5650-07-7

Basic information

• Product Name: Phenyl(2-methyl-1-propenyl) ketone
• Synonyms: 3-Methyl-1-phenyl-2-buten-1-one;Phenyl(2-methyl-1-propenyl) ketone;Phenylisobutenyl ketone;Seneciophenone
• CAS NO: 5650-07-7
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.2124
• Mol File: 5650-07-7.mol
• Article Data: 67

Chemical Properties

• Boiling Point: 243.2°Cat760mmHg
• Flash Point: 95.3°C
• Appearance: /
• Density: 0.977g/cm³
• Vapor Pressure: 0.0325mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: Phenyl(2-methyl-1-propenyl) ketone(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl(2-methyl-1-propenyl) ketone(5650-07-7)
• EPA Substance Registry System: Phenyl(2-methyl-1-propenyl) ketone(5650-07-7)

Safety Data

• Hazardous Substances Data: 5650-07-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 23, p. 106, 1958 DOI: 10.1021/jo01095a614Synthesis, p. 130, 1977 DOI: 10.1055/s-1977-24297

InChI:InChI=1/C11H12O/c1-9(2)8-11(12)10-6-4-3-5-7-10/h3-8H,1-2H3

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 2674-04-6 diphenyl cadmium 
• 64097-38-7 2,3-dibromo-3-methyl-1-phenylbutan-1-one 
• 74-85-1 ethene 
• 98-88-4 benzoyl chloride 
• 71-43-2 benzene 
• 43108-74-3 3-hydroxy-3-methyl-1-phenyl-1-butanone 
• 62269-40-3 2-Chlor-3-methyl-1-oxo-1-phenyl-2-buten 
• 57205-23-9 3-Methyl-1-phenyl-2-phenylseleno-1-butanon 
• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 29917-94-0 2-methylprop-1-enyllithium 
• 67-56-1 methanol 
• 917-64-6 methyl magnesium iodide 
• 185245-65-2 3-methylthio-3-N-piperidino-1-phenyl-2-propen-1-one 

Downstream Products

• 128259-95-0 3,3-dimethyl-4-nitro-1-phenyl-pentan-1-one 
• 128259-94-9 3,3-dimethyl-4-nitro-1-phenyl-butan-1-one 
• 105337-08-4 4-methyl-2-phenylpent-3-en-2-ol 
• 69096-81-7 3-methyl-1,3-ddiphenylbutan-1-one 
• 39533-27-2 4-methyl-6-phenyl-[1,2]oxathiin-2,2-dioxide 
• 582-62-7 3-methyl-1-phenylbutan-1-one 
• 64097-38-7 2,3-dibromo-3-methyl-1-phenylbutan-1-one 
• 16492-53-8 5,5-dimethyl-1,3-diphenyl-4,5-dihydro-1H-pyrazole 
• 53440-63-4 4,4-dimethyl-6-phenyl-3,4-dihydro-[1,3]oxazin-2-one 
• 56563-89-4 3-Allylthio-3-methyl-butyrophenon 
• 38010-34-3 (E)-2-Ethyl-3-hydroxy-3-methyl-5-phenyl-pent-4-enenitrile 
• 56641-10-2 3-Crotylthio-3-methyl-butyrophenon 
• 38010-47-8 (E)-3-Hydroxy-2,2,3-trimethyl-5-phenyl-pent-4-enenitrile 
• 58006-78-3 4,7-dihydro-7,7-dimethyl-5-phenyl-1,2,4-oxadiazepin-3(2H)-one 

Relevant articles and documents

Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay

We report a stereoselective formal [3 + 2] cycloaddition of cyclopropyl ketones and radical-acceptor alkenes to form polysubstituted cyclopentane derivatives. Catalyzed by a chiral Ti(salen) complex, the cycloaddition occurs via a radical redox-relay mechanism and constructs two C-C bonds and two contiguous stereogenic centers with generally excellent diastereo- and enantioselectivity.

Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols

The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.

Pd-catalyzed imine-directed intramolecular C–N bond formation through C(sp3)–H activation: An efficient approach to multisubstituted pyrroles

An atom-economic approach to synthesize 1,2,4-trisubstituted pyrroles through palladium-catalyzed imine-directed intramolecular C(sp3)–H amination reaction has been developed. The imine group acts as a directing group as well as an intramolecular nucleophile for the first time in intramolecular C–N bonds formation reactions.

Nickel-Catalyzed Chemoselective Asymmetric Hydrogenation of α,β -Unsaturated Ketoimines: An Efficient Approach to Chiral Allylic Amines

An efficient synthetic route to chiral allylic amines has been developed by nickel/(S,S)-Ph-BPE complex catalyzed chemoselective asymmetric hydrogenation of α,β-unsaturated ketoimines. Varieties of α,β-unsaturated ketoimines have been well tolerated in this transformation to give chiral allylic amines with high yields and excellent ee values (up to 99% yield, up to 99% ee). A gram-scale reaction with 0.2 mol % catalyst loading has also been achieved.