66948-16-1

Basic information

• Product Name: rac-2-(isoquinolin-1-yl)-1-phenylethan-2-ol
• Synonyms: rac-2-(isoquinolin-1-yl)-1-phenylethan-2-ol
• CAS NO: 66948-16-1
• Molecular Weight: 249.312
• Mol File: 66948-16-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: rac-2-(isoquinolin-1-yl)-1-phenylethan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: rac-2-(isoquinolin-1-yl)-1-phenylethan-2-ol(66948-16-1)
• EPA Substance Registry System: rac-2-(isoquinolin-1-yl)-1-phenylethan-2-ol(66948-16-1)

Safety Data

• Hazardous Substances Data: 66948-16-1(Hazardous Substances Data)

Upstream product

• 1721-93-3 1-methylisoquinoline 
• 100-52-7 benzaldehyde 
• 27104-72-9 methyl isoquinoline-1-carboxylate 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 27311-63-3 1-Hydroxymethyl-isoquinoline 
• 27039-28-7 1-(acetoxymethyl)-isoquinoline 

Downstream Products

• 1126532-65-7 (S)-2-(isoquinolin-1-yl)-1-phenylethanol 
• 1007107-28-9 (R)-2-isoquinolin-1-yl-1-phenylethanol 
• 1227475-50-4 (S)-1-(2-(bis(3,5-dimethylphenyl)(methyl)silyloxy)-2-phenylethyl)isoquinoline 
• 1126532-47-5 (^SiR,R)-1-[2-(1-tert-butyl-1-silatetralinyl-1-oxy)-2-phenylethyl]isoquinoline 
• 1007107-20-1 C₃₀H₃₃NOSi 

Relevant articles and documents

Stereoselective alcohol silylation by dehydrogenative Si-O coupling: Scope, limitations, and mechanism of the Cu-H-catalyzed non-enzymatic kinetic resolution with silicon-stereogenic silanes

Ligand-stabilized copper(I)hydride catalyzes the dehydrogenative Si-O coupling of alcohols and silanes-a process that was found to proceed without racemization at the silicon atom if asymmetrically substituted. The present investigation starts from this pivotal observation since silicon-stereogenic silanes are thereby suitable for the reagent-controlled kinetic resolution of racemic alcohols, in which asymmetry at the silicon atom enables discrimination of enantiomeric alcohols. In this full account, we summarizeour efforts to systematically examine this unusual strategy of diastereoselective alcohol silylation. Ligand (sufficient reactivity with moderately electron-rich monophosphines), silane (reasonable diastereocontrol with cyclic silanes having a distinct substitution pattern) as well as substrate identification (chelating donor as a requirement) areintroductorily described. With these basic data at hand, the substrate scope was defined employing enantiomerically enriched tert-butyl-substituted 1-silatetraline and highly reactive 1-si-laindane. The synthetic part is complemented by the determination of the stereochemical course at the silicon atom in the Si-O coupling step followed by its quantum-chemical analysis thus providing a solid mechanistic picture of this remarkable transformation.

AN ALDOL-TYPE REACTION OF ACTIVE METHYL GROUPS OF NITROGEN-CONTAINING HETEROAROMATIC COMPOUNDS

Active methyl groups of nitrogen-containing heteroaromatic compounds react with benzaldehydes in the presence of 9-BBN triflate and diisopropylethylamine in dichloromethane to give the corresponding aldol-type products under mild conditions.