153737-64-5

Basic information

• Product Name: 5-Hexen-2-one, 3-methyl-6-phenyl-, (5E)-
• CAS NO: 153737-64-5
• Molecular Formula: C13H16O
• Molecular Weight: 188.269
• Mol File: 153737-64-5.mol

Chemical Properties

• CAS DataBase Reference: 5-Hexen-2-one, 3-methyl-6-phenyl-, (5E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hexen-2-one, 3-methyl-6-phenyl-, (5E)-(153737-64-5)
• EPA Substance Registry System: 5-Hexen-2-one, 3-methyl-6-phenyl-, (5E)-(153737-64-5)

Safety Data

• Hazardous Substances Data: 153737-64-5(Hazardous Substances Data)

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 153737-63-4 (CH₃CH₂CH₂CH₂)3SnOC(CH₃)CHCH₃ 
• 814-78-8 3-Methyl-3-buten-2-one 
• 536-74-3 phenylacetylene 
• 162707-93-9 (E)-3-(Benzothiazol-2-ylsulfanyl)-3-methyl-6-phenyl-hex-5-en-2-one 
• 300-57-2 allylbenzene 
• 815-57-6 3-Methyl-2,4-pentanedione 
• 821770-42-7 (E)-1-diphenylphosphinoyl-3-methyl-6-phenyl-hex-5-en-2-one 
• 7422-28-8 (E)-2-phenylethenyl(trimethyl)stannane 
• 87802-71-9 (E)-methyl cinnamyl carbonate 

Downstream Products

• 384333-15-7 3-methoxy-6-methyl-6-(3-phenyl-2-propenyl)-2-cyclohexen-1-one 
• 384332-91-6 4-methyl-4-[3-phenyl-(2E)-propenyl]-1,3-cyclohexanedione 

Relevant articles and documents

Double Alkylation of Tin Enolate Derived from Diketene and Bis(tributyltin) Oxide

Tin enolate derived from diketene and (n-Bu3Sn)2O was alkylated by alkyl halides, leading to mono-alkylated enolate via facile decarboxylation, which successively react with other electrophiles like an aldehyde and alkyl halides to furnish double-alkylated acetones.

Palladium(II)-Catalyzed Deacylative Allylic C-H Alkylation

The first deacylative allylic C-H alkylation has been established by employing the palladium-catalyzed allylic C-H activation and decarboxylative nucleophile generation. A wide scope of nucleophiles are tolerated and densely functionalized alkylation products turn out to be furnished in moderate to good yield. More importantly, this strategy provides an alternative method for the allylic C-H alkylation with less stabilized carbon nucleophiles, and can be further expanded to the synthesis of unconjugated enynes.

Synthesis of trans-disubstituted alkenes by cobalt-catalyzed reductive coupling of terminal alkynes with activated alkenes

A cobalt-catalyzed reductive coupling of terminal alkynes, RC≡CH, with activated alkenes, R'CH=CH2, in the presence of zinc and water to give functionalized trans-disubstituted alkenes, RCH=CHCH2CH 2R', is described. A variety of aromatic terminal alkynes underwent reductive coupling with activated alkenes including enones, acrylates, acrylonitrile, and vinyl sulfones in the presence of a CoCl2/P(OMe) 3/Zn catalyst system to afford 1,2-trans-disubstituted alkenes with high regio- and stereoselectivity. Similarly, aliphatic terminal alkynes also efficiently participated in the coupling reaction with acrylates, enones, and vinyl sulfone, in the presence of the CoCl2/P(OPh)3/Zn system providing a mixture of 1,2-trans- and 1,1-disubstituted functionalized terminal alkene products in high yields. The scope of the reaction was also extended by the coupling of 1,3-enynes and acetylene gas with alkenes. Furthermore, a phosphine-free cobalt-catalyzed reductive coupling of terminal alkynes with enones, affording 1,2-trans-disubstituted alkenes as the major products in a high regioisomeric ratio, is demonstrated. In the reactions, less expensive and air-stable cobalt complexes, a mild reducing agent (Zn) and a simple hydrogen source (water) were used. A possible reaction mechanism involving a cobaltacyclopentene as the key intermediate is proposed. Copyright

Diphenylphosphinoyl-mediated synthesis of ketones

α-Diphenylphosphinoyl ketones are selectively and sequentially alkylated at the α-position. Double lithiation and selective alkylation occurs at the less stabilised γ-position. Dephosphinoylation of the alkylation products gives ketones. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible. The method is ideally suited for the preparation of acid-sensitive ketones. The Royal Society of Chemistry 2006.

Rhodium-catalyzed conjugate addition of aryl- and alkenyl-stannanes to α,β-unsaturated carbonyl compounds

The addition of aryl- or alkenyl-trimethylstannanes to α,β-unsaturated carbonyl compounds in the presence of a catalytic amount of a cationic rhodium complex ([Rh(cod)(MeCN)2]BF4) and water to afford the conjugate addition products in good yields was examined. It was observed that addition of water was necessary for the reaction to proceed smoothly. The aryl- or alkenyl-rhodium complex, which is generated by the transmetalation from the organotin compound, is considered to be the active catalytic species.

Dephosphorylation of α-fully substituted β-keto phosphonates with LiAlH4; regioselective alkylation of ketones employing phosphonate as a temporary activating group

Alkylation of β-keto phosphonates is performed by treatment of β-keto phosphonates with n-BuLi, followed by addition of alkyl halides. The acquired α-fully substituted β-keto phosphonates are dephosphonylated by treatment of the lithium enolates with LiAlH4, followed by quenching with aqueous H2SO4 solution. This whole procedure represents a new route to regioselective alkylation of ketones.

Palladium-catalysed Synthesis of α-Diallylated Ketosulphides of Benzothiazole and their Transformation into Diallyl Thiiranes and Trienes

α-Ketosulphides of benzothiazole 1 react with allylic carbonates in the presence of palladium acetate in dichloromethane under mild conditions affording α,α-diallylated ketosulphides 2 in high yields.Reduction of 2 with sodium borohydride in isopropanol gives episulphides which in turn can be transformed almost quantitatively into trienes.