84010-66-2

Basic information

• Product Name: (R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 84010-66-2
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.21692
• Mol File: 84010-66-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline(84010-66-2)
• EPA Substance Registry System: (R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline(84010-66-2)

Safety Data

• Hazardous Substances Data: 84010-66-2(Hazardous Substances Data)

Usage

General Description

(R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline is a chemical compound that belongs to the class of tetrahydroisoquinolines, which are a group of compounds that possess various pharmacological properties. This particular compound is an enantiomer of 1-methyl-1,2,3,4-tetrahydroisoquinoline, and it has been found to exhibit biological activity in the central nervous system, particularly in relation to dopamine receptors. It has also been studied for its potential neuroprotective and anti-inflammatory properties. Additionally, (R)-1-Methyl-1,2,3,4-tetrahydroisoquinoline has been investigated for its potential use in the treatment of neurodegenerative diseases, such as Parkinson's disease. Overall, this compound is of interest to researchers for its potential therapeutic applications in various neurological and psychiatric conditions.

Upstream product

• 4965-09-7 1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 
• 102922-31-6 (R)-2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline 

Downstream Products

• 178307-42-1 (R)-2-(4-fluoroaniline)-4-(1-methyl-1,2,3,4-tetrahydroisoquinoline-2-yl)-5,6-dimethylpyrimidine hydrochloride 
• 178307-42-1 Revaprazan hydrochloride 

Relevant articles and documents

Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (: R)-2-phenoxypropanoate

The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at -40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.

Catalytic kinetic resolution of cyclic secondary amines

The catalytic resolution of racemic cyclic amines has been achieved by an enantioselective amidation reaction featuring an achiral N-heterocyclic carbene catalyst and a new chiral hydroxamic acid cocatalyst working in concert. The reactions proceed at room temperature, do not generate nonvolatile byproducts, and provide enantioenriched amines by aqueous extraction.