1379077-30-1

Basic information

• Product Name: (S)-2-((R)-(2,4-bis(trifluoromethyl)phenyl)(hydroxy)methyl)cyclohexanone
• CAS NO: 1379077-30-1
• Molecular Weight: 340.265
• Mol File: 1379077-30-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-((R)-(2,4-bis(trifluoromethyl)phenyl)(hydroxy)methyl)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-((R)-(2,4-bis(trifluoromethyl)phenyl)(hydroxy)methyl)cyclohexanone(1379077-30-1)
• EPA Substance Registry System: (S)-2-((R)-(2,4-bis(trifluoromethyl)phenyl)(hydroxy)methyl)cyclohexanone(1379077-30-1)

Safety Data

• Hazardous Substances Data: 1379077-30-1(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 59664-42-5 2,4-bis(trifluoromethyl)benzaldehyde 

Relevant articles and documents

Catalytic anions embedded into avidin: Importance of their chirality and the chiral environment on the stereocontrol of the aldol reaction

Several catalytic anions bearing a pseudo-dipeptide scaffold, in combination with a biotinylated imidazolium cation, were prepared. The assembly of these salts with avidin resulted in the formation of stable biohybrid catalysts, active in ionic liquid/aqueous media for the aldol reaction. By using natural and non-natural amino alcohols as "side chains" for the proline derivative anion, we studied the cooperativity between the anion and its position in avidin. Taking advantage of the large freedom of movement of the anion inside avidin, we also investigated the substrate scope of this type of biohybrid catalyst.

Direct asymmetric aldol reactions in water catalysed by a highly active C2-symmetrical bisprolinamide organocatalyst

A novel C2-symmetrical bisprolinamide organocatalyst was synthesised and used to facilitate asymmetric direct aldol reactions in a water emulsion. Reactions were performed at room temperature with very low catalyst loadings (1-2.5 mol%) without the required use of additives, co-catalysts or extended reaction times (24 h). This catalyst system was then used with a variety of aldehyde substrates showing good reaction generality for benzaldehydes with cyclohexanone (dr range 77/23 to 99/1, anti/syn; ee range 33% to 99%) and moderate scope with cyclopentanone (dr range 45/55 to 76/24, anti/syn; ee range 14% to 68%). Ultra-low catalysts loadings (0.1 and 0.05 mol%) were also investigated demonstrating catalyst turnover numbers in the order of 1000.

Asymmetric aldol reaction catalyzed by the anion of an ionic liquid

Herein we report the synthesis of a chiral imidazolium salt derived from trans-l-hydroxyproline and its applications as a catalyst for the asymmetric aldol reaction. By performing the aldol reaction in [Bmim]NTf2 as a solvent, we report excellent isolated yields of the aldol product (up to 99%), as well as modest to excellent selectivities (dr superior to 99:1. ee up to 89%). Mechanistic insights and the origins of the selectivity of the aldol reaction are discussed on the basis of the results obtained with two catalytic imidazolium salts having different H-bonding potential.