cas 56293-29-9, ALOPERINE | Articles data ｜lookchem

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56293-29-9

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Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine
The enantioselective synthesis of the lupinine alkaloid (+)-aloperine is described. The synthetic scheme presents three steps that are mediated by enzymes: kinetic resolution, oxidation of a primary alcohol to an aldehyde and oxidation of a secondary alco
Barilli, Alessio,Belinghieri, Francesca,Passarella, Daniele,Lesma, Giordano,Riva, Sergio,Silvani, Alessandra,Danieli, Bruno
p. 2921 - 2925
(2007/10/03)

Total synthesis of (+)-aloperine. Use of a nitrogen-bound silicon tether in an intramolecular diels-alder reaction
Enantioselective total syntheses of aloperine (1), N-methylaloperine (2), and N-allylaloperine (3) are reported. The central element of the synthetic strategy is an intramolecular Diels-Alder reaction in which the cycloaddends are tethered by a N-silylamine linkage. The total synthesis of 1 proceeds from commercially available 3-hydroxypiperidine hydrochloride (54) and (R)-pipecolinic acid (35) by way of nine isolated and purified intermediates. The synthesis is sufficiently efficient that gram quantities of (+)-aloperine (1) can be readily prepared. Early exploratory studies also introduced a convenient method for tethering cycloaddition partners with a sulfonamide unit to realize the intramolecular Diels-Alder cycloaddition of a vinylsulfonamide: 45 → 46.
Brosius, Arthur D.,Overman, Larry E.,Schwink, Lothar
p. 700 - 709
(2007/10/03)

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Chemical Properties

Appearance/Colour :yellow crystalline powder
Melting Point: 67-72 °C
Boiling Point: 367.7 °C at 760 mmHg
Flash Point:155.8 °C
Density: 1.1g/cm³
Storage Temp.:Keep in dark place,Inert atmosphere,Room temperature
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.583
PKA: 10.31±0.20(Predicted)
PSA: 15.27000
LogP: 2.43570

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