Cepharadione B

Base Information

• Chemical Name: Cepharadione B
• CAS No.: 55610-02-1
• Molecular Formula: C19H15NO4
• Molecular Weight: 321.3267
• UNII: 47F7X76GJ6
• DSSTox Substance ID: DTXSID70204159
• Nikkaji Number: J11.855I
• Wikidata: Q83077598
• Metabolomics Workbench ID: 44368
• ChEMBL ID: CHEMBL396085
• Mol file: 55610-02-1.mol

Synonyms:cepharadione B

Chemical Property of Cepharadione B

Chemical Property:

• Vapor Pressure: 3.53E-13mmHg at 25°C
• Boiling Point: 573.9°Cat760mmHg
• Flash Point: 300.9°C
• PSA: 57.53000
• Density: 1.345g/cm³
• LogP: 2.66010
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 321.10010796
• Heavy Atom Count: 24
• Complexity: 536

Purity/Quality:

98.0% ^*data from raw suppliers

CepharadioneB ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C2=CC3=CC=CC=C3C4=C2C(=CC(=C4OC)OC)C(=O)C1=O
• General Description: 1,2-Dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-4,5(6H)-dione (cepharadione B) is an aporphinoid alkaloid synthesized via an intermolecular benzyne cycloaddition (IBC) approach, demonstrating the efficiency and selectivity of this method for constructing complex isoquinoline structures. The compound is part of a broader class of pharmacologically relevant alkaloids, and its synthesis highlights the versatility of the IBC strategy in accessing structurally diverse aporphinoids.

Technology Process of Cepharadione B

There total 10 articles about Cepharadione B 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: 65.0%

oxalyl dichloride (79-37-8) + 2-(2',3'-dimethoxybiphenyl-2-yl)-N-methylacetamide (185985-94-8) → cepharadione B (55610-02-1)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 60 ℃; for 24h;

DOI:10.1016/j.tet.2004.05.014

Reference yield: 65.0%

norcepharadione B (57576-41-7) + methyl trifluoromethanesulfonate (333-27-7) → cepharadione B (55610-02-1)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; for 2h;

DOI:10.1021/jo00009a010

Reference yield: 65.0%

Methyl fluorosulfonate (421-20-5) + norcepharadione B (57576-41-7) → cepharadione B (55610-02-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)86859-8

upstream raw materials:

Methyl fluorosulfonate

norcepharadione B

methyl trifluoromethanesulfonate

2-Chloro-N-(5,6-dimethoxy-phenanthren-9-yl)-N-methyl-acetamide

Downstream raw materials:

dehydronuciferine

Refernces

Intermolecular Benzyne Cycloaddition Approach to Aporphinoids. Total Syntheses of Norcepharadione B, Cepharadione B, Dehydroanonaine, Duguenaine, Dehydronornuciferine, Pontevedrine, O-Methylatheroline, Lysicamine, and Alkaloid PO-3

10.1021/jo00009a010

The research focuses on the development of a novel approach to the synthesis of aporphinoids, a class of isoquinoline alkaloids with potential pharmacological properties. The purpose of the study was to create a more efficient method for synthesizing these complex compounds, particularly dehydroaporphines, aristolactams, and other related structures, through intermolecular benzyne cycloaddition (IBC). The researchers successfully reported the total synthesis of several isoquinoline alkaloids, including norcepharadione B, cepharadione B, dehydroanonaine, duguenaine, dehydronornuciferine, pontevedrine, 0-methylatheroline, lysicamine, and alkaloid PO-3. The study concluded that the IBC approach was highly selective and efficient, allowing for the synthesis of aporphinoids with no ring-D substituents in yields of up to 50%. Key chemicals used in the process included 1-methyleneisoquinolines, arynes, and various benzenediazonium-2-carboxylates, which served as benzyne precursors in the cycloaddition reactions. The research also explored the synthesis of aporphinoids with ring-D substituents using alkoxy-substituted benzynes and unsymmetrically substituted benzynes, demonstrating the versatility of the IBC method.