4-Phenyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 4-Phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 75626-12-9
• Molecular Formula: C15H15N
• Molecular Weight: 209.291
• Hs Code.: 2933499090
• European Community (EC) Number: 828-961-9
• ChEMBL ID: CHEMBL283130
• Nikkaji Number: J523.682G
• Wikidata: Q27190592
• Mol file: 75626-12-9.mol

Synonyms:4-phenyl-1,2,3,4-tetrahydroisoquinoline;4PTIQ

Chemical Property of 4-Phenyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Vapor Pressure: 5.62E-06mmHg at 25°C
• Boiling Point: 344 °C at 760 mmHg
• Flash Point: 171.2 °C
• PSA: 12.03000
• Density: 1.065 g/cm³
• LogP: 4.05250
• Storage Temp.: Store at RT
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 209.120449483
• Heavy Atom Count: 16
• Complexity: 220

Purity/Quality:

97% ^*data from raw suppliers

4-Phenyl-1,2,3,4-tetrahydroisoquinoline Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2=CC=CC=C2CN1)C3=CC=CC=C3
• Uses: An inhibitor of release of dopamine induced by methamphetamine 4-Phenyl-1,2,3,4-tetrahydroisoquinoline is a deaminated and demethylated nomifensine analog methamphetamine induced dopamine release inhibitor.

Technology Process of 4-Phenyl-1,2,3,4-tetrahydroisoquinoline

There total 24 articles about 4-Phenyl-1,2,3,4-tetrahydroisoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

2-benzylamino-1-phenyl-ethanol (51096-49-2,91579-12-3,107171-75-5,27159-30-4) → 4-phenyl-1,2,3,4-tetrahydroisoquinoline (75626-12-9)

Guidance literature:

With trifluorormethanesulfonic acid; for 3h; Ambient temperature;

DOI:10.1248/cpb.43.1543

Reference yield: 83.0%

3,4-dihydro-4-phenylisoquinoline (6187-58-2) → 4-phenyl-1,2,3,4-tetrahydroisoquinoline (75626-12-9)

Guidance literature:

With bis(trifluoroacetoxy)borane-tetrahydrofuran; In tetrahydrofuran; trifluoroacetic acid; at 0 - 5 ℃; for 0.0166667h;

DOI:10.1021/jo00315a025

Reference yield: 72.0%

2-(methylsulfonyl)-4-phenyl-1,2-dihydroisoquinolin-3(4H)-one → 4-phenyl-1,2,3,4-tetrahydroisoquinoline (75626-12-9)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; diborane; In toluene; at 110 ℃; for 1h; Reflux;

DOI:10.1002/anie.201502553

upstream raw materials:

4-phenylisoquinoline

3,4-dihydro-4-phenylisoquinoline

2-benzylamino-1-phenyl-ethanol

2-(o-acetylaminobenzyl)-4-phenyl-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

((S)-1-tert-Butoxymethyl-2-methyl-propyl)-[1-(4-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-amine

3,4-dihydro-4-phenylisoquinoline

(4R)-(+)-4-phenyl-1,2,3,4-tetrahydroisoquinoline

(4S)-(-)-4-phenyl-1,2,3,4-tetrahydroisoquinoline

Refernces

A CONVENIENT ASYMMETRIC SYNTHESIS OF PYRROLO<2,1-a>ISOQUINOLINES

10.1016/0040-4039(90)80155-F

The research focuses on the asymmetric synthesis of pyrrolo[2,1-a]isoquinolines, a class of compounds with significant anti-depressant activity. The purpose of the study was to develop a convenient and efficient four-step synthesis method for optically pure Ga-phenyl pyrroloisoquinolines starting from chiral formamidines. The process involved metalation with s-BuLi or t-BuLi at -78°C, followed by alkylation with 1-chloro-3-iodopropane at -100°C, and removal of the formamidine auxiliary to produce the secondary amine, which spontaneously cyclized to form the desired compounds. The method was found to be effective, yielding the products in good yield and high optical purity. Key chemicals used in the process included 4-phenyl-1,2,3,4-tetrahydroisoquinoline, dimethylaminoformamidine, P-methyl-1-methoxypropyl amine, and 1-chloro-3-iodopropane, among others.

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