10-Hydroxycanthin-6-one

Base Information

• Chemical Name: 10-Hydroxycanthin-6-one
• CAS No.: 86293-41-6
• Molecular Formula: C14H8 N2 O2
• Molecular Weight: 236.23
• NSC Number: 341583
• DSSTox Substance ID: DTXSID40235475
• Nikkaji Number: J427.583G
• Wikidata: Q27134576
• Metabolomics Workbench ID: 64367
• ChEMBL ID: CHEMBL454311
• Mol file: 86293-41-6.mol

Synonyms:10-hydroxycanthin-6-one;86293-41-6;ervine;CHEBI:66064;NSC-341583;10-Hydroxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one;6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one, 10-hydroxy-;12-hydroxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one;6H-Indolo[3,2,1-de][1,5]naphthyridin-6-one, 10-hydroxy-;NSC341583;CHEMBL454311;DTXSID40235475;AKOS040760903;NSC 341583;CANTHIN-6-ONE, HYDROXY-K-215 B815099;Q27134576;12-hydroxy-1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one

Chemical Property of 10-Hydroxycanthin-6-one

Chemical Property:

• Vapor Pressure: 2.6E-07mmHg at 25°C
• Boiling Point: 410.1°Cat760mmHg
• Flash Point: 201.8°C
• PSA: 54.60000
• Density: 1.53g/cm³
• LogP: 2.14430
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 236.058577502
• Heavy Atom Count: 18
• Complexity: 409

Purity/Quality:

≥98% ^*data from raw suppliers

10-Hydroxycanthin-6-one ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)C3=C4N2C(=O)C=CC4=NC=C3
• Description: The empirical formula for this alkaloid should read C21H24N203 and the structure is that given above. This alkaloid has been fully described by Malikov and his colleagues. It forms colourless crystals with m.p. 222-3°C from MeOH and has the following specific rotations: [α]D- 57.3° (c 2.01, MeOH) and [α] D - 83.5° (c 0.3, pyridine). Among the crystalline salts and derivatives that have been prepared are the hydrochloride, m.p. 265-8°C; hydrobromide, m.p. 285-6°C; hydriodide, m.p. 255-8°C and the methiodide, m.p. 258-260°C.

Technology Process of 10-Hydroxycanthin-6-one

There total 5 articles about 10-Hydroxycanthin-6-one 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: 63.0%

10-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one (86293-40-5) → 10-hydroxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one (86293-41-6)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.3390/molecules21030390

Reference yield:

N-benzyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine (25119-60-2) → 10-hydroxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one (86293-41-6)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / toluene; 1,4-dioxane / 48 h / 180 °C / Dean-Stark

2: ammonium formate; 5%-palladium/activated carbon / methanol; toluene / 4 h / 80 °C

3: 5%-palladium/activated carbon / 5,5-dimethyl-1,3-cyclohexadiene / 96 h / Reflux

4: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere

With 5%-palladium/activated carbon; ammonium formate; boron tribromide; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; toluene;

DOI:10.3390/molecules21030390

Reference yield:

3-benzyl-10-methoxy-1,2,3,3a,4,5-hexahydro-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one → 10-hydroxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one (86293-41-6)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium formate; 5%-palladium/activated carbon / methanol; toluene / 4 h / 80 °C

2: 5%-palladium/activated carbon / 5,5-dimethyl-1,3-cyclohexadiene / 96 h / Reflux

3: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere

With 5%-palladium/activated carbon; ammonium formate; boron tribromide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; toluene;

DOI:10.3390/molecules21030390

upstream raw materials:

N-benzyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

2-(5-methoxyindol-3-yl)ethylamine

10-methoxy-1,2,3,3a,4,5-hexahydro-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one

10-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one

Refernces

• 1、 Zhao, Fei,Dai, Jiang-Kun,Liu, Dan,Wang, Shi-Jun,Wang, Jun-Ru. "Synthesis and evaluation of ester derivatives of 10-hydroxycanthin-6-one as potential antimicrobial agents". . . Retrieved 2016/04/20.