33599-88-1

Basic information

• Product Name: 5-Hexen-2-one, 6-phenyl-, (5E)-
• CAS NO: 33599-88-1
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Mol File: 33599-88-1.mol
• Article Data: 47

Chemical Properties

• CAS DataBase Reference: 5-Hexen-2-one, 6-phenyl-, (5E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hexen-2-one, 6-phenyl-, (5E)-(33599-88-1)
• EPA Substance Registry System: 5-Hexen-2-one, 6-phenyl-, (5E)-(33599-88-1)

Safety Data

• Hazardous Substances Data: 33599-88-1(Hazardous Substances Data)

Upstream product

• 4173-44-8 (E,E)-6-phenyl-3,5-hexadien-2-one 
• 100-42-5 styrene 
• 78-94-4 methyl vinyl ketone 
• 536-74-3 phenylacetylene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 61363-91-5 (E)-(3-phenylallyl) 3-oxo-butyrate 
• 112163-00-5 (+/-)-1-phenylallyl acetoacetate 
• 104910-34-1 3-phenylsulfonyl-6-phenyl-5-hexen-2-one 
• 28483-60-5 Acetonyltributylstananne 
• 4392-24-9 Cinnamyl bromide 
• 588-73-8 (Z)-β-bromostyrene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 1833-53-0 2-(Trimethylsilyloxy)propene 

Downstream Products

• 89849-53-6 (5E)-6-phenylhex-5-en-2-one (E)-oxime 
• 1219090-54-6 (E)-1-(5-bromo-4-methoxy-2-(methoxymethoxy)phenyl)-1-hydroxy-7-phenylhept-6-en-3-one 
• 1348480-53-4 (E)-1-methyl-5-phenylpent-4-enylamine 
• 87109-43-1 (E)-2-methyl-2-(4-phenylbut-3-en-1-yl)-1,3-dioxolane 

Relevant articles and documents

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Covalent Organic Framework as a Heterogeneous Ligand for the Regioselective Oxidative Heck Reaction

A simple imine-based covalent organic framework (COF) as heterogeneous ligand for PdII-promoted Heck reaction is reported. Good regioselectivity for a wide range of electronically unbiased olefins is obtained (linear/branched >100:1 in most cases). Related tests and density functional theory calculations are used to explore the reason underlying the high selectivity. This research opens a route for COF as an intriguing platform to control regioselectivity catalysis.

Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones

The scope of the triphenylphosphine oxide-catalyzed reduction of conjugated polyunsaturated ketones using trichlorosilane as the reducing reagent has been examined. In all cases studied, the α,β-C=C double bond was selectively reduced to a C-C single bond while all other reducible functional groups remained unchanged. This reaction was applied to a large variety of conjugated dienones, a trienone, and a tetraenone. Additionally, a tandem one-pot Wittig/conjugate-reduction reaction sequence was developed to produce γ,δ-unsaturated ketones directly from simple building blocks. In these reactions the byproduct of the Wittig reaction served as the catalyst for the reduction reaction. This strategy was then used in the synthesis of naturally occurring moth pheromones to demonstrate its utility in the context of natural-product synthesis.