Koenigicine

Base Information

• Chemical Name: Koenigicine
• CAS No.: 24123-92-0
• Molecular Formula: C20H21 N O3
• Molecular Weight: 323.392
• Hs Code.: 2934999090
• European Community (EC) Number: 803-440-9
• NSC Number: 127151
• DSSTox Substance ID: DTXSID00298965
• Nikkaji Number: J16.484D
• Wikidata: Q72486905
• Metabolomics Workbench ID: 44255
• ChEMBL ID: CHEMBL3893262
• Mol file: 24123-92-0.mol

Synonyms:koenidine

Chemical Property of Koenigicine

Chemical Property:

• Vapor Pressure: 1.21E-09mmHg at 25°C
• Melting Point: 224-225 °C
• Boiling Point: 500.1°C at 760 mmHg
• PKA: 16.88±0.40(Predicted)
• Flash Point: 177.5°C
• PSA: 43.48000
• Density: 1.198
• LogP: 4.83090
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 323.15214353
• Heavy Atom Count: 24
• Complexity: 505

Purity/Quality:

99% ^*data from raw suppliers

Koenigicine phyproof? Reference Substance ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 1224366
• Hazard Codes: Xi
• Statements: 36-53
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C3=C1OC(C=C3)(C)C)NC4=CC(=C(C=C42)OC)OC
• Description: A minor alkaloid, koenigicine occurs in the leaves of Murraya koenigii Spreng. It yields colourless crystals from EtOH and gives an ultraviolet spectrum in EtOH having two absorption maxima at 239 and 361 nm. Catalytic hydrogenation yields the dihydro derivative with m.p. 232°C.

Technology Process of Koenigicine

There total 1 articles about Koenigicine 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) → 8,9-dimethoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole (24123-92-0)

Guidance literature:

Multi-step reaction with 7 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

7: potassium carbonate / acetone / 18.5 h / 56 °C

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

DOI:10.1055/s-0035-1560359

Reference yield: 88.0%

8,9-dimethoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole (24123-92-0) → 11-(2-bromobenzyl)-8,9-dimethoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2019.02.003

Reference yield: 86.0%

8,9-dimethoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole (24123-92-0) → 11-benzyl-8,9-dimethoxy-3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2019.02.003

upstream raw materials:

5-bromo-2-methoxyphenol