31706-57-7

Usage

Synthesis Reference(s)

Tetrahedron Letters, 12, p. 951, 1971 DOI: 10.1016/S0040-4039(01)96597-9

InChI:InChI=1/C11H12O/c1-8-2-3-10-7-11(12)5-4-9(10)6-8/h2-3,6H,4-5,7H2,1H3

Upstream product

• 1190847-95-0 C₁₅H₂₄O₃ 
• 103040-39-7 3-(3-methylphenyl)propionyl chloride 
• 26386-94-7 2-methyl-6-methoxynaphthalene 

Downstream Products

• 1345122-20-4 N-[5-(7,7-difluoro-3-methyl-5,6,7,8-tetrahydronaphthalen-2-yl)(2-pyridyl)](2,6-difluorophenyl)carboxamide 
• 134698-07-0 1'-benzyl-3,4-dihydro-6-methylspiro(naphthalene-1(2H),4'-piperidine) 
• 1025918-63-1 2-Benzylamino-6-methyl-1,2,3,4-tetrahydro-naphthalene-2-carbonitrile 
• 1027153-23-6 (2-Aminomethyl-6-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-benzyl-amine 
• 1026636-85-0 Benzyl-(6-methyl-3,4-dihydro-naphthalen-2-yl)-amine 
• 134697-66-8 1'-benzyl-3,4-dihydro-6-methyl-2-oxospiro 

Relevant academic research and scientific papers

A concise method for the synthesis of 2-tetralone by titanium tetrachloride-promoted cyclization of 4-aryl-2-hydroxybutanal diethyl acetal

4-Aryl-2-hydroxybutanal diethyl acetal, prepared from the reaction of benzyl Grignard reagent and glycidaldehyde diethyl acetal, was treated with titanium tetrachloride to give 2-tetralone in good yield. This highly efficient transformation involves tande

The Intramolecular Buchner Reaction of Aryl Diazoketones. Substituent Effects and Scope in Synthesis

Rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acid produces bicyclodecatrienones or 2-tetralones depending on the substitution pattern of the aryl ring in the precursor; the former products are transformed into the latter catalytically with trifluoroacetic acid.Precursors with methyl, methoxy, and acetoxy substituents have been examined, efficient cyclisation occurring in all cases.When the precursor contains a meta-methoxy substituent, 2-tetralones are obtained directly.The efficient conversion of 3-phenylpropionicacid into trans-1-methylbicyclodecan-2-one is also described, partial asymmetric synthesis having been realised through the use of rhodium (S)-mandelate as the cyclisation catalyst.Cyclisations of diazoketones derived from 4-phenylbutyric acid and 5-phenylpentanoic acid have also been studied; the former provides a new entry into the bicycloundecane system whereas the latter produces a 2,3-disubstituted cyclopentanone via C-H insertion.Aspects of the cycloheptatriene-norcaradiene equilibrium in fused ring systems are discussed.

REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)CYCLOALKENONES AND OF α-PHENYL-α-(PHENYLTHIO)KETONES VIA αα-ADDITION OF PHENYLSULPHENYL CHLORIDE TO α-DIAZOKETONES

Cyclic α-diazoketones react with phenylsulphenyl chloride at room temperature to furnish α-chloro-α-(phenylthio)cycloalkanones which undergo ready dehydrochlorination to α-(phenylthio)cycloalkenones when treated with triethylamine; acyclic, terminal α-diazoketones also furnish α-chloro-α-(phenylthio)adducts which are useful electrophiles in the synthesis of α-phenyl-α-(phenylthio)ketones.