84276-53-9

Upstream product

• 51459-50-8 (4-chlorophenyl)(2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)methanone 
• 135-19-3 β-naphthol 

Relevant academic research and scientific papers

Coupling reaction of 2-hydroxyindoline with arenes by BF3·Et2O. A convenient synthetic method of isolable diasteromeric atropisomers

A simple method for synthesis of 2-aryl-substituted 3,3-dimethylindoline derivatives was established by the reaction of 1-acyl-2-hydroxy-3,3-dimethylindoline with electron-rich arenes in the presence of boron trifluoride-diethylether in dioxane. In the reaction with β-naphthol, a pair of isolable diastereomeric atropisomers was isolated. The conformations of both atropisomers were determined by single crystal X-ray analyses. The substitution reaction behavior toward various arenes was accounted for in terms of frontier molecular orbital (FMO) theory.

Conformation of aromatic rings in isolable atropisomers of 2-arylindoline derivatives and kinetic evidences for π-π interaction

The equilibrium constants [K=anti/syn] of a pair of atropisomers due to restricted rotation about Csp3-Csp2 bond for [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethylindolin-1-yl](4-substituted phenyl)methanone were determined in some solvents. The presence of the effective π-π interaction was demonstrated by the correlation between the equilibrium constants (K) and the substituent effect of the phenyl groups (σp), suggesting that the 'neutral-type' interaction is operative.

Role of 2-naphthyl ether intermediate in formation of isolable atropisomers derived from the coupling reaction of (2-hydroxy-3,3-dimethylindolin-l-yl)-(substituted phenyl)methanones with 2-naphthol

The formation pathway of the atropisomers derived from the reaction of (2-hydroxy-3,3-dimethylindolin-l-yl)(4-substituted phenyl)methanones with 2-naphthol in the presence of BF3·Et2O was discussed on the basis of the isolation of the 2-naphthyl ether intermediate whose structure was determined by single crystal X-ray analysis. The results indicate that the coupling reaction proceeds through stepwise mechanism, i.e., the ether intermediate formation followed by Fries-type rearrangement.

Atropisomers of 1-(acyl or aroyl)-2-naphthylindolines. Isolation, X-ray crystal structure and conformational analysis

A series of pairs of stable diastereomeric atropisomers caused by restricted rotation around the Csp3-Csp2 bond of [2-(2-hydroxynaphthalen-1-yl)- 3,3-dimethyl-2,3-dihydroindol-1-yl]-(3- or 4-substituted phenyl)-methanone or [2-(2-hydroxynaphthalen-1-yl)-3

Crystallographic Analysis of a Pair of Isolable Atropisomers of 2-Aryl Substituted Indoline Derivatives

The cystal and molecular structures of isomeric compounds of 1-(4'-chlorobenzoyl)-2-(2''-hydroxynaphthyl)-3,3-dimethylindoline have been determined by single crystal X-ray analyses as a pair of diastereomeric atropisomers due to restricted rotation about

A CONVENIENT SYNTHETIC METHOD OF 1-ACYL-2-ARYL-3,3-DIMETHYLINDOLINE INVOLVING ISOLABLE DIASTEREOMERIC ATROPISOMERS

The synthesis of 1-acyl-2-aryl-3,3-dimethylindoline was improved by the reaction of 1-acyl-2-hydroxy-3,3-dimethylindoline with an arene in the presence of BF3*O(C2H5)2 in dioxane, and stable diastereomeric atropisomers were isolated as products when the a

HINDERED ROTATION IN 2-ARYLINDOLINES. ISOLATION OF DIASTEREOMERIC ATROPISOMERS

The condensation reaction of 1-(p-chlorobenzoyl)-2-hydroxy-3,3-dimethylindoline with β-naphthol gave a pair of diastereomeric atropisomers due to restricted rotation about an sp3 - sp2 carbon bond.