CERPEGIN

Base Information

• Chemical Name: CERPEGIN
• CAS No.: 145887-88-3
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.175
• Mol file: 145887-88-3.mol

Synonyms:1,1-dimethylfuro<3,4-c>pyridine-3,4(1H,5H)-dione;;

Chemical Property of CERPEGIN

Chemical Property:

• Appearance/Colour: Beige Solid
• Vapor Pressure: 1.59E-11mmHg at 25°C
• Melting Point: 257-260 oC (ligroine )*
• Refractive Index: 1.574
• Boiling Point: 535.1°C at 760 mmHg
• PKA: 10.51±0.40(Predicted)
• Flash Point: 277.4°C
• PSA: 59.16000
• Density: 1.32±0.1 g/cm3 (20 oC 760 Torr), Calc.
• LogP: 0.78040

Purity/Quality:

98%Min ^*data from raw suppliers

Cerpegin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Cerpegin is a naturally occurring pyridinone alkaloid isolated from Roxb, a tradional indian medicine used as a tranquilizer, anti-inflammatory, analgesic and antiulcer.

Technology Process of CERPEGIN

There total 13 articles about CERPEGIN 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: 94.2%

4-(2-(dimethylamino)vinyl)-5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carbonitrile (1269593-14-7) → 1,1-dimethyl-1H,5H-furo[3,4-c]pyridine-3,4-dione (145887-88-3)

Guidance literature:

With hydrogenchloride; acetic acid; for 4h; Reflux;

DOI:10.1016/j.bmcl.2014.01.072

Reference yield: 94.0%

4-(2-(dimethylamino)vinyl)-5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carbonitrile (1269593-14-7) → 1,1-dimethylfuro<3,4-c>pyridine-3,4(1H,5H)-dione (145887-88-3)

Guidance literature:

With hydrogenchloride; acetic acid; for 4h; Reflux;

DOI:10.1016/j.bmcl.2012.03.105

Reference yield: 90.0%

1,3,5-Triazine (290-87-9) + 3-Hydroxy-3-methyl-2-butanone (115-22-0) + diethyl malonate (105-53-3) → 1,1-dimethylfuro<3,4-c>pyridine-3,4(1H,5H)-dione (145887-88-3)

Guidance literature:

3-Hydroxy-3-methyl-2-butanone; diethyl malonate; With sodium ethanolate; In ethanol; at 20 ℃; for 0.5h;

1,3,5-Triazine; In ethanol; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2012.03.057

upstream raw materials:

1,1-dimethyl-4-methoxyfuro<3,4-c>pyridin-3(1H)-one

1,3,5-Triazine

4,5,5-trimethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

2-methoxynicotinic acid

Downstream raw materials:

4-(benzylamino)-1,1-dimethylfuro[3,4-c]pyridin-3(1H)-one

4-(4-chlorophenylamino)-1,1-dimethyl-1H-furo[3,4-c]pyridin-3-one

4-(1,1-dimethyl-3-oxo-1,3-dihydrofuro[3,4-c]pyridin-4-ylamino)benzenesulfonamide

4-chloro-1,1-dimethylfuro[3,4-c]pyridine-3(1H)-one

Refernces

• 1、 Alves de Sousa, Rodolphe,Arnould, Stéphanie,Bekaddour, Nassima,Dairou, Julien,Diaz, Olivier,Ermellino, Laura,Hayek, Simon,Herbeuval, Jean-Philippe,Hovhannisyan, Anna A.,Lotteau, Vincent,Melikyan, Gagik,Nisole, Sébastien,Pietrancosta, Nicolas,Sardet, Claude,Tramontano, Enzo,Vidalain, Pierre-Olivier. "Cerpegin-derived furo[3,4-c]pyridine-3,4(1H,5H)-diones enhance cellular response to interferons by de novo pyrimidine biosynthesis inhibition". . . Retrieved 2019.
• 2、 Villemin, Didier,Cheikh, Nawel,Liao, Liang,Bar, Nathalie,Lohier, Jean-Fran?ois,Sopkova, Jana,Choukchou-Braham, Noureddine,Mostefa-Kara, Bachir. "Two versatile routes towards Cerpegin and analogues: Applications of a one pot reaction to new analogues of Cerpegin". experimental part. p. 4906 - 4918. Retrieved 2012/07/28.