Koenigine

Base Information

• Chemical Name: Koenigine
• CAS No.: 28513-33-9
• Molecular Formula: C19H19 N O3
• Molecular Weight: 309.365
• DSSTox Substance ID: DTXSID301170207
• Nikkaji Number: J21.645C
• Wikidata: Q104973358
• Metabolomics Workbench ID: 44254
• Mol file: 28513-33-9.mol

Synonyms:Koenigine;28513-33-9;Kenigine;8-methoxy-3,3,5-trimethyl-11H-pyrano[3,2-a]carbazol-9-ol;3,11-Dihydro-8-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazol-9-ol;CHEBI:168437;DTXSID301170207;AKOS040763243;3,11-Dihydro-8-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazol-9-ol, 9CI;13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1,3,7,9,11,13,15-heptaen-14-ol

Chemical Property of Koenigine

Chemical Property:

• Melting Point: 183-5°C
• Boiling Point: 523.9±50.0 °C(Predicted)
• PKA: 10.12±0.40(Predicted)
• PSA: 54.48000
• Density: 1.266±0.06 g/cm3(Predicted)
• LogP: 4.52790
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 309.13649347
• Heavy Atom Count: 23
• Complexity: 491

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C3=C1OC(C=C3)(C)C)NC4=CC(=C(C=C42)OC)O
• Description: The leaves of Murraya koenigii Spreng. yield this carbazole alkaloid. It contains one methoxyl, one hydroxyl and three methyl groups, two of the latter being gem dimethyls.

Technology Process of Koenigine

There total 1 articles about Koenigine 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:

5-bromo-2-methoxyphenol (37942-01-1) → koenigine (28513-33-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1H-imidazole / dichloromethane / 2 h / 20 °C

2: palladium diacetate; caesium carbonate; XPhos / toluene / 19.5 h / Reflux

3: palladium diacetate; copper diacetate; acetic acid / 1 h / 130 °C / Microwave irradiation

4: palladium 10% on activated carbon; hydrogen; ethyl acetate / 19 h / 20 °C / 760.05 Torr

5: titanium(IV) isopropylate / toluene / 15.5 h / 20 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; copper diacetate; palladium diacetate; caesium carbonate; acetic acid; ethyl acetate; XPhos; In tetrahydrofuran; dichloromethane; toluene; 2: |Buchwald-Hartwig Coupling;

DOI:10.1055/s-0035-1560359

Reference yield: 20.0%

koenigine (28513-33-9) + 4-hydroxy-3,5-dimethoxycinnamic acid methyl ester (42041-51-0,67460-46-2,20733-94-2) → C31H31NO8

Guidance literature:

With dichlorobis(tricyclohexylphosphine)palladium(II); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20 ℃; for 5h; Inert atmosphere;

upstream raw materials:

5-bromo-2-methoxyphenol

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