86001-25-4

Basic information

• Product Name: rac-(S,S)-1,2-dicyclohexylethane-1,2-diol
• CAS NO: 86001-25-4
• Molecular Weight: 226.359
• Mol File: 86001-25-4.mol

Chemical Properties

• CAS DataBase Reference: rac-(S,S)-1,2-dicyclohexylethane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: rac-(S,S)-1,2-dicyclohexylethane-1,2-diol(86001-25-4)
• EPA Substance Registry System: rac-(S,S)-1,2-dicyclohexylethane-1,2-diol(86001-25-4)

Safety Data

• Hazardous Substances Data: 86001-25-4(Hazardous Substances Data)

Upstream product

• 55409-09-1 1,2-dicyclohexyl-2-hydroxy-ethanone 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 2043-61-0 cyclohexanecarbaldehyde 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 27819-71-2 2-chloro-3',4'-dimethoxybenzoin 
• 41841-04-7 2-(2-chlorophenyl)-2-hydroxy-1-(4-methoxyphenyl)ethanone 
• 931-50-0 cyclohexylmagnesium bromide 
• 144-79-6 chloromethyldiphenylsilane 
• 84072-32-2 1-[(Z)-2-(1-hydroxycyclohexyl)-1-ethenyl]-1-cyclohexanol 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 

Downstream Products

• 393166-59-1 [R-(4α,5β)]-4,5-dicyclohexyl-2-[(triphenylmethoxy)methyl]-1,3,2-dioxaborolane 

Relevant articles and documents

Facile pinacol coupling of aliphatic ketones by Brook rearrangement in the presence of samarium species

Herein we report a practical pinacol coupling reaction, in which ketones (aldehydes) react smoothly with Sm and TMSBr to afford the diol products with Sm(II) or (III) siliyl species generated in situ. This reported method affords poor yields for aromatic ketone substrates and good yields for aliphatic ketones. Therefore, it distinguishes from most reductive coupling approaches that are more effective for aromatic carbonyl compounds and provides a facile and robust approach for the pinacol coupling of aliphatic ketones. Mechanistic studies also indicated the pinacolization probably proceeded via an anionic instead of radical coupling pathway involving the Brook rearrangement in the presence of samarium (II or III) silyl species.

Pinacol couplings of a series of aldehydes and ketones with SmI2/Sm/Me3SiCl in DME

The pinacol coupling is one of the most significant methods to synthesize vic-diols. The combination of samarium diiodide (SmI2) and samarium metal successfully induces the selective pinacol couplings of not only aromatic aldehydes and ketones but also aliphatic ones in the presence of trimethylchlorosilane (Me3SiCl) in 1,2-dimethoxyethane (DME). DME is the most suitable solvent for the reduction system using SmI2 and Me3SiCl. Me3SiCl, a widely available additive, prevents the decomposition of the formed vic-diols, i.e., meso-isomers, and controls their stereochemistry. In particular, the pinacol couplings of sterically hindered aliphatic aldehydes and ketones proceed with excellent diastereoselectivities to afford dl-isomers in good yields.

Mechanistic study of half-titanocene-based reductive pinacol coupling reaction

The reductive pinacol coupling reaction of aldehydes or ketones creating a new C-C bond has been a major tool to produce 1,2-diol compounds. The reaction mechanism is known to be composed of sequential three steps (activation, coupling, and dissociation). In this work, we studied the dissociation step of half-titanocene-based catalytic systems. Cp and Cp* derivatives of the pinacolato-bridged dinuclear complex were synthesized and evaluated as possible models for intermediates from the coupling step. We monitored 1H-NMR spectra of the reaction between the metalla-pinacol intermediates and D2O. New reaction routes of the dissociation step including oxo- and pinacolato-dibridged dinuclear complexes and oxo-bridged multinuclear complexes have been suggested. Copyright

A new Yb3+-catalyzed pinacol and imine-coupling reaction

Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

Reductive self-coupling reaction of imines and aldehydes induced by strontium metal

Aromatic aldimines reacted with Sr in the presence of a catalytic amount of iodine to give self-coupling products in good yields, whereas aromatic and aliphatic aldehydes underwent a similar reaction effected by the combined use of Sr and Al(OEt)3. Copyright

Samarium diiodide-catalyzed diastereoselective pinacol couplings

(Chemical Equation Presented) A complex of samarium diiodide (Sml 2) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me2SiCl2 and Mg. Diastereoselectivity of up to 95/5 (±/meso) has been achieved for aliphatic aldehydes and up to 19/81 (±/meso) for aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions using the Sml 2/tetraglyme/Mg/Me2SiCl2 catalytic system.

Catalytic, highly enantio- and diastereoselective pinacol coupling reaction with a new tethered bis(8-quinolinolato) ligand

A new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is developed. Its chromium complex, TBOxCrCl (3 mol %), effectively catalyzes the pinacol coupling reaction of aromatic aldehydes at room temperature with high yield (up to 94%), high diast

Efficient diastereoselective pinacol coupling reaction of aliphatic and aromatic aldehydes by using newly utilized low valent titanium bromide and iodide species

Reductive coupling reaction of aromatic and aliphatic aldehydes proceeded under mild conditions to give the corresponding pinacols in moderate to high yields and DL-diastereoselectivities by using combinations of either low valent titanium(II) bromide and copper or titanium(IV) iodide and copper in a mixed solvent of dichloromethane and pivalonitrile. In the case of using titanium(IV) iodide and copper, pinacols were obtained in good to high yields with moderate to high diastereoselectivities irrespective of the number of substitutuents at α-position of aliphatic aldehydes.

Efficient diastereoselective pinacol reaction of aliphatic and aromatic aldehydes by combined use of newly utilized titanium(II) bromide and copper

Newly utilized low-valent titanium reductant, titanium(II) bromide, was conveniently prepared by treating titanium(IV) bromide with hexamethyldisilane. The pinacol reaction of aromatic and aliphatic aldehydes including primary aldehydes proceeded smoothly in dichloromethane-pivalonitrile at temperatures ranging from -23 to 0 °C by the combined use of soluble titanium(II) bromide and copper to give 1,2-diols in good to high yields with good to high dl-selectivities.