Mukonine

Base Information

• Chemical Name: Mukonine
• CAS No.: 23523-94-6
• Molecular Formula: C15H13 N O3
• Molecular Weight: 255.273
• DSSTox Substance ID: DTXSID201263982
• Nikkaji Number: J20.717I
• Wikidata: Q105009067
• Metabolomics Workbench ID: 44325
• ChEMBL ID: CHEMBL236143
• Mol file: 23523-94-6.mol

Synonyms:mukonine

Chemical Property of Mukonine

Chemical Property:

• Melting Point: 195-197 °C
• Boiling Point: 459.9±25.0 °C(Predicted)
• PKA: 16.47±0.30(Predicted)
• PSA: 51.32000
• Density: 1.290±0.06 g/cm3(Predicted)
• LogP: 3.11630
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 255.08954328
• Heavy Atom Count: 19
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1NC3=CC=CC=C32)C(=O)OC

Technology Process of Mukonine

There total 44 articles about Mukonine 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: 99.0%

9-acetyl-1-methoxy-3-methoxycarbonyl-9H-carbazole (1058140-90-1) → 1-methoxy-3-methoxycarbonyl-9H-carbazole (23523-94-6)

Guidance literature:

With sulfuric acid; In methanol; at 80 ℃; for 0.166667h;

DOI:10.1021/jo801273q

Reference yield: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + methyl 1-hydroxy-9H-carbazole-3-carboxylate (182261-83-2) → 1-methoxy-3-methoxycarbonyl-9H-carbazole (23523-94-6)

Guidance literature:

In methanol; diethyl ether; at 0 ℃; for 12h;

DOI:10.1016/j.tetlet.2016.01.002

Reference yield: 97.0%

N-(tert-butoxycarbonyl)-1-methoxy-3-(methoxycarbonyl)carbazole (834899-25-1) → 1-methoxy-3-methoxycarbonyl-9H-carbazole (23523-94-6)

Guidance literature:

With trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; at 0 - 20 ℃; for 2.25h;

DOI:10.1021/jo048472+

upstream raw materials:

diazomethane

methyl 1-hydroxy-9H-carbazole-3-carboxylate

dimethyl sulfate

methyl 3-methoxy-4-aminobenzoate

Downstream raw materials:

mukoeic acid

C₂₁H₁₉NO₄S

3-chloromethyl-1-methoxy-9-tosyl-9H-carbazole

C₂₂H₁₉NO₅S

Refernces

Lateral lithiation-initiated annulations in the synthesis of 1-oxygenated carbazole alkaloids and a cycloheptacarbazole

10.1055/s-0031-1290380

The research focuses on the development of an efficient synthetic route to 1-oxygenated carbazole alkaloids, which are key structural motifs in various biologically active alkaloids and pharmaceuticals. The study introduces an anionic [4+2] annulation of lithiated furoindolones with dimethyl maleate, followed by selective demethoxycarbonylation, to synthesize 3-methoxycarbonylcarbazoles. This method led to the straightforward synthesis of two natural products, clausine E and mukonine, as well as their 4-prenyl analogues. Additionally, the research uncovered a new route to cyclohepta[d,e,f]carbazole. The conclusions of the study highlight the potential of this annulation strategy for the synthesis of carbazole natural products and the discovery of an unprecedented cyclization leading to the formation of a cycloheptacarbazole motif.