84624-42-0

Basic information

• Product Name: threo-2-cyclohexanone
• Synonyms: threo-2-cyclohexanone
• CAS NO: 84624-42-0
• Molecular Weight: 234.295
• Mol File: 84624-42-0.mol

Chemical Properties

• CAS DataBase Reference: threo-2-cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: threo-2-cyclohexanone(84624-42-0)
• EPA Substance Registry System: threo-2-cyclohexanone(84624-42-0)

Safety Data

• Hazardous Substances Data: 84624-42-0(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 91890-07-2 2-(1-cyclohexenyloxy)-1,3,2-dioxaborolane 
• 104412-60-4 cyclohexen-1-yloxybis(dimethylamino)borane 
• 104412-62-6 (1-cyclohexenyloxy)dimethoxyborane 
• 17814-55-0 trichloro<(1-cyclohexenyl)oxy>silane 

Downstream Products

• 108-94-1 cyclohexanone 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant articles and documents

Highly efficient direct a larger-scale aldol reactions catalyzed by a flexible prolinamide based-metal Lewis acid bifunctional catalyst in the presence of water

In this work, four prolinamide-based organocatalysts were readily synthesized and applied to the asymmetric direct aldol reactions of ketones and aromatic aldehydes in the presence of water. When TFA was used as an acidic additive, 10 mol % loading of 1c

Highly efficient asymmetric aldol reaction in brine using a fluorous sulfonamide organocatalyst

A fluorous organocatalyst promotes direct asymmetric aldol reactions of aromatic aldehydes with ketones in brine to afford the corresponding anti-aldol products in high yield with up to 96% ee. Fluorous organocatalyst can be readily recovered by solid phase extraction using fluorous silica gel and reused without purification. The Royal Society of Chemistry 2012.

Proline-functionalized magnetic core-shell nanoparticles as efficient and recyclable organocatalysts for aldol reactions

Novel magnetically tagged organocatalysts have been developed based on core-shell nanoparticles consisting of magnetite cores and polyacrylate shells containing 4-hydroxyproline moieties. These catalysts allow the performance of direct asymmetric aldol re

An environmentally friendly Mukaiyama aldol reaction catalyzed by a strong Bronsted acid in solvent-free conditions

o-Benzenedisulfonimide, a new strong bench-stable Bronsted acid, has been shown to efficiently catalyze the Mukaiyama aldol reaction of aldehydes or dimethyl acetals with silyl enol ethers under mild solvent-free reaction conditions.

Asymmetrie retro- and transfer-aldol reactions catalyzed by a simple chiral primary amine

(Chemical Figure Presented) One stone four birds: A single chiral primary amine was found to catalyze unprecedented asymmetric retro-aldol and transfer-aldol reactions, leading to four different chiral aldol adducts from one common chiral source with up to 99:1 d.r. and 99% ee (see scheme).

Effects of magnesium salts and amines on the stereoselectivity in the imine aldol reaction

In the imine aldol reactions of 1 with aromatic aldehydes using magnesium salts in the presence of amines, the threo/erythro ratios of products increased in the order Mg(ClO4)2>MgI2>MgBr 2>MgCl2>Mg(OTf)2 and N,N,N′, N′-tetramethylethylenediamine (TMEDA)>Et3N. This increase in the threo/erythro ratios of products was estimated to be caused by a retro-imine aldol reaction under thermodynamic control.

Highly diastereo- and enantioselective direct aldol reactions of aldehydes and ketones catalyzed by siloxyproline in the presence of water

Proline-based organocatalysts have been developed for a highly enantioselective, direct aldol reaction of aldehydes and ketones in the presence of water. While several surfactant-proline combined catalysts have proved effective, proline derivatives with a hydrophobic moiety such as rraw-siloxy-L-proline and cis-siloxy-D-proline, both of which are easily prepared from the same commercially available 4-hydroxy-L-proline. have been found to be the most effective organocatalysts examined in this study, affording the aldol product with excellent diastereo- and enantioselectivities, these two catalysts generating opposite enantiomers. Water affects the selectivity, and poor results are obtained under neat reaction conditions or in dry organic solvents. More than three equivalents of water are required for the best diastereo- and enantioselectivities. while three equivalents is the recommended amount from a synthetic point of view. The reaction proceeds in the organic phase, and also proceeds in the presence of a large amount of water. The large-scale preparation of aldols with the minimal use of an organic solvent, including in the purification step. is described.

cis-4-pyrrolidin-1-yl-L-proline: A highly stereoselective organocatalyst for the direct aldol reaction

Modification of the pyrrolidinyl backbone of proline has not been quite successful for improving the catalytic efficiency and enantioselectivity. In this study, cis substitutions on the C4 position of proline with nitrogen-containing groups were found to

A polymer-supported phosphoramide as a Lewis-base catalyst for the catalytic aldol reaction

The aldol reactions between trichlorosilyl enol ethers and aldehydes were catalyzed by an environmentally benign polymer-supported phosphoramide organocatalyst. Eight examples are reported with moderate to good chemical yields and stereoselectivity. Signi

Surface-mediated solid phase reaction. I. Aldol reaction of silyl enol ethers with aldehydes on a solid surface of neutral alumina: Selectivity for anti aldols

The aldol reaction of trimethyl silyl enol ethers with aldehydes on the solid surface of neutral alumina under sonication without any solvent is found to proceed providing cross aldol products with anti selectivity.