Pseudopalmatine

Base Information

• Chemical Name: Pseudopalmatine
• CAS No.: 19716-66-6
• Molecular Formula: C21H22 N O4
• Molecular Weight: 352.40368
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30349252
• Nikkaji Number: J413.908I
• Wikidata: Q27138980
• Metabolomics Workbench ID: 133145
• ChEMBL ID: CHEMBL376300
• Mol file: 19716-66-6.mol

Synonyms:pseudopalmatine

Chemical Property of Pseudopalmatine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 40.80000
• Density: g/cm³
• LogP: 3.38480
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 352.15488318
• Heavy Atom Count: 26
• Complexity: 475

Purity/Quality:

98.0% Min., ^*data from raw suppliers

Pseudopalmatine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)CC[N+]3=CC4=CC(=C(C=C4C=C23)OC)OC)OC

Technology Process of Pseudopalmatine

There total 12 articles about Pseudopalmatine 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: 49.0%

potassium cyanide (151-50-8) + (+/-)-trans-xylopinine N-oxide (75821-47-5) → pseudopalmatine (19716-66-6) + (8S,14S)-(+/-)-8-cyanoxylopinine

Guidance literature:

(+/-)-trans-xylopinine N-oxide; With trifluoroacetic anhydride; In dichloromethane; at -30 - 20 ℃;

potassium cyanide; With sodium acetate; In dichloromethane; water; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)00945-5

Reference yield:

2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline (26067-60-7) → pseudopalmatine (19716-66-6)

Guidance literature:

With iodine; potassium acetate; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201601245

Reference yield:

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5,66820-84-6) → pseudopalmatine (19716-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂O / Heating

2.1: 55 percent / mCPBA / CHCl₃ / 20 °C

3.1: TFAA / CH₂Cl₂ / -30 - 20 °C

3.2: NaOAc / CH₂Cl₂; H₂O / 0.5 h / 20 °C

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In dichloromethane; chloroform; water; 1.1: Cyclization / 2.1: Oxidation / 3.1: Elimination / 3.2: Addition;

DOI:10.1016/S0040-4020(00)00945-5

upstream raw materials:

potassium cyanide

(+/-)-trans-xylopinine N-oxide

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride

2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline

Refernces

• 1、 Suau, Rafael,Nájera, Francisco,Rico, Rodrigo. "The Polonovski-Potier reaction of berbine N-oxides. Synthesis of 8-hydroxymethyl and 8-methylberbines". . p. 9713 - 9723. Retrieved 2007/10/03.