43006-74-2

Basic information

• Product Name: 3-deuterio-1-phenylpropan-1-one
• Synonyms: 3-deuterio-1-phenylpropan-1-one
• CAS NO: 43006-74-2
• Molecular Weight: 135.17
• Mol File: 43006-74-2.mol

Chemical Properties

• CAS DataBase Reference: 3-deuterio-1-phenylpropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deuterio-1-phenylpropan-1-one(43006-74-2)
• EPA Substance Registry System: 3-deuterio-1-phenylpropan-1-one(43006-74-2)

Safety Data

• Hazardous Substances Data: 43006-74-2(Hazardous Substances Data)

Upstream product

• 33716-94-8 1-phenyl<1-2H1>prop-2-en-1-ol 
• 768-03-6 Phenyl vinyl ketone 
• 557-20-0 diethylzinc 
• 100-47-0 benzonitrile 
• 560095-55-8 (1-phenyl-1-propen-3d₁-1-yl)pentamethyl phosphoric triamide 
• 4393-21-9 1-(phenyl)allylamine 
• 560095-43-4 (1-phenyl-2-propen-1-yl)amidophosphoric dichloride 
• 560095-46-7 C₁₃H₂₂N₃OP 
• 560095-49-0 (1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 100-52-7 benzaldehyde 
• 18026-91-0 deuterio-trimethyl-silane 
• 936-59-4 3-chloropropiophenone 

Relevant articles and documents

Manganese PNP-pincer catalyzed isomerization of allylic/homo-allylic alcohols to ketones-activity, selectivity, efficiency

We report the first manganese catalyzed isomerization of allylic alcohols to produce the corresponding carbonyl compounds. The ligand plays a decisive role in the efficiency of this reaction. Very high conversions could be obtained using a solvent-free reaction system. A detailed DFT study reveals a self-dehydrogenation/hydrogenation reaction mechanism which was verified by the isolation of the α,β-unsaturated ketone as intermediate and a deuterium labeling experiment. It also provided a rationale for the observed selectivity and the higher efficiency of phenyl over isopropyl substitution.

Additive-Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst

Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base increases the speed of the reaction drastically. Although some evidence was obtained supporting a dehydrogenation–hydrogenation mechanism, it was proven that this is not the major mechanism. Instead, the cobalt hydride complex formed by dehydrogenation of ethanol is capable of double-bond isomerization through alkene insertion–elimination.

Ruthenium-Catalyzed Redox Isomerizations inside Living Cells

Tailored ruthenium(IV) complexes can catalyze the isomerization of allylic alcohols into saturated carbonyl derivatives under physiologically relevant conditions, and even inside living mammalian cells. The reaction, which involves ruthenium-hydride intermediates, is bioorthogonal and biocompatible, and can be used for the "in cellulo" generation of fluorescent and bioactive probes. Overall, our research reveals a novel metal-based tool for cellular intervention, and comes to further demonstrate the compatibility of organometallic mechanisms with the complex environment of cells.

Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature

An environmentally benign method for the transformation of allylic alcohols into carbonyl compounds is described. Using [Rh(COD(CH3CN) 2]BF4 (2) in combination with 1,3,5-triaza-7- phosphaadamantane (PTA, 1) as the catalytic system in water results in a very fast redox isomerisation of a variety of secondary allylic alcohols at ambient temperature. Also, some primary allylic alcohols can be isomerised into the corresponding aldehydes. The active complex, which in some cases can be used in catalyst loadings as low as 0.5 mol%, is formed in situ from commercially available reagents. Based on deuterium labelling studies, a tentative mechanism involving metal-enone intermediates is presented.

Building molecular complexity via tandem ru-catalyzed isomerization/C-H activation

A tandem isomerization/C-H activation of a My lie alcohols was performed using a catalytic amount of RuCI2(PPh3)3. A variety of ortho alkylated ketones have been obtained in excellent yields. This tandem process relies on an in situ generation of a carbonyl functional group that directs the ortho C-H bond activation.

Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds

The catalytic activity of the ruthenium(II) complex [RuCp*(CH3CN)3][PF6] 1 in the transposition of allylic alcohols into carbonyl compounds, in acetonitrile, is reported. This catalyst has proven to be able to catalyze the transformation of poorly reactive and/or functionalized substrates under smooth conditions.

Cp*Ru(PN) complex-catalyzed isomerization of allylic alcohols and its application to the asymmetric synthesis of muscone

Highly efficient isomerization of allylic alcohols into saturated carbonyls is accomplished using the catalyst system of Cp*RuCl[Ph2P(CH2)2NH2-κ2-P,N]-KOt-Bu (Cp* = η5-C5(CH3)5) under mild conditions. Mechanistic consideration based on isotope-labeling experiments indicated the present reaction is applicable to the asymmetric isomerization of racemic sec-allylic alcohols with a prochiral olefin via dynamic kinetic resolution. A concise asymmetric synthesis of muscone has been achieved, where the asymmetric isomerization using an optically active ligand is a key reaction. Copyright

New ketone homoenolate anion equivalents derived from (alkenyl)pentamethyl phosphoric triamides

Lithiated ambident anions derived from (1-alkyl-2-propenyl)- or (1-phenyl-2-propenyl)-pentamethyl phosphoric triamides undergo regioselectively γ-reaction with various alkylating reagents and isobutyraldehyde. Further hydrolysis of adducts releases the ketone under acid conditions. Number of synthetic applications clearly show the ketone homoenolate behaviour of these new carbanions.

Primary 1-Arylcyclopropylamines from aryl cyanides with diethylzinc and titanium alkoxides

(Matrix presented) 1-Aryl-substituted primary cyclopropylamines are conveniently prepared from aromatic nitriles and diethylzinc. The yields range from 40 to 56% for donor-substituted (five examples) to 62-82% for non- and acceptor-substituted substrates

Rhodium promoted isomerisation of allylic alkoxides: A new method for enolate anion formation

Transition metal mediated isomerisation of allylic alkoxides is presented as a new method for enolate anion generation. The scope and limitations of enolate formation with the catalysts [Rh(dppe)(THF)2]+ClO4- and (Ph3P)3RhCl are explored and the synthetic potential of the methodology demonstrated in the stereoselective formation and reactions of certain ketone and aldehyde enolates.