110307-34-1 (3aRS,7aSR)-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-2-one 
• 65173-63-9 (+/-)-cis-6-acetoxy-cyclohex-3-enol 
• 4717-63-9 Cyclohex-1-en-4,5-diol-4,5-carbonat 
• 108545-30-8 cis-Cyclohex-4-en-1,2-diyldiacetat 
• 1165952-92-0 cyclohexa-1,4-diene 
• 6253-27-6 cis-1,2-epoxy-4-cyclohexene 
• 109478-38-8 (+/-)-trans-4-acetoxy-5-(toluene-4-sulfonyloxy)-cyclohexene 
• 108950-27-2 (+/-)-trans-6-(toluene-4-sulfonyloxy)-cyclohex-3-enol 
• 6253-27-6 4,5-epoxy-cyclohexene 

Downstream Products

• 108950-27-2 (+/-)-cis-6-(toluene-4-sulfonyloxy)-cyclohex-3-enol 
• 26431-17-4 cis-4,5-bis-(toluene-4-sulfonyloxy)-cyclohexene 
• 159292-67-8 (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexene 
• 108545-30-8 cis-Cyclohex-4-en-1,2-diyldiacetat 
• 215389-21-2 (1R,6S)-6-Benzyloxy-cyclohex-3-enol 
• 215389-04-1 (2S,3aS,7aR)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole 
• 220555-49-7 (4RS,5SR)-4,5-bis(triethylsilyloxy)cyclohexene 
• 220571-36-8 (4RS,5SR)-4,5-bis(tert-butyldiphenylsilyloxy)cyclohexene 
• 6261-35-4 cyclohexanetetrol-(1r,2c,4c,5c) 
• 45775-30-2 cyclohexanetetrol-(1r,2c,4t,5t) 
• 129884-37-3 cis-4,5-diaminocyclohexene 
• 502903-60-8 cis-cyclohex-4-ene-1,2-diazide 
• 623549-50-8 N-[6-(2,2,2-trichloroacetylamino)cyclohex-3-enyl]-2,2,2-trichloroacetamide 
• 623549-61-1 N-[6-(2,2,2-trifluoroacetylamino)cyclohex-3-enyl]-2,2,2-trifluoroacetamide 

Relevant articles and documents

Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols

Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.

Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis-Diol Scaffolds

The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using aminotriphenolate-based metal catalysts is reported. The key intermediates are cyclic carbonates, which are obtained in high yield and with high levels of diastereo- and chemoselectivity from the parent oxirane precursors and carbon dioxide. Deprotection of the carbonate structures affords synthetically useful cis-diol scaffolds with different ring sizes that incorporate various functional groups. This atom-efficient method allows the simple construction of diol synthons using inexpensive and accessible precursors and green metal catalysts and showcases the use of CO2 as a temporary protecting group. Protective Carbon: Aminotriphenolate complexes of FeIII and AlIII are highly efficient and selective catalysts for the conversion of functional (multi)cyclic oxiranes into the corresponding cis carbonates. Basic hydrolysis of the latter provides a series of useful cyclic cis-diol scaffolds in high yield. In this process, CO2 acts as both a temporary protecting group and an oxygen donor.

Chiral lithium amide base-mediated rearrangement of bis-protected meso-4,5-dihydroxy cyclohexene oxides: Enantioselective synthesis of (4R,5S) and (4S,5R)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone

The asymmetric synthesis of (4R,5S)- and (4S,5R)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone are described. Such bis-protected enones are useful intermediates in synthesis, and compounds with (4S,5R)-stereochemistry have previously been prepared from D-(-)-quinic acid. This paper reports the first synthesis of enones with (4R,5S)-stereochemistry. The route to the bis-protected enones involves chiral base-mediated rearrangement of meso-cyclohexene oxides to allylic alcohols followed by PDC oxidation. Two new chiral base reactions are described: rearrangement of a trans-epoxide generates an allylic alcohol of 76% ee (93% yield) whilst that of a cis-epoxide produces an allylic alcohol of 92% ee (38% yield); suggestions for the observed differences in yield and enantioselectivities are proposed.

Aminocyclohexylesters and uses thereof

Aminocyclohexylester compounds, including thioesters, are disclosed. The compounds of the present invention may be incorporated in compositions and kits. The present invention also discloses a variety of in vitro and in vivo uses for the compounds and com

Chiral base-mediated rearrangement of meso-cyclohexene oxides to allylic alcohols

Highly enantiomerically enriched allylic alcohols have been generated by rearranging single diastereomers of meso-cyclohexene oxides using a homochiral lithium amide base. PDC oxidation of each allylic alcohol product affords a different enantiomer of a synthetically useful cyclohexenone.

SYNTHESE VON BIS(NORCARA-2,4,2',4'-TETRAENYLIDEN) UEBER EINE CARBENDIMERISIERUNG

Aus 7,7-Dibrom-3,4-isopropylidenbicycloheptan-3,4-diol (VI) und Methyllithium in Ether, sowohl bei -50 deg C als auch unter Rueckflussbedingungen entsteht das Carben, das sofort dimerisiert.Aus diesem Dimeren laesst sich in wenigen Reaktionsschritt