41977-21-3

Upstream product

• 5410-22-0 1,2-epoxy-3-methyl-cyclohexane 
• 64-18-6 formic acid 
• 591-48-0 3-methyl-1-cyclohexene 
• 21889-89-4 rac-(1S,6S)-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one 
• 3400-78-0 2-hydroxy-3-methyl-2-cyclohexen-1-one 
• 41977-23-5 1(S)-(benzoyloxy)-2(R)-hydroxy-3(R)-methylcyclohexane 
• 41977-20-2 (2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene 
• 873-75-6 4-bromobenzenemethanol 
• 1122-91-4 4-bromo-benzaldehyde 
• 1426433-72-8 (1R,2R)-3-bromo-6-(hydroxymethyl)cyclohexa-3,5-diene-1,2-diol 
• 108-88-3 toluene 
• 21889-89-4 2,3-epoxy-3-methylcyclohexanone 
• 15806-70-9 3β-methyl-1α,2α-cyclohexanediol 
• 930-68-7 cyclohexenone 

Downstream Products

• 154461-96-8 cis-3-Methyl-trans-2-hydroxy-cyclohexanol 
• 154462-00-7 trans-3-Methyl-trans-2-hydroxy-cyclohexanol 
• 154461-99-1 (1S,2S,3R)-3-Methyl-cyclohexane-1,2-diol 
• 583-60-8 2-Methylcyclohexanone 
• 591-24-2 3-Methylcyclohexanone 
• 15806-70-9 (1RS,2RS,3SR)-3-methylcyclohexane-1,2-diol 
• 114818-64-3 (R)-3-Methyl-1-cyclopentanecarboxaldehyde 
• 98065-29-3 (3aR,4R,7aS)-4-Methyl-2,2,2-triphenyl-hexahydro-1,3-dioxa-2λ⁵-phospha-indene 
• 98065-29-3 (3aR,4S,7aS)-4-Methyl-2,2,2-triphenyl-hexahydro-1,3-dioxa-2λ⁵-phospha-indene 
• 42282-50-8 (1α,2β,3β)-3-methylcyclohexane-1,2-diyl diacetate 

Relevant academic research and scientific papers

A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols

Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used in the synthesis of ampelomins and deoxy-carbasugars

Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used as important intermediates for the preparation of ampelomins and deoxy-carbasugars was studied. These olefins were obtained in few steps from a chiral cis-diol resulting from microbial o

Enzymatic oxidation of para-substituted arenes: Access to new non-racemic chiral metabolites for synthesis

A series of para-substituted benzene derivatives were subjected to whole-cell fermentation with Escherichia coli JM109 (pDTG601), an organism expressing toluene dioxygenase (TDO). Several compounds proved to be excellent substrates for TDO, including 4-bromo-phenylacetylene, 4-bromobenzaldehyde, 4-bromobenzyl alcohol and 4-bromo-allylbenzene. Some of the first para-functionalized diene diols produced using TDO, are useful substrates for further synthetic manipulations, including their use in the potential synthesis of complex natural products.

Synthesis and reactions of enantiopure substituted benzene cis-hexahydro-1,2-diols

Enantiopure dis-dihydro-1,2-diol metabolites, obtained from toluene dioxygenase-catalysed dis-dihydroxylation of six monosubstituted benzene substrates, have been converted to their corresponding dis-hexahydro-1,2-diol derivatives by catalytic hydrogenation via their dis-tetrahydro-1,2-diol intermediates. Optimal reaction conditions for total catalytic hydrogenation of the dis-dihydro-1,2-diols have been established using six heterogeneous catalysts. The relative and absolute configurations of the resulting benzene dis-hexahydro-1,2-diol products have been unequivocally established by X-ray crystallography and NMR spectroscopy. Methods have been developed to obtain enantiopure dis-hexahydro-1,2diol diastereoisomers, to desymmetrise a meso-cishexahydro-1,2-diol and to synthesise 2-substituted cyclohexanols. The potential of these enantiopure cyclohexanols as chiral reagents was briefly evaluated through their application in the synthesis of two enantiomerically enriched phosphine oxides from the corresponding racemic phosphine precursors.

The Regiochemistry and Stereochemistry of the Hydroboration of Allylsilanes

The hydroboration of a wide range of allylsilanes 3 and 5-21 is found to be generally regioselective for attachment of the boron to C-3 and hydrogen to C-2 of the allyl unit, and to be generally stereoselective in the sense 1, with attachment of the boron

The Use of Bismuth(III) Acetate in 'Wet' and 'Dry' Prevost Reactions

cis-Diol and trans-diol derivatives can be prepared from alkenes by reaction with iodine and bismuth(III) acetate in 'wet' and 'dry' acetic acid, respectively.Reactions using lesser amounts of bismuth(III) acetate under 'dry' conditions give iodo acetates and under 'wet' conditions a mixture of iodohydrins and iodo ethers.Comparison of these reactions with those promoted by silver, copper, mercury and thallium salts is included.

Saturated analogues of poison ivy allergens. Synthesis of trans,trans- and cis,trans-3-alkyl-1,2-cyclohexanediols and sensitizing properties in allergic contact dermatitis

Saturated analogues of poison ivy and oak allergens (3-alkylcatechols), i.e. trans,trans-3-alkyl-1,2-cyclohexanediols (alkyl = CH3, n-C5H11, n-C10H21, n-C15H31), have been prepared and used to sensitize guinea pigs. Only long-chain derivatives (carbon chain length > C10) are contact sensitizers. The sensitized animals cross-react to PDC (i.e. pentadecylcatechol, one of the allergens of poison ivy), but the converse is not true (PDC-sensitized animals do not react to cyclohexanediols). cis,trans-3-n-Pentadecyl-1,2-cyclohexanediol has also been synthesized and shown to be a sensitizer. There is not cross-reaction between trans,trans- and cis,trans-3-n-pentadecylcyclohexanediols, excluding a common skin metabolite.

Reactions of Diethoxytriphenylphosphorane with Diastereoisomeric 3-Methylcyclohexane-1,2-diols. Control of Regioselectivity by Methyl Substitution during Cyclodehydration and Rearrangement of 1,2-Diols

The diastereoisomeric 3-methylcyclohexane-trans-1,2-diols undergo cyclodehydration with diethoxytriphenylphosphorane (DTPP) to afford the cis- and trans-3-methylcyclohexene oxides.The ratio of cis and trans epoxides is best explained by assuming preferential phosphoranylation of the C1 hydroxyl group followed by " 3-exo-tet " alkoxide displacement of triphenylphosphine oxide.The diastereoisomers of 3-methylcyclohexane-cis-1,2-diol afford stable ? -dioxyphosphoranes when allowed to react with DTPP.These 1,3,2-dioxaphosphoranes were subjected to flash thermolysis ( 300 deg C ) conditions and afforded the isomeric 2- and 3-methylcyclohexanones via a 1,2-hydride shift.

CYCLOHEXANE ANALOGS OF POISON IVY AND POISON OAK DERIVATIVES. A TOTALLY STEREOSELECTIVE SYNTHESIS OF TRANS,TRANS-3-ALKYL-1,2-CYCLOHEXANEDIOLS.

Pure trans,trans-3-methyl-, 3-n-pentyl-, 3-n-decyl- and 3-n-pentadecyl-1,2-cyclohexanediols have been prepared in two steps, in 55-70percent overall yields from 2-cyclohexenone.