76570-03-1Relevant academic research and scientific papers
Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks
Derosa, Joseph,Kang, Taeho,Tran, Van T.,Wisniewski, Steven R.,Karunananda, Malkanthi K.,Jankins, Tanner C.,Xu, Kane L.,Engle, Keary M.
, p. 1201 - 1205 (2020)
A nickel-catalyzed conjunctive cross-coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2-diarylated and 1,2-arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3-trifunctionalized building blocks using two-electron and one-electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2-diarylation of an alkene directed by a native carboxylate group.
Studies on Antifertility Agents: Part XLII - Synthesis and Antifertility Study of 6-Methoxy-3-phenyl-1-tetralin
Malik, Mangel S.,Rastogi, Shri Nivas
, p. 834 - 838 (2007/10/02)
LAH reduction of methyl β-(m-methoxyphenyl)-α-phenylpropionate (2) gives propanol 3 which after treatmeant with p-TsCl is reacted with KCN to yield the butyronitrile (5) and a mixture of isomeric propenes (6).Alkaline hydrolysis of 5 gives 7 which on cyclisation with PCl5-SnCl4 affords 6-methoxy-3-phenyl-1-tetralone (8).Reaction of Me2N(CH2)3MgCl with 8 furnishes the corresponding 1-substituted dihydronaphthalene (12).KBH4 reduction of 8 gives preferably 1,3-cis-tetralol (9a) as indicated by 13C-NMR and PMR data, NOE results and also by 13C-NMR data of its acetyl derivative (10). Condensation of 9a with PhOH-AlCl3 gives a mixture of products from which cis/trans-mixture of 1-(p-hydroxyphenyl) (13) and 1-(o-hydroxyphenyl) (14) derivatives and dialin (15) are obtained.Acetylation of 13 (a mixture of two isomers in 55:45 proportion as shown by GLC) and 14 with Ac2O-pyridine gives the corresponding acetoxy derivatives (16 and 17).Compound 13 on condensation with β-chloroethylpyrrolidine affords the title compound (18).In female albino rats, compound 18 does not prevent pregnancy at 10 mg/kg dose.As 18 is a mixture no inference can be had about the receptor site.
Lithium keten thioacetalides. Factors influencing α- versus γ-alkylation
Murphy, William S.,Wattanasin, Sompong
, p. 2678 - 2682 (2007/10/02)
Alkylation of the lithium salt of the vinyl-1,3-dithian (2; R = CH 3) occurred exclusively at the α-carbon. However both α- and γ-alkylation was observed with the substrate (2; R = C 6H5). A systematic investigation reveal
