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482-28-0

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ORGANOMETALLIC REAGENTS IN SYNTHESIS A NEW PROTOCOL FOR CONSTRUCTION OF THE INDOLE NUCLEUS
Organodilithium reagents derived from 2-alkyl-N-trimethylsilyl anilines undergo condensation with esters of carboxylic acids to afford substituted indoles.A total of 16 examples are reported; yields in general were good.In conjuction with this program, a convenient, large-scale procedure for preparation of monosilylated anilines was also developed.To demonstrate the utility of the new indole protocol in natural products synthesis, efficient syntheses of (+)-cinchonamine and (+)-epi-cinchonamine as well as a tetracyclic model system for the architecturally complex penitrem mycotoxins were completed in regio- and stereoselective fashion.
Smith, III, Amos B.,Visnick, Melean,Haseltine, John N.,Sprengeler, Paul A.
p. 2957 - 2970
(2007/10/02)

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Chemical Properties

Melting Point: 186°; mp 194°
Boiling Point: 477.9°Cat760mmHg
Flash Point:242.8°C
Density: 1.2g/cm³
Vapor Pressure: 6.11E-10mmHg at 25°C
Refractive Index: 1.5600 (estimate)
PKA: pK in 80% methyl Cellosolve: 8.28(at 25℃)
PSA: 39.26000
LogP: 3.20950

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