8-Oxocoptisine

Base Information

• Chemical Name: 8-Oxocoptisine
• CAS No.: 19716-61-1
• Molecular Formula: C19H13NO5
• Molecular Weight: 335.316
• ChEMBL ID: CHEMBL3612189
• DSSTox Substance ID: DTXSID901317158
• Metabolomics Workbench ID: 132806
• Nikkaji Number: J690.353C
• Wikidata: Q104397048
• Mol file: 19716-61-1.mol

Synonyms:8-oxocoptisine

Chemical Property of 8-Oxocoptisine

Chemical Property:

• Melting Point: 283-285℃
• Boiling Point: 617.5±55.0 °C(Predicted)
• PKA: -1.62±0.20(Predicted)
• PSA: 58.92000
• Density: 1.61±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 2.68200
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 335.07937252
• Heavy Atom Count: 25
• Complexity: 621

Purity/Quality:

≥98% ^*data from raw suppliers

8-Oxycoptisine ≥98% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2C(=CC3=C(C2=O)C4=C(C=C3)OCO4)C5=CC6=C(C=C51)OCO6

Technology Process of 8-Oxocoptisine

There total 30 articles about 8-Oxocoptisine 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: 73.0%

coptisine chloride (6020-18-4) → coptisinone (19716-61-1)

Guidance literature:

With sodium hydroxide; potassium hexacyanoferrate(III); In water; for 10h; Reflux;

DOI:10.1080/10286020.2014.932778

Reference yield: 56.0%

13-carboxaldehyde-8-oxocoptisine → coptisinone (19716-61-1)

Guidance literature:

With Wilkinson's catalyst; diphenyl phosphoryl azide; In diethylene glycol dimethyl ether; at 160 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201601245

Reference yield: 53.0%

7-(6-(2-hydroxyethyl)benzo[d][1,3]dioxol-5-yl)-[1,3]dioxolo[4,5-h]isoquinolin-9(8H)-one (688006-48-6) → coptisinone (19716-61-1)

Guidance literature:

With potassium carbonate; p-toluenesulfonyl chloride; In N,N-dimethyl-formamide; at 100 ℃; for 4h;

DOI:10.1021/jo035836+

upstream raw materials:

5,6,8,13-tetrahydro-2,3,9,10-di(methylenedioxy)-8-oxo-13aH-dibenzo[a,g]quinolizine-13a-carboxylic acid

7-(6-(2-hydroxyethyl)benzo[d][1,3]dioxol-5-yl)-[1,3]dioxolo[4,5-h]isoquinolin-9(8H)-one

5-methylbenzo[1,3]dioxole-4-carboxylic acid diethylamide

2-carboxy-3,4-(methylenedioxy)toluene

Downstream raw materials:

coptisine

Stylopine

Refernces

• 1、 Cui, Xiang Juan,Lu, Ying Ying,Zhao, Min,Qian, Shan,Wu, Yong. "The new shortcut synthesis of 8-oxocoptisine". . p. 1281 - 1282. Retrieved 2010.
• 2、 Dostál, Ji?í,Man, Stanislav,Se?ká?ová, Pavlína,Hulová, Dagmar,Ne?as, Marek,Potá?ek, Milan,Tou?ek, Jaromír,Dommisse, Roger,Van Dongen, Walter,Marek, Radek. "Berberine and coptisine free bases". . p. 135 - 142. Retrieved 2004.
• 3、 Ai, Gaoxiang,Huang, Ziwei,Cheng, Juanjuan,Xie, Jianhui,Zeng, Huifang,Liu, Yuhong,Li, Yucui,Huang, Xiaoqi,Chen, Jiannan,Su, Ziren. "Gut Microbiota-Mediated Transformation of Coptisine Into a Novel Metabolite 8-Oxocoptisine: Insight Into Its Superior Anti-Colitis Effect". . . Retrieved 2021/04/19.