189288-86-6

Basic information

• Product Name: (3Z,4R)-1-benzyl-3-ethylidene-4-(2-indolylmethyl)piperidine
• CAS NO: 189288-86-6
• Molecular Weight: 330.473
• Mol File: 189288-86-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3Z,4R)-1-benzyl-3-ethylidene-4-(2-indolylmethyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (3Z,4R)-1-benzyl-3-ethylidene-4-(2-indolylmethyl)piperidine(189288-86-6)
• EPA Substance Registry System: (3Z,4R)-1-benzyl-3-ethylidene-4-(2-indolylmethyl)piperidine(189288-86-6)

Safety Data

• Hazardous Substances Data: 189288-86-6(Hazardous Substances Data)

Upstream product

• 82185-43-1 N-(trimethylsilyl)-o-toluidine 
• 189288-85-5 [(R)-1-Benzyl-3-eth-(Z)-ylidene-piperidin-4-yl]-acetic acid methyl ester 
• 100-44-7 benzyl chloride 
• 72504-66-6 (1R)-1-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)ethanol 

Downstream Products

• 189288-87-7 (1S,4aR,11R,11aS)-2-Benzyl-1-cyano-11-methyl-1,2,3,4,4a,5,11,11a-octahydro-pyrido[4,3-b]carbazole-6-carboxylic acid tert-butyl ester 

Relevant articles and documents

Total syntheses of the Strychnos indole alkaloids (-)-tubifoline, (-)-tubifolidine, and (-)-19,20-dihydroakuammicine

Two different strategies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of 1-(3-pyridyl)ethanol, followed by partial reduction of the pyridine ring to the tetrahydropyridine level, Claisen rearrangement of the resulting allylic alcohol, and finally Smith indolization. Whereas 2-(4-piperidylmethyl)indole 6 could not be converted to tetracyclic ABDE substructures of Strychnas alkaloids, photocyclization of chloroacetamide 14, derived from (piperidylmethyl)indole 13, satisfactorily afforded the stemmadenine-type tetracycle 15, which was then converted to the alkaloids (-)-tubifoline, (-)-tubifolidine, and (-19,20-dihydroakuammicine.