(+)-Corlumine

Base Information

• Chemical Name: (+)-Corlumine
• CAS No.: 485-51-8
• Molecular Formula: C21H21NO6
• Molecular Weight: 383.43
• Nikkaji Number: J67.650K
• Wikidata: Q76303469
• Mol file: 485-51-8.mol

Synonyms:Corlumine;(+)-Corlumine;(+)-Carlumine;NSC 32983;Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)-, (R-(R*,S*))-;SCHEMBL679701

Chemical Property of (+)-Corlumine

Chemical Property:

• Vapor Pressure: 8.17E-12mmHg at 25°C
• Boiling Point: 542.1°Cat760mmHg
• Flash Point: 281.6°C
• PSA: 66.46000
• Density: 1.339g/cm³
• LogP: 2.81110
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 383.13688739
• Heavy Atom Count: 28
• Complexity: 601

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1C3C4=C(C5=C(C=C4)OCO5)C(=O)O3)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@H]1[C@H]3C4=C(C5=C(C=C4)OCO5)C(=O)O3)OC)OC
• Uses: Agricultural chemical.

Technology Process of (+)-Corlumine

There total 40 articles about (+)-Corlumine 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: 80.0%

carbon monoxide (201230-82-2) + erythro-1-(2-bromo-3,4-(methylenedioxy)-α-hydroxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline → (+/-)-corlumine (485-51-8,524-46-9,21414-43-7,30770-75-3,38184-69-9,64397-12-2,79082-64-7)

Guidance literature:

With chloro-trimethyl-silane; Pd(PPh₃)(OAc)2; potassium carbonate; In toluene; at 140 ℃; for 24h;

DOI:10.1021/jo982451w

Reference yield: 60.0%

carbon monoxide (201230-82-2) + 1-(2-bromo-3,4-(methylenedioxy)-α-hydroxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline → (+/-)-adlumine (485-51-8,524-46-9,21414-43-7,30770-75-3,38184-69-9,64397-12-2,79082-64-7) + (+/-)-corlumine (485-51-8,524-46-9,21414-43-7,30770-75-3,38184-69-9,64397-12-2,79082-64-7)

Guidance literature:

With chloro-trimethyl-silane; Pd(PPh₃)(OAc)2; potassium carbonate; In toluene; at 140 ℃; for 24h;

DOI:10.1021/jo982451w

Reference yield: 60.0%

carbon monoxide (201230-82-2) + 1-(2-bromo-3,4-(methylenedioxy)-α-hydroxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline → (+/-)-adlumine (485-51-8,524-46-9,21414-43-7,30770-75-3,38184-69-9,64397-12-2,79082-64-7) + (+/-)-corlumine (485-51-8,524-46-9,21414-43-7,30770-75-3,38184-69-9,64397-12-2,79082-64-7)

Guidance literature:

With chloro-trimethyl-silane; Pd(PPh₃)(OAc)2; potassium carbonate; In toluene; at 140 ℃; for 24h;

DOI:10.1021/jo982451w

upstream raw materials:

(+/-)-corlumine

formaldehyd

carbon dioxide

(R)-Benzo[1,3]dioxol-5-yl-((S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-methanol

Downstream raw materials:

(+)-corlumine

Refernces

THE BIOSYNTHESIS OF THE ALKALOIDS OF CORYDALIS MEIFOLIA WALL.

10.1016/S0040-4020(01)87469-X

The study investigates the biosynthesis of alkaloids in Corydalis meifolia Wall., a plant used in traditional medicine. The researchers used tracer experiments to demonstrate that the alkaloids corlumine, cavidine, and yenshusomine are stereospecifically biosynthesized from (R)-(?)-reticuline. They fed various labeled precursors, including tyrosine, norreticuline, and reticuline, to young branches of the plant and observed the incorporation of these precursors into the target alkaloids. The results showed that certain precursors, like norreticuline and reticuline, were efficiently metabolized into the alkaloids, while others were not. The study also established the regiospecificity of the biosynthetic pathway by tracking the labeled atoms through various chemical transformations, confirming that reticuline is a true precursor of these alkaloids. The findings provide valuable insights into the biogenetic pathway of these medically relevant compounds.

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