1286722-86-8

Basic information

• Product Name: C₂₀H₁₉F₃O₄
• CAS NO: 1286722-86-8
• Molecular Weight: 380.364
• Mol File: 1286722-86-8.mol

Chemical Properties

• CAS DataBase Reference: C₂₀H₁₉F₃O₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₀H₁₉F₃O₄(1286722-86-8)
• EPA Substance Registry System: C₂₀H₁₉F₃O₄(1286722-86-8)

Safety Data

• Hazardous Substances Data: 1286722-86-8(Hazardous Substances Data)

Upstream product

• 13505-39-0 3-hydroxy-1-phenyl-butan-1-one 
• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 
• 105735-20-4 (3S)-(+)-3-hydroxy-1-phenylbutan-1-one 
• 98-86-2 acetophenone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 116660-74-3 (-)-(3R)-3-hydroxy-1-phenylbutan-1-one 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 

Relevant articles and documents

Synthesis and Suzuki-Miyaura cross-coupling of enantioenriched secondary potassium β-trifluoroboratoamides: Catalytic, asymmetric conjugate addition of bisboronic acid and tetrakis(dimethylamino)diboron to α,β- unsaturated carbonyl compounds

Enantioenriched potassium β-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)-diboron to α,β-Unsaturated amides. These dibora reagents provide access to the desired organotri-fluoroborates using effective and atom economical sources of boron. The copper-catalyzed β-boration is extended to α,β- Unsaturated ketones and esters. The desired potassium organotrifluoroborates are synthesized with yields up to 92% and enantiomeric ratios up to 98:2. The enantioenriched potassium btrifluoroboratoamides are successfully cross-coupled with an array of aryl and heteroaryl chlorides in high yield with complete stereochemical fidelity as the transmetalation proceeds through an SE2 mechanism via an open transition state.

Albumin-directed stereoselective reduction of 1,3-diketones and β-hydroxyketones to anti diols

The reduction of 1,3-diketones and β-hydroxyketones with NaBH 4 in aqueous acetonitrile is highly stereoselective in the presence of stoichiometric amounts of bovine or human albumin, giving anti 1,3-diols with d.e. up to 96%. The same reaction, without albumin, gives syn and anti 1,3-diols in approximately 1:1 ratio. The presence of an aromatic carbonyl group is essential for diastereoselectivity in the NaBH4/albumin reduction of both 1,3-diketones and β-hydroxyketones. Thus, 3-hydroxy-1-(p-tolyl)-1- butanone is stereoselectively reduced in the presence of albumin, while reduction of its isomer 4-(p-tolyl)-4-hydroxy-2-butanone is not stereoselective. The albumin-controlled reduction is not stereospecific as both enantiomers of 1-aryl-3-hydroxy-1-butanones are reduced to diols with identical stereoselectivities. Circular dichroism of the bound substrates confirms that aromatic ketones are recognized by the protein's IIA binding site. Binding studies also suggest that 1,3-diketones are recognized in their enol form. From the effect of pH on binding of a diketone it is concluded that, in the complex with the substrate, ionizable residues His242 and Lys199 are in the neutral and protonated forms, respectively. A homology model of BSA was obtained and docking of model substrates confirms the preference of the protein for aromatic ketones. Modelling of the complexes with the substrates also allows us to propose a mechanism for the reduction of 1,3-diketones in which the chemoselective reduction of the first (aliphatic) carbonyl is followed by the diastereoselective reduction of the second (aromatic) carbonyl. The role of albumin is thus a combination of chemo- and stereocontrol.