125132-75-4

Basic information

• Product Name: (R,R)-(-)-1-PHENYLCYCLOHEXANE-CIS-1,2-DIOL
• Synonyms: (R,R)-(-)-1-PHENYLCYCLOHEXANE-CIS-1,2-DIOL
• CAS NO: 125132-75-4
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• Mol File: 125132-75-4.mol

Chemical Properties

• Melting Point: 121-123 °C(lit.)
• Boiling Point: 322.7°C at 760 mmHg
• Flash Point: 153.7°C
• Appearance: /
• Density: 1.179g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: (R,R)-(-)-1-PHENYLCYCLOHEXANE-CIS-1,2-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-(-)-1-PHENYLCYCLOHEXANE-CIS-1,2-DIOL(125132-75-4)
• EPA Substance Registry System: (R,R)-(-)-1-PHENYLCYCLOHEXANE-CIS-1,2-DIOL(125132-75-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 125132-75-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R,R)-(-)-1-Phenylcyclohexane-cis-1,2-diol serves as a chiral building block in organic synthesis, facilitating the creation of various pharmaceuticals and natural products. Its specific stereochemistry allows for the development of enantioselective reactions, which are crucial for producing single enantiomers of chiral compounds with desired biological activities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R,R)-(-)-1-Phenylcyclohexane-cis-1,2-diol is utilized as a key intermediate for the synthesis of chiral drugs. Its chiral nature is essential for the production of enantiomerically pure compounds, which can exhibit different pharmacological properties and reduce potential side effects associated with racemic mixtures.
Used in Chiral Recognition and Separation Processes:
(R,R)-(-)-1-Phenylcyclohexane-cis-1,2-diol is employed in the study of chiral recognition and separation processes. Its unique stereochemistry aids in understanding the interactions between chiral molecules and their environment, which is vital for the development of chiral chromatography techniques and other separation methods.
Used in the Development of New Materials and Catalysts:
In the field of chemistry, (R,R)-(-)-1-Phenylcyclohexane-cis-1,2-diol has potential applications in the development of new materials and catalysts. Its chiral properties can be leveraged to design enantioselective catalysts, which are crucial for producing enantiomerically pure compounds in various chemical reactions. Additionally, it may contribute to the creation of novel materials with specific chiral properties for use in various applications.

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-/m1/s1

Upstream product

• 4829-01-0 (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide 
• 4829-02-1 2-hydroxy-2-phenylcyclohexanone 
• 5775-23-5 1-phenylcyclohexene oxide 
• 23313-45-3 acetic acid 2-acetoxy-2-phenylcyclohexyl ester 
• 1222099-34-4 (+/-)-2-(2-tolylaminooxy)cyclohexanone 
• 100-58-3 phenylmagnesium bromide 
• 771-98-2 1-Phenylcyclohexene 
• 1161819-40-4 (R)-2-(2-tolylaminooxy)cyclohexanone 
• 4912-59-8 1-phenyl-1,2-cyclohexanediol 
• 4829-01-0 (1R,2R)-1-phenyl-1-cyclohexene oxide 
• 99942-90-2 2-Acetoxy-1-phenyl-cyclohexanol 
• 23313-43-1 cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester 

Downstream Products

• 134780-70-4 cis-1-Phenyl-2-acetoxylcyclohexanol 
• 134780-69-1 (-)-(1S,2S)-cis-2-Acetoxy-1-phenylcyclohexanol 
• 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 
• 134750-73-5 (-)-cis-2-(Methoxymethoxy)-1-phenylcyclohexanol 
• 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) 
• 98919-68-7 (1R,2S)-trans-2-phenylcyclohexanol 
• 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 

Relevant articles and documents

A novel microencapsulated osmium catalyst using cross-linked polystyrene as an efficient catalyst for asymmetric dihydroxylation of olefins in water

A novel microencapsulated osmium catalyst (PSresin-MC Os) was developed using cross-linked polystyrene. The concept of this method may go beyond that of microencapsulation. The catalyst was successfully used in asymmetric dihydroxylation in water, and it was recovered quantitatively by simple filtration and reused several times without loss of activity. The shape of the catalyst was maintained even after several uses. Moreover, no leaching of the Os component was detected.

Catalytic asymmetric dihydroxylation of C,C double bonds with osmium tetroxide using selenoxides as co-oxidants

Asymmetric dihydroxylation of olefins has been achieved in good yields and ee's using potassium osmate dihydrate (K2OsO2(OH)4, the pre-oxidant), (DHQD)2PHAL (the chiral ligand), potassium carbonate (the base) and selenoxides (the co-oxidants). Both the yield and the ee proved to be pH dependent, the highest yield and ee being found at almost the same pH values. The rate of the reaction was found to be highly dependent upon the structure of the selenoxide used. Some representative examples involving aminoxides are presented for comparison.

Filtration-free recyclable catalytic asymmetric dihydroxylation using a ligand immobilized on magnetic mesocellular mesoporous silica

A new magnetic mesocellular mesoporous silica support featuring a 3D open-pore structure has been developed for highly efficient, filtration-free recycling of chiral ligands for catalytic asymmetric dihydroxylation. Reactions using the ligand immobilized on this magnetic silica system exhibited almost the same reactivity and enantioselectivity as those obtained in the homogeneous reaction. Magnetically recovered ligand could be recycled eight times with good to excellent conservation of reaction rates and enantioselectivities.

Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2; dual role of the cinchona alkaloid ligand

(matrix presented) A novel application of the cinchona alkaloid derivative (DHQD)2PHAL in the osmium-catalyzed asymmetric dihydroxylation of olefins is presented. In a triple catalytic system using H2O2 as the terminal oxidant, the alkaloid ligand has a dual function in providing stereocontrol in the addition step and, via its N-oxidized form, acting as reoxidant for the in situ generated osmium(VI). The formation of the N-oxide is catalyzed by a biomimetic flavin.

Fluorous osmium tetraoxide (FOsO4): A recoverable and reusable catalyst for dihydroxylation of olefins

A fluorous osmium catalyst was firstly developed. It had been effectively used as recoverable and reusable catalyst in the dihydroxylation of olefins.

DRAMATIC ENANTIOSELECTIVITY CHANGE IN DIHYDROXYLATION OF OLEFINS WITH CHIRAL AMINE-OSMIUM TETROXIDE COMPLEX

A slight structural modification of a chiral diamine 1 caused a dramatic change in a sense of enantioselectivity in dihydroxylation of olefins with chiral amine-osmium tetroxide complex.

Substituent Effects on the Stereoselectivity of the Acid-Catalyzed Solvolysis of Rigid 1-Arylcyclohexene Oxides. Further Evidence for a Mechanism Implying Different Benzylic Carbocationic Species

The substituent effect on the stereoselctivity of the acid-catalyzed solvolysis of the conformationally rigid diastereoisomeric 4-tert-butyl-1-arylcyclohexene oxides 2 and 3 has been studied.As in the case of the conformationally mobile oxides 1, the syn/

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.

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

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.