16460-85-8

Basic information

• Product Name: 2-Hexanone, 4-phenyl-, (S)-
• CAS NO: 16460-85-8
• Molecular Formula: C12H16O
• Molecular Weight: 176.258
• Mol File: 16460-85-8.mol
• Article Data: 54

Chemical Properties

• CAS DataBase Reference: 2-Hexanone, 4-phenyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hexanone, 4-phenyl-, (S)-(16460-85-8)
• EPA Substance Registry System: 2-Hexanone, 4-phenyl-, (S)-(16460-85-8)

Safety Data

• Hazardous Substances Data: 16460-85-8(Hazardous Substances Data)

Upstream product

• 56422-91-4 (E)-4-phenyl-3-hexen-2-one 
• 93-55-0 1-phenyl-propan-1-one 
• 1528-59-2 3-phenyl-pent-2-enoic acid ethyl ester 
• 97-93-8 triethylaluminum 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 100-52-7 benzaldehyde 
• 91667-21-9 (Z)-4-phenyl-3-hexen-2-one 
• 557-20-0 diethylzinc 
• 22174-65-8 (Z,E)-4-phenyl-3-hexen-2-one 
• 1896-62-4 (E)-benzalacetone 
• 937-53-1 (Z)-4-phenylbut-3-en-2-one 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 67-64-1 acetone 
• 811-49-4 ethyllithium 

Relevant articles and documents

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Mechanistic-Insight-Driven Rate Enhancement of Asymmetric Copper-Catalyzed 1,4-Addition of Dialkylzinc Reagents to Enones

The combination of [Cu(MeCN)4]TFA·TFAH (TFA = O2CCF3) with Feringa's phosphoramidite ligand (LA) provides an exceptionally active (0.75 mol %) catalyst for asymmetric conjugate additions of ZnR2 (R = Et and Me at -40 to -80 °C) to enones. Kinetic and other studies of the addition of ZnEt2 to cyclohex-2-en-1-one indicate a transition state stoichiometry composition of (ZnEt2)3(enone)4Cu2(LA)3 that is generated by transmetalation from Et2Zn(enone)2. Catalyst genesis is significantly slower than turnover (which has limited previous attempts to attain useful kinetic data); in the initial stages, varying populations of catalytically inactive, off-cycle, species are present. These issues are overcome by a double-dose kinetic analysis protocol. A rest state of [LACu(Et)(μ-TFA)(μ-{(enone)(ZnEt)2(enolate)})CuLA2]+ (through the equivalence of enolate = enone + ZnEt2) is supported by DFT studies (ωB97X-D/SRSC). Rate-determining ZnEt2(enone)2 transmetalation drives the exceptionally high catalytic activity of this system.

Enantiopure sulfoximines-catalyzed 1, 4-additions to 2-en-ketone

An efficient chiral catalyst procedure for the preparation of β-chiral ketone via the 1, 4-additions reaction of 2-en-ketone has been developed using enantiopure sulfoximines modified with functional groups as ligands. The carefully design and synthesized