6,7-Dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 6,7-Dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 128942-65-4
• Molecular Formula: C₁₈H₂₁NO₂
• Molecular Weight: 283.37
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID70568425
• Nikkaji Number: J282.799I
• Mol file: 128942-65-4.mol

Synonyms:128942-65-4;6,7-dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline;6,7-DIMETHOXY-2-METHYL-4-PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE;6,7-dimethoxy-2-methyl-4-phenyl-3,4-dihydro-1H-isoquinoline;Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-4-phenyl-;DTXSID70568425;MFCD11501291;AKOS026671882;DS-10383;CS-0151110;J-005636

Chemical Property of 6,7-Dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Melting Point: 79-81 °C
• Boiling Point: 393.4±42.0 °C(Predicted)
• PKA: 7.69±0.40(Predicted)
• PSA: 21.70000
• Density: 1.091±0.06 g/cm3(Predicted)
• LogP: 3.21900
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 283.157228913
• Heavy Atom Count: 21
• Complexity: 329

Purity/Quality:

98% ^*data from raw suppliers

6,7-Dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(C2=CC(=C(C=C2C1)OC)OC)C3=CC=CC=C3

Technology Process of 6,7-Dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

There total 9 articles about 6,7-Dimethoxy-2-methyl-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: 89.0%

2-(N-(3,4-dimethoxybenzyl)-N-methylamino)-1-phenylethyl N',N'-diisopropylcarbamate (1147090-58-1) → 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-4-phenylisoquinoline (55178-75-1,127239-57-0,127306-58-5,128942-65-4)

Guidance literature:

With trifluoroacetic acid; for 44h; Reflux;

DOI:10.1016/j.tet.2009.01.098

Reference yield: 72.0%

1,2-dimethoxybenzene (91-16-7) + 3-methyl-5-phenyloxazolidine (88953-56-4) → 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-4-phenylisoquinoline (55178-75-1,127239-57-0,127306-58-5,128942-65-4)

Guidance literature:

With perchloric acid; In dichloromethane; at -10 - 55 ℃; for 2h;

DOI:10.1021/acs.joc.1c01881

Reference yield: 41.0%

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (16620-96-5) + chlorobenzene (108-90-7) → 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-4-phenylisoquinoline (55178-75-1,127239-57-0,127306-58-5,128942-65-4)

Guidance literature:

2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; With sec.-butyllithium; In diethyl ether; toluene; pentane; at -78 - 0 ℃; for 1h; Inert atmosphere;

chlorobenzene; In diethyl ether; toluene; pentane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol300360r

upstream raw materials:

2-(methyl-veratryl-amino)-1-phenyl-ethanol

2-[(3,4-Dimethoxy-benzyl)-methyl-amino]-1-phenyl-ethanone

N-methylveratrylamine

3,4-dimethoxy-benzaldehyde

Refernces

• 1、 Singh, Kamal Nain,Singh, Paramjit,Singh, Pushpinder,Deol, Yadwinder Singh. "Nucleophilic addition of β-amino carbanions to arynes: One-pot synthesis of 4-aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines". supporting information; experimental part. p. 2202 - 2205. Retrieved 2012/06/18.
• 2、 Venkov, Atanas P.,Vodenicharov, Daniel M.. "A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines". . p. 253 - 255. Retrieved 2007/10/02.