Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizinium, 6,7-dihydro-13-methyl-

Base Information

• Chemical Name: Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizinium, 6,7-dihydro-13-methyl-
• CAS No.: 30243-28-8
• Molecular Formula: C₂₀H₁₆NO₄
• Molecular Weight: 334.351
• DSSTox Substance ID: DTXSID00184339
• Nikkaji Number: J259.987B
• ChEMBL ID: CHEMBL3558290
• Mol file: 30243-28-8.mol

Synonyms:Corysamine;13-Methylcoptisine;Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizinium, 6,7-dihydro-13-methyl-;Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium, 6,7-dihydro-13-methyl-;CHEMBL3558290;C20H16NO4;DTXSID00184339;C20-H16-N-O4;FT-0701570

Chemical Property of Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizinium, 6,7-dihydro-13-methyl-

Chemical Property:

• Melting Point: >300 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 40.80000
• Density: g/cm³
• LogP: -0.01510
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 334.10793299
• Heavy Atom Count: 25
• Complexity: 530

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC3=C(C2=C[N+]4=C1C5=CC6=C(C=C5CC4)OCO6)OCO3

Technology Process of Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizinium, 6,7-dihydro-13-methyl-

There total 6 articles about Bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizinium, 6,7-dihydro-13-methyl- 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: 95.0%

(+/-)-tetrahydrocorysamine (19775-54-3,32043-26-8,41607-17-4,42511-93-3,42511-94-4) → corysamine (30243-28-8)

Guidance literature:

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

DOI:10.1002/chem.201601245

Reference yield: 57.0%

C20H17NO4 → corysamine (30243-28-8)

Guidance literature:

With rhodium(III) chloride trihydrate; oxygen; In ethanol; at 80 ℃; for 8h;

DOI:10.1002/chem.201601245

Reference yield:

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline (94143-83-6) → corysamine (30243-28-8)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve

2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere

3: sodium formate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere

4: rhodium(III) chloride trihydrate; oxygen / ethanol / 8 h / 80 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; rhodium(III) chloride trihydrate; oxygen; sodium formate; potassium carbonate; benzoic acid; In methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.201601245

upstream raw materials:

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

5-bromo-benzo[1,3]dioxole-4-carbaldehyde

(+/-)-tetrahydrocorysamine

Downstream raw materials:

(+/-)-acetylisocorynolide

(+/-)-acetylcorynoline

(+/-)-11-epicorynoline

Refernces

A BIOMIMETIC SYNTHESIS OF <+/->-CORYNOLINE, <+/->-11-EPICORYNOLINE, <+/->-ISOCORYNOLINE, AND <+/->-EPIISOCORYNOLINE FROM CORYSAMINE

10.1016/S0040-4039(00)82413-2

The research focuses on the biomimetic synthesis of hexahydrobenzo[c]phenanthridine alkaloids, specifically (+)-corynoline, (+)-ll-epicorynoline, (+)-isocorynoline, and (+)-ll-epiisocorynoline, from the protoberberine alkaloid corysamine. The purpose of this study was to develop a novel and efficient synthetic route that mimics the biogenetic process, providing a general method for the synthesis of these alkaloids. The researchers achieved this by transforming corysamine into the target alkaloids through a series of chemical reactions involving enamine-aldehyde (3) as a proposed biogenetic intermediate. Key chemicals used in the process included thallium (III) nitrate for oxygenation, sodium borohydride, hydrochloric acid, and sodium cyanoborohydride for reduction and cyclization, as well as lithium aluminum hydride and sodium cyanoborohydride for further reduction steps. The conclusions of the study were that the developed synthetic method was not only biomimetic but also simple and efficient, offering a practical approach to synthesizing hexahydrobenzo[c]phenanthridine alkaloids.

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