30282-14-5

Usage

Uses

Used in Chemical Synthesis:
2-HYDROXYCYCLOHEXANONE DIMER is used as a reactant for the synthesis of substrates for tin tetrachloride mediated fragmentation to produce ynones and ynoates. This application is significant in the creation of various chemical compounds and materials.
Used in Tandem Oxidation Coupling Reactions:
In the field of chemical synthesis, 2-HYDROXYCYCLOHEXANONE DIMER is also utilized as a reactant in tandem oxidation coupling reactions with diamines. This process contributes to the formation of complex molecular structures.
Used in Asymmetric Allylic Alkylation:
2-HYDROXYCYCLOHEXANONE DIMER is employed as a reactant in asymmetric allylic alkylation of enolates, a reaction that plays a crucial role in the synthesis of enantiomerically pure compounds.
Used in Formate Reduction of Allylic Carbonates:
In the production of polypropionate systems, 2-HYDROXYCYCLOHEXANONE DIMER is used as a reactant in the formate reduction of allylic carbonates, which is an essential step in the synthesis of various organic compounds.
Overall, 2-HYDROXYCYCLOHEXANONE DIMER is a versatile reactant with applications in different areas of chemical synthesis, contributing to the development of new compounds and materials.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 130, 1986 DOI: 10.1021/jo00352a002Synthetic Communications, 25, p. 3141, 1995 DOI: 10.1080/00397919508015463Tetrahedron Letters, 36, p. 3031, 1995 DOI: 10.1016/0040-4039(95)00419-D

InChI:InChI=1/C12H20O4/c13-11-7-3-1-5-9(11)15-12(14)8-4-2-6-10(12)16-11/h9-10,13-14H,1-8H2

Upstream product

• 931-17-9 1,2-Cyclohexanediol 
• 6838-67-1 1,2-bis(trimethylsilyloxy)cyclohex-1-ene 
• 822-87-7 2-Chlorocyclohexanone 
• 533-60-8 cyclohexanone-2-ol 
• 141-28-6 diethyl adipate 
• 1792-81-0 cis-1,2-cyclohexane 

Downstream Products

• 26258-21-9 2,3,4,5,6,7-Hexahydro-1H-benzimidazol-2-on 
• 301651-23-0 N-(2-ethoxy-hexahydro-benzofuran-3a-yl)-O-methyl-hydroxylamine 

Relevant academic research and scientific papers

Chemoselective Pd-catalyzed oxidation of polyols: Synthetic scope and mechanistic studies

The regio- and chemoselective oxidation of unprotected vicinal polyols with [(neocuproine)Pd(OAc)]2(OTf)2 (1) (neocuproine = 2,9-dimethyl-1,10-phenanthroline) occurs readily under mild reaction conditions to generate α-hydroxy ketones. The oxidation of vicinal diols is both faster and more selective than the oxidation of primary and secondary alcohols; vicinal 1,2-diols are oxidized selectively to hydroxy ketones, whereas primary alcohols are oxidized in preference to secondary alcohols. Oxidative lactonization of 1,5-diols yields cyclic lactones. Catalyst loadings as low as 0.12 mol % in oxidation reactions on a 10 g scale can be used. The exquisite selectivity of this catalyst system is evident in the chemoselective and stereospecific oxidation of the polyol (S,S)-1,2,3,4-tetrahydroxybutane [(S,S)-threitol] to (S)-erythrulose. Mechanistic, kinetic, and theoretical studies revealed that the rate laws for the oxidation of primary and secondary alcohols differ from those of diols. Density functional theory calculations support the conclusion that β-hydride elimination to give hydroxy ketones is product-determining for the oxidation of vicinal diols, whereas for primary and secondary alcohols, pre-equilibria favoring primary alkoxides are product-determining. In situ desorption electrospray ionization mass spectrometry (DESI-MS) revealed several key intermediates in the proposed catalytic cycle.

Diastereoselective α-iminoamine rearrangement: Asymmetric synthesis of (R)-(-)- and (S)-(+)-2-benzyl-2-hydroxy-cyclohexanone

A convenient asymmetric synthesis of both (R)-(-)- and (S)-(+)-2- benzyl-2-hydroxycyclohexanones starting from racemic 2- benzyloxycyclohexanone and the chiral auxiliary 1-phenylethylamine is reported. The route involves a [1,3]-sigmatropic shift and a ne

Diastereo- and enantioselective synthesis of cis-2- hydroxycyclohexanamine and corresponding ethers by asymmetric reductive amination

A series of homochiral cis-2-alkoxy- and 2-aryloxyeyclohexanamines 5b- 5e has been synthesised by means of asymmetric reductive amination of the corresponding racemic 2-oxygenated cyclohexanones 2 with ee-values ranging from 95 to >99%. The respective 2-hydroxy and 2-cyclohexyl derivatives 5g-5h have been prepared from the 2-phenoxycyclohexanamine 4e. Relative and absolute stereochemistry has been elucidated.

N-Hydroxyphthalimide as an Effective Mediator for the Oxidation of Alcohols by Electrolysis

N-Hydroxyphthalimide is shown to be an effective electron carrier in the electrochemical oxidation of alcohols to the corresponding carbonyl compounds.