64982-61-2

Basic information

• Product Name: (S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline
• Synonyms: (S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline;(S)-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride(WXC08459S1)
• CAS NO: 64982-61-2
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.21692
• Mol File: 64982-61-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: (S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline(64982-61-2)
• EPA Substance Registry System: (S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline(64982-61-2)

Safety Data

• Hazardous Substances Data: 64982-61-2(Hazardous Substances Data)

Usage

General Description

(S)-1-Methyl-1,2,3,4-tetrahydro-isoquinoline is a chemical compound belonging to the class of tetrahydroisoquinolines, which are commonly found in various natural products such as alkaloids and pharmaceutical compounds. This specific compound is a chiral molecule with a methyl group attached to the first carbon of the tetrahydroisoquinoline ring. It is used in research and pharmaceutical applications due to its potential pharmacological properties, including its role as a dopamine receptor antagonist and its ability to interact with the central nervous system. Additionally, it has been investigated for its potential neuroprotective and antioxidant effects, making it of interest for the development of novel drugs targeting neurological disorders.

Upstream product

• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 
• 4965-09-7 1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 487-68-3 mesytaldehyde 
• 102922-31-6 (R)-2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline 

Downstream Products

• 1346681-97-7 benzyl (1R)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 178307-42-1 Revaprazan hydrochloride 
• 1721-93-3 1-methylisoquinoline 
• 4965-09-7 1-methyl-1,2,3,4-tetrahydroisoquinoline 

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.

Chiral Dipole-Stabilized Anions: Experiment and Theory in Benzylic and Allylic Systems. Stereoselective Deprotonations, Pyramidal Inversions, and Stereoselective Alkylations of Lithiated (Tetrahydroisoquinolyl)oxazolines

The stereoselective alkylation of chiral (tetrahydroisoquinolyl)oxazolines has been investigated.We report the details of this investigation, including an examination of the effect of both temperature and oxazoline substituent structure on the alkylation diastereoselectivity, a comparison of monodentate vs bidentate chelation of the organolithium, an evaluation of the effect of solvent and chelating solvent additives, the regiochemistry of alkylation of (3,4-dehydropiperidino)oxazolines, lithiation-alkylation experiments on stereoselectively deuterated monodentate and bidentate isoquinolinolyloxazolines, and semiempirical molecular orbital calculations on the organolithium diastereomers 13a,b.There are two distinct stereoselective processes involved in the overall transformation. the proposed mechanism includes an oxazoline-alkyllithium coordination complex that controls the selectivity of the deprotonation step, whereas the selectivity of the electrophilic quench is governed by effects that are as yet undetermined.