34281-90-8

Usage

Uses

Used in Organic Synthesis:
(S,S)-(+)-1-Phenylcyclohexane-cis-1,2-diol is used as a chiral building block in organic synthesis for the preparation of complex molecules. Its unique structure and chirality allow for the creation of a wide range of compounds with specific properties and functions.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (S,S)-(+)-1-Phenylcyclohexane-cis-1,2-diol is used as a key component in the development of new drugs. Its chiral nature makes it suitable for asymmetric synthesis and catalysis, which are essential techniques in the production of enantiomerically pure drugs with desired therapeutic effects.
Used in Agrochemicals:
(S,S)-(+)-1-Phenylcyclohexane-cis-1,2-diol also finds applications in the agrochemical sector, where it is used as a chiral building block for the synthesis of biologically active compounds. These compounds can be used as pesticides, herbicides, or other agricultural chemicals with specific target selectivity and reduced environmental impact.
Used in Chemical Research and Development:
(S,S)-(+)-1-PHENYLCYCLOHEXANE-CIS-1,2-DIOL's potential applications extend to the field of chemical research and development, where it can be employed as a versatile building block for the synthesis of novel materials and molecules with unique properties. This can lead to the discovery of new drugs, advanced materials, and innovative chemical processes.

InChI:InChI=1/C12H16O2/c13-11-8-4-5-9-12(11,14)10-6-2-1-3-7-10/h1-3,6-7,11,13-14H,4-5,8-9H2/t11-,12-/m0/s1

Upstream product

• 23313-43-1 cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester 
• 99942-90-2 2-Acetoxy-1-phenyl-cyclohexanol 
• 771-98-2 1-Phenylcyclohexene 
• 4829-01-0 (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide 
• 4829-02-1 2-hydroxy-2-phenylcyclohexanone 
• 1222099-34-4 (+/-)-2-(2-tolylaminooxy)cyclohexanone 
• 100-58-3 phenylmagnesium bromide 
• 5775-23-5 1-phenylcyclohexene oxide 
• 100-47-0 benzonitrile 
• 5422-88-8 phenyl cyclopentyl ketone 
• 6740-66-5 (1-bromocyclopentyl)(phenyl)methanone 
• 19300-92-6 1-hydroxy-1-benzoylcyclopentane 
• 134780-69-1 (-)-(1S,2S)-cis-2-Acetoxy-1-phenylcyclohexanol 
• 1161819-40-4 (R)-2-(2-tolylaminooxy)cyclohexanone 

Downstream Products

• 134750-73-5 (-)-cis-2-(Methoxymethoxy)-1-phenylcyclohexanol 
• 99344-07-7 cis-2-hydroxy-2-phenylcyclohexyl methanesulfonate 
• 4912-59-8 (1R,2R)-1-phenyl-1,2-cyclohexanediol 
• 4829-02-1 (S)-(+)-2-hydroxy-2-phenylcyclohexanone 
• 134750-78-0 (-)-trans-4a,20a-Diphenyloctahydro-5,8,11,14,17,20-hexaoxabenzocyclooctadecane 
• 134875-74-4 (-)-trans-1,2-diphenylcyclohexane-1,2-diol 
• 134750-77-9 (-)-cis-4a-Phenyloctahydro-5,8,11,14,17,20-hexaoxabenzocyclooctadecane 
• 134750-75-7 2,2'-Oxydiethylenedioxybis(2-phenylcyclohexanol) 
• 134750-74-6 (+)-2,2'-Oxydiethylenedioxybis(2-phenylcyclophenylethyl methyl ether) 
• 27167-34-6 trans-1-Phenylcyclohexane-1,2-diol 
• 4829-02-1 2-hydroxy-2-phenylcyclohexanone 
• 4912-60-1 2-phenyl-2-cyclohexen-1-one 2,4-dinitrophenylhydrazone 
• 200800-47-1 (1S,2S)-2-azido-2-phenylcyclohexanol 

Relevant academic research and scientific papers

Photo-Induced Dihydroxylation of Alkenes with Diacetyl, Oxygen, and Water

Herein reported is a photo-induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane-2,3-dione), oxygen, and water dispenses with toxic reagents and intractable waste generation.

Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by N, N′-Dioxide-Metal Complexes

A highly enantioselective acyloin rearrangement of cyclic α-ketols has been developed with a chiral Al(III)-N,N′-dioxide complex as catalyst. This strategy provided an array of optically active 2-acyl-2-hydroxy cyclohexanones in moderate to good yields with high enantioselectivities. The asymmetric isomerizations of acyclic α-hydroxy aldehydes and α-iminols were achieved as well under modified conditions, affording the corresponding chiral α-hydroxy ketones and α-amino ketones in moderate results. Moreover, further transformations of product to enantioenriched diols were carried out.

Syn-dihydroxylation of alkenes using a sterically demanding cyclic diacyl peroxide

The syn-dihydroxylation of alkenes is a highly valuable reaction in organic synthesis. Cyclic acyl peroxides (CAPs) have emerged recently as promising candidates to replace the commonly employed toxic metals for this purpose. Here, we demonstrate that the structurally demanding cyclic peroxide spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione (P4) can be effectively used for the syn-dihydroxylation of alkenes. Reagent P4 also shows an improved selectivity for dihydroxylation of alkenes bearing β-hydrogens as compared to other CAPs, where both diol and allyl alcohol products compete with each other. Furthermore, the use of enantiopure P4 (labeled P4′) demonstrates the potential of P4′ for a metal-free asymmetric syn-dihydroxylation of alkenes.

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.

Bronsted Acid Mediated Direct α-Hydroxylation of Cyclic α-Branched Ketones

We report a Bronsted acid mediated direct α-hydroxylation of cyclic α-branched ketones via a tandem aminoxylation/N-O bond-cleavage process. Nitrosobenzene is used as the oxidant and subsequently promotes the liberation of the free alcohol. The desired pr

Green Organocatalytic Dihydroxylation of Alkenes

An inexpensive, green, metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2-trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.

Osmium on chelate resin: Nonvolatile catalyst for the synthesis of DIOLS from alkenes

Osmium tetraoxide (OsO4) was immobilized on a commercially available chelate resin DIAION CR11 (CR11) just by simply immersing it in a methanol solution of OsO4 at room temperature. The resulting purple solid, 5% Os/CR11, indicated no volatility, and effectively catalyzed the oxidation of various alkenes to the corresponding diols.

Novel biphenyl organocatalysts for iminium ion-catalyzed asymmetric epoxidation

Two novel chiral biphenyl iminium salts derived from L-acetonamine, containing electron-withdrawing 3,30-substituents on the biphenyl unit, have been prepared and tested as asymmetric catalysts for epoxidation of prochiral alkenes. The results are compared with those achieved using the corresponding unsubstituted system.

Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles

Reduction, please! The title reaction affords ?-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.

Synthesis and reaction of phthaloyl peroxide derivatives, potential organocatalysts for the stereospecific dihydroxylation of alkenes

To improve the synthesis and reactivity of phthaloyl peroxide derivatives a method has been developed using sodium percarbonate and phthaloyl chlorides. The reactions of the new phthaloyl peroxide derivatives with trans-stillbene as well as the improved reactivity of 3,4-dichlorophthaloyl peroxide with a variety of alkenes are reported.