Corypalline

Base Information

• Chemical Name: Corypalline
• CAS No.: 450-14-6
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• Hs Code.: 2933499090
• NSC Number: 131674
• DSSTox Substance ID: DTXSID60299630
• Nikkaji Number: J11.374C
• Wikidata: Q82042126
• Metabolomics Workbench ID: 143215
• ChEMBL ID: CHEMBL593001
• Mol file: 450-14-6.mol

Synonyms:Corypalline;450-14-6;6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol;CHEMBL593001;6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol;NSC131674;SCHEMBL20683185;DTXSID60299630;FELOSQQXIHRUSH-UHFFFAOYSA-N;BDBM50006640;NSC-131674;CS-0530330;2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline

Chemical Property of Corypalline

Chemical Property:

• Vapor Pressure: 0.000161mmHg at 25°C
• Refractive Index: 1.564
• Boiling Point: 321.2 °C at 760 mmHg
• Flash Point: 148.1 °C
• PSA: 32.70000
• Density: 1.138 g/cm³
• LogP: 1.32660
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 198

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1)O)OC

Technology Process of Corypalline

There total 8 articles about Corypalline 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: 18.3%

2.6-dimethylphenol (576-26-1,25134-01-4) + p-quinol acetate (19373-80-9) → 6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol (450-14-6) + 7-(4-hydroxy-3,5-dimethylphenoxy)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline + 7-hydroxy-6-methoxy-8-(4-hydroxy-3,5-dimethylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1248/cpb.36.1627

Reference yield:

(+/-)-orientaline (20938-53-8) → 1,2-didehydrocoripallinium ion (72142-82-6) + 6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol (450-14-6) + 4-hydroxymethyl-2-methoxyphenol (498-00-0) + 2,9-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,10,11-triol

Guidance literature:

With dihydrogen peroxide; In methanol; water; for 14h; Ambient temperature; ascorbate oxidase from Cucurbita pepo medullosa L_., phosphate buffer pH 7.0;

Reference yield:

N-methylcoclaurine (1472-62-4) → N-methylcrotsparine (17127-48-9) + 6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol (450-14-6) + (4-hydroxyphenyl)methanol (623-05-2) + 2-Methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,10,11-triol (72142-83-7)

Guidance literature:

With dihydrogen peroxide; In methanol; water; for 14h; Further byproducts given; Ambient temperature; ascorbate oxidase from Cucurbita pepo medullosa L_., phosphate buffer pH 7.0;

upstream raw materials:

2.6-dimethylphenol

p-quinol acetate

(+/-)-orientaline

(+/-)-6-hydroxy-7-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

7-acetoxy-6-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

o-acetyl-1-phenylcorypalline

O,O'-diacetyl-8,8'-bicorypallyl

6-methoxy-2-methyl-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol

Refernces

• 1、 Hara,Murakata,Hoshino,Umezawa,Iitaka. "Studies on tetrahydroisoquinolines. XXX. A synthesis of mixed tetrahydroisoquinoline dimers via p-quinol acetates". . p. 1627 - 1637. Retrieved 2007/10/02.
• 2、 Irie, Hiroshi,Shiina, Ayako,Fushimi, Tamaki,Katakawa, Jun'ichi,Fujii, Nobutaka,Yajima, Haruaki. "NEW SYNTHESIS OF ISOQUINOLINE ALKALOIDS, THALIFOLINE, CORYPALLINE, AND CHERYLLINE". . p. 875 - 878. Retrieved 2007/10/02.