5638-30-2

Upstream product

• 18986-66-8 methyl 5-phenylcyclohexane-1,3-dione 
• 75-35-4 1,1-Dichloroethylene 
• 27059-47-8 1-phenyl-1-chloropentane 
• 6966-37-6 DL-ethyl-3-hydroxy-3-phenyl heptanoate 
• 109-72-8 n-butyllithium 
• 140-10-3 (E)-3-phenylacrylic acid 
• 97023-56-8 (E)-3-phenylhept-2-enoic acid 
• 109-65-9 1-bromo-butane 
• 17377-82-1 (E)-1-methylpropyl cinnamate 
• 220629-77-6 (1-Phenylpentyl)propanedioic acid 
• 63473-85-8 ethyl 3-phenylheptanoate 
• 693-04-9 butyl magnesium bromide 
• 621-82-9 Cinnamic acid 
• 583-03-9 1-Phenyl-1-pentanol 

Downstream Products

• 63473-85-8 ethyl 3-phenylheptanoate 
• 95698-46-7 3-phenyl-heptanoic acid-(4-bromo-phenacyl ester) 
• 30368-28-6 5-Phenylnonansaeuremethylester 
• 63049-32-1 2-Methylthio-3-phenylheptansaeure 
• 220629-78-7 3-Phenylheptanoyl chloride 
• 185674-73-1 2-Diazo-5-phenylnonan-3-one 
• 114376-30-6 3-Phenyl-1-heptanol 
• 63049-43-4 2-Phenylhexanaldimethylacetal 

Relevant academic research and scientific papers

Conjugate addition of RMgX-3MeLi to α,β-unsaturated amides and α,β-unsaturated carboxylic acids

In the presence of 3 equivalents of MeLi, various Grignard reagents reacted with secondary α,β-unsaturated amides and α,β-unsaturated carboxylic acids to give the corresponding Michael adducts in good yields. Copyright

Efficient kinetic resolution in the asymmetric hydrosilylation of imines of 3-substituted indanones and 4-substituted tetralones

Kinetic resolution of the N-methyl imines of 3-substituted indanones and 4-substituted tetralones could be accomplished by hydrosilylation with a chiral titanocene catalyst. N-Methyl imines of 4-substituted tetralones were resolved to yield, after hydrolysis of the unreacted starting materials, ketones with high ee's and the amine products with high diastereomeric and enantiomeric purity. The utility of this process was demonstrated in the synthesis of sertraline.

Reactions d'addition conjuguee d'organolithiens aux acides carboxyliques α, β-insatures

In THF at -78 deg C, organolithium derivatives and unprotected α,β-unsaturated carboxylic acids give a conjugated addition reaction. Reactions of 1- and 2-napthoic acids with various organolithium derivatives and electrophiles are reported. Two X-ray studies show that the reaction occurs with a good diastereoselectivity: the dilithiated enolate formed as an intermediate adds the electrophile exclusively via the face opposite to that of the organolithium. A study of the 1H NMR spectra of the products obtained shows that these compounds adopt a preffered conformation in solution. The protonolysis of the intermediate enolate by trifluoroacetic acid in an inverted mode gives rise to the formation of 1,2-disubstituted dihydronapthalenes. With acyclic α,β-unsaturated carboxylic acids, the diastereoselectivity of the reaction is marginal. With secondary butyllithium, the protonolysis of the intermediate enolates gives a 1,4-addition and an average diastereoselectivity. Reaction of phenylpropiolic acid with butyllithium gives rise to the formation of a produst resulting from a trans addition to the triple bond; the organolithium derivative adds in α to the carboxylic group. - Key words: 1,4-addition reactions; carboxylic acids; organolithium derivatives.

Stereocontrol in the intramolecular Buchner reaction of diazoketones

Rhodium(II) acetate catalysed intramolecular Buchner cyclisation of a series of diazoketones 1 proceeds with excellent diastereoselectivity to produce the trans substituted azulenones 2, which exist as a rapidly equilibrating cycloheptatriene-norcaradiene system, from which the norcaradiene tautomers can be efficiently trapped as PTAD cycloadducts 4. The cyclisation-cycloaddition sequence can be conducted in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case. In the reaction of diazoketone If intramolecular cyclopropanation competes with cyclisation to the aromatic ring.

Directed conjugate addition of organolithium reagents to α,β-unsaturated carboxylic acids

α,β-Unsaturated carboxylic acids undergo predominantly conjugate addition with organolithium reagents at low temperature (-78 °C) in THF and lead to various substituted alkanoic acids after quenching with electrophiles; with (E)-3-phenylpropenoic acid, this tandem alkylation sequence also affords significant amounts of isomeric 1,3-addition products.

Contrasting behaviour of (E)-3-(trimethylsilyl)- and (E)-3-phenylpropenoic acids towards n-butyl- and tert-butyllithium

The title compounds 2 and 9 react with tert-buthyllithium to give considerable amounts of 'anti-Michael' adducts 3 and 10, respectively, in which the tert-butyl group is bonded to C-2.A single-electron-transfer (SET) mechanism is proposed for these reacti