Norcepharadione B

Base Information

• Chemical Name: Norcepharadione B
• CAS No.: 57576-41-7
• Molecular Formula: C18H13NO4
• Molecular Weight: 307.30
• Mol file: 57576-41-7.mol

Synonyms:4H-Dibenzo[de,g]quinoline-4,5(6H)-dione,1,2- dimethoxy-;

Chemical Property of Norcepharadione B

Chemical Property:

• Refractive Index: 1.699
• PSA: 68.39000
• Density: 1.373 g/cm³
• LogP: 2.64970

Purity/Quality:

98%min ^*data from raw suppliers

NorcepharadioneB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Norcepharadione B is a dibenzoquinoline-derived alkaloid characterized by a 4H-dibenzo[de,g]quinoline-4,5(6H)-dione core structure with 1,2-dimethoxy substitutions. It belongs to the aporphinoid class and was synthesized via an intermolecular benzyne cycloaddition (IBC) approach, demonstrating the method's efficiency in constructing complex isoquinoline alkaloids without ring-D substituents.

Technology Process of Norcepharadione B

There total 2 articles about Norcepharadione 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: 62.0%

1,2,3,4-tetrahydro-1,6,7-trimethoxy-1-methylisoquinoline-3,4-dione (82359-80-6) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → norcepharadione B (57576-41-7)

Guidance literature:

With isopentyl nitrite; trichloroacetic acid; In 1,2-dimethoxyethane; Heating;

DOI:10.1021/jo00009a010

Reference yield:

6,7-Dimethoxy-1-methylene-1,2-dihydro-isoquinoline-3,4-dione (82359-79-3) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → norcepharadione B (57576-41-7)

Guidance literature:

With isopentyl nitrite; trichloroacetic acid; In 1,2-dimethoxyethane; for 7h; Heating;

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

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

upstream raw materials:

6,7-Dimethoxy-1-methylene-1,2-dihydro-isoquinoline-3,4-dione

anthranilic acid

1,2,3,4-tetrahydro-1,6,7-trimethoxy-1-methylisoquinoline-3,4-dione

Downstream raw materials:

cepharadione B

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.

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