1,2-methylenedioxy-6a,7-dehydronoraporphine

Base Information

• Chemical Name: 1,2-methylenedioxy-6a,7-dehydronoraporphine
• CAS No.: 41679-82-7
• Molecular Formula: C₁₇H₁₃NO₂
• Molecular Weight: 263.296

Synonyms:

Chemical Property of 1,2-methylenedioxy-6a,7-dehydronoraporphine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

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Technology Process of 1,2-methylenedioxy-6a,7-dehydronoraporphine

There total 1 articles about 1,2-methylenedioxy-6a,7-dehydronoraporphine 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:

7-Chloro-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline → liriodenine (475-75-2) + 1,2-methylenedioxy-6a,7-dehydronoraporphine (41679-82-7) + 7-chloro-6a,7-dehydroanonaine + (+/-)-7,7'-bis-6a,7-dehydroanonaine

Guidance literature:

With sodium ethanolate; In ethanol; at 70 ℃; for 0.166667h; Yield given. Yields of byproduct given;

Reference yield: 76.0%

1,2-methylenedioxy-6a,7-dehydronoraporphine (41679-82-7) → duguenaine (80550-24-9)

Guidance literature:

With formaldehyd; In water; for 24h; Ambient temperature;

Reference yield: 30.0%

1,2-methylenedioxy-6a,7-dehydronoraporphine (41679-82-7) → liriodenine (475-75-2) + (+/-)-7,7'-bis-6a,7-dehydroanonaine

Guidance literature:

With air; In methanol; dichloromethane; for 240h; Ambient temperature;

Downstream raw materials:

liriodenine

duguenaine

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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