Cherylline

Base Information

• Chemical Name: Cherylline
• CAS No.: 23367-61-5
• Deprecated CAS: 612483-14-4
• Molecular Formula: C17H19 N O3
• Molecular Weight: 285.3377
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID40177922
• Nikkaji Number: J16.304J
• Wikidata: Q27114300
• Metabolomics Workbench ID: 67976
• Mol file: 23367-61-5.mol

Synonyms:cherylline

Chemical Property of Cherylline

Chemical Property:

• Vapor Pressure: 3.71E-09mmHg at 25°C
• Boiling Point: 462°Cat760mmHg
• Flash Point: 233.2°C
• PSA: 52.93000
• Density: 1.227g/cm³
• LogP: 2.62160
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 285.13649347
• Heavy Atom Count: 21
• Complexity: 343

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(C2=CC(=C(C=C2C1)O)OC)C3=CC=C(C=C3)O
• Isomeric SMILES: CN1C[C@H](C2=CC(=C(C=C2C1)O)OC)C3=CC=C(C=C3)O
• Uses: Cherylline is a 4-arylisoquinoline derivative, a group with several potential medicinal properties, including a weak acetylcholinesterase inhibitory activity. Mesembrenone, in turn, is mildly active against Molt 4 lymphoid and non-tumoral fibroblastic LMTK cells, has a moderate hypotensive effect on arterial pressure, and interacts slightly with DNA.

Technology Process of Cherylline

There total 10 articles about Cherylline 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: 96.0%

(S)-7-(benzyloxy)-4-(4-(benzyloxy)phenyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (96444-12-1) → (4S)-4-(4-hydroxyphenyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol (23367-61-5)

Guidance literature:

With hydrogenchloride; In ethanol;

DOI:10.1039/c39840001646

Reference yield: 90.0%

(4S)-5-hydroxymethyl-4-[1-(4-hydroxyphenyl)-2-methylaminoethyl]-2-methoxyphenol (612483-13-3) → (4S)-4-(4-hydroxyphenyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol (23367-61-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; toluene; for 9h; Heating;

DOI:10.1039/b302168h

Reference yield:

(1S,1'R)-5-benzyloxy-2-{1-(4-benzyloxyphenyl)-2-[methyl-(1'-phenylethyl)amino]ethyl}-4-methoxybenzaldehyde (612483-12-2) → (4S)-4-(4-hydroxyphenyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol (23367-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / H₂ / 10 percent Pd/C / methanol / 24 h / 20 °C

2: 90 percent / p-TsOH / toluene; methanol / 9 h / Heating

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; toluene;

DOI:10.1039/b302168h

upstream raw materials:

(S)-7-(benzyloxy)-4-(4-(benzyloxy)phenyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

(4S)-5-hydroxymethyl-4-[1-(4-hydroxyphenyl)-2-methylaminoethyl]-2-methoxyphenol

(1S,1'R)-5-benzyloxy-2-{1-(4-benzyloxyphenyl)-2-[methyl-(1'-phenylethyl)amino]ethyl}-4-methoxybenzaldehyde

(S)-3,9-Bis-benzyloxy-2-methoxy-7,12-dihydro-5H-6,12-methano-dibenzo[c,f]azocine 6-oxide

Downstream raw materials:

(S)-6,7-dimethoxy-4-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline