6-Methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 6-Methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 54893-54-8
• Molecular Formula: C11H15NO
• Molecular Weight: 177.2429
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID50203382
• Nikkaji Number: J690.644C
• Wikidata: Q83076756
• ChEMBL ID: CHEMBL4075463
• Mol file: 54893-54-8.mol

Synonyms:6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline;54893-54-8;6-methoxy-2-methyl-3,4-dihydro-1H-isoquinoline;1,2,3,4-Tetrahydro-6-methoxy-2-methylisoquinoline;BRN 0132986;CHEMBL4075463;ISOQUINOLINE, 1,2,3,4-TETRAHYDRO-6-METHOXY-2-METHYL-;5-21-02-00327 (Beilstein Handbook Reference);SCHEMBL14340583;DTXSID50203382;AMY16209;BDBM50270375;MFCD01717130;AKOS025149795;LS-85990;CS-0453656;F14520;A913937;1,2,3,4-Tetrahydro-2-methyl-6-methoxyisoquinoline

Chemical Property of 6-Methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Vapor Pressure: 0.00831mmHg at 25°C
• Boiling Point: 267.1°Cat760mmHg
• PKA: 8.55±0.20(Predicted)
• Flash Point: 78.4°C
• PSA: 12.47000
• Density: 1.034g/cm³
• LogP: 1.62100
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 177.115364102
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

98.5% ^*data from raw suppliers

6-Methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=C(C1)C=CC(=C2)OC

Technology Process of 6-Methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

There total 23 articles about 6-Methoxy-2-methyl-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: 87.0%

6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde (212188-99-3) → 6‐methoxy‐N‐methyl‐1,2,3,4‐tetrahydroisoquinoline (54893-54-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1248/cpb.46.918

Reference yield: 80.0%

6-methoxy-2-methylisoquinolin-2-ium iodide → 6‐methoxy‐N‐methyl‐1,2,3,4‐tetrahydroisoquinoline (54893-54-8)

Guidance literature:

With hydrogen; platinum; In ethanol; at 20 ℃; for 6h;

DOI:10.1016/0006-2952(95)02086-1

Reference yield: 31.0%

6-methoxy-1,2,3,4-tetrahydro-isoquinoline (42923-77-3) + S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) → 6‐methoxy‐N‐methyl‐1,2,3,4‐tetrahydroisoquinoline (54893-54-8)

Guidance literature:

With coclaurine N-methyltransferase cross‐linked enzyme aggregates; In aq. phosphate buffer; water; at 20 ℃; for 24h; pH=7; Enzymatic reaction;

DOI:10.1002/anie.201805060

upstream raw materials:

formaldehyd

2-(3-methoxyphenyl)-N-methylethan-1-amine

6-methoxy-1,2,3,4-tetrahydro-isoquinoline

6-methoxy-2-methyl-3,4-dihydro-isoquinolinium; iodide

Downstream raw materials:

N-methyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline

6-methoxy-4-(3-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

6-methoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Bennett, Matthew R.,Thompson, Mark L.,Shepherd, Sarah A.,Dunstan, Mark S.,Herbert, Abigail J.,Smith, Duncan R. M.,Cronin, Victoria A.,Menon, Binuraj R. K.,Levy, Colin,Micklefield, Jason. "Structure and Biocatalytic Scope of Coclaurine N-Methyltransferase". supporting information. p. 10600 - 10604. Retrieved 2018/08/17.
• 2、 Shinohara, Tatsumi,Takeda, Akira,Toda, Jun,Ueda, Yoko,Kohno, Michiyo,Sano, Takehiro. "A synthesis of mono- and dimethoxy-1,2,3,4-tetrahydroisoquinolines via Pummerer reaction: Effects of methoxyl groups on intramolecular cyclization". . p. 918 - 927. Retrieved 2007/10/03.