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1,1,5-Trimethylfuro[3,4-c]pyridine-3,4(1H,5H)-dione, also known as cerpegin or cerpegine, is a pyridone alkaloid that has been synthesized through various methods, including metalation of pi-deficient heterocycles, one-pot multi-step reactions, and alkylation of intermediates derived from precursors like (-)-carvone or 2-methoxynicotinic acid. Key synthetic strategies involve lithiation, alkylation with methyl iodide, and catalysis by cesium carbonate, yielding the compound efficiently with high overall yields (up to 75%). Its structure features a fused furopyridine core with three methyl groups and two carbonyl groups, highlighting its significance as a synthetic target in alkaloid chemistry.

129748-28-3

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129748-28-3 Usage

Chemical compound

A substance formed by a chemical reaction and consisting of a single type of molecule.

Complex molecular structure

The compound has a complex arrangement of atoms and bonds.

Heterocycle

A type of organic compound that contains a ring of atoms with at least one atom being different from carbon.

Furan ring

A heterocyclic compound consisting of a five-membered ring with four carbon atoms and one oxygen atom.

Pyridine ring

A heterocyclic compound consisting of a six-membered ring with alternating carbon and nitrogen atoms.

Pharmaceutical research

The compound is used in the study and development of drugs and medications.

Medicinal agent

The compound has potential for use in the treatment of various diseases.

Unique structure and properties

The compound has a distinct arrangement of atoms and bonds that give it specific characteristics.

Treatment of diseases

The compound has been studied for its potential use in treating various diseases, although further research is needed.

Organic chemistry

The field of chemistry that deals with the study of carbon-containing compounds and their reactions.

Further research needed

More studies are required to fully understand the compound's potential applications and effects.

Check Digit Verification of cas no

The CAS Registry Mumber 129748-28-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,9,7,4 and 8 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 129748-28:
(8*1)+(7*2)+(6*9)+(5*7)+(4*4)+(3*8)+(2*2)+(1*8)=163
163 % 10 = 3
So 129748-28-3 is a valid CAS Registry Number.

129748-28-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1,5-trimethylfuro[3,4-c]pyridine-3,4-dione

1.2 Other means of identification

Product number -
Other names Cerpegin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:129748-28-3 SDS

129748-28-3Downstream Products

129748-28-3Relevant academic research and scientific papers

Metalation of pi-deficient heterocycles a facile synthesis of cerpegin

Guillier, Fabricee,Nivoliers, Francois,Bourguignon, Jean,Dupas, Georges,Marsais, Francis,Godard, Alain,Queguiner, Guy

, p. 7355 - 7356 (1992)

The first total synthesis of the naturally occuring cerpegin is described. Metalation of a pyridine derivative has been used in the key step.

One-pot three steps synthesis of cerpegin

Villemin, Didier,Liao, Liang

, p. 8733 - 8734 (1996)

Cerpegin 1 was synthesized in a one-pot reaction at room temperature catalysed by cesium carbonate with an overall of 75% yield. 3-Hydroxy-3-methyl-2-butanone 2 reacted with diethyl malonate 3 to give 2-ethoxycarbonyl-3,4,4-trimethyl-2-buten-4-olide 4. Then 4 with s-triazine gave to 1,1-dimethylfuro[3,4-c]pyridine-3,4(1H, 5H)-dione 5 and which was alkylated with methyliodide to cerpegin.

Convenient synthesis of cerpegin

Avetisyan, Aida,Karapetyan, Lousine

, p. 2607 - 2609 (2010)

A convenient procedure for the preparation of cerpegin is described. Taylor & Francis Group, LLC.

'One-pot' four-step synthesis of cerpegin

Lazaar, Jalal,Hoarau, Christophe,Mongin, Florence,Trécourt, Francois,Godard, Alain,Quéguiner, Guy,Marsais, Francis

, p. 3811 - 3813 (2005)

Cerpegin (1) was synthesized through a 'one-pot' reaction in 71% overall yield. Lithiation of commercially available 2-methoxynicotinic acid (2) as its lithium salt using LTMP, followed by addition of acetone at low temperature and a specific acidic treatment of the intermediate 3 thus obtained, gave the 1,1-dimethyl-3,4-dioxo-1,3,4,5-tetrahydrofuro[3,4-c]pyridine (4). The latter was finally selectively alkylated using methyl iodide and caesium carbonate to afford cerpegin (1).

Two versatile routes towards Cerpegin and analogues: Applications of a one pot reaction to new analogues of Cerpegin

Villemin, Didier,Cheikh, Nawel,Liao, Liang,Bar, Nathalie,Lohier, Jean-Fran?ois,Sopkova, Jana,Choukchou-Braham, Noureddine,Mostefa-Kara, Bachir

, p. 4906 - 4918 (2012/07/28)

Simple and efficient routes to the natural alkaloid Cerpegin and new analogues are described herein. In a first approach, we extend the scope of a one pot three steps reaction, which permits the synthesis of new analogues of Cerpegin, substituted in different ways. In a second line of approach, we present an unprecedented synthesis of Cerpegin and analogues where methylfuranones are condensed with dimethylformamide diethylacetal (DMFDEA) to yield enaminolactone esters, which react easily with various primary amines affording Cerpegin and new analogues. We applied this second approach to the synthesis of new bis-Cerpegins and N-amino-Cerpegins. Most of the syntheses are performed under environmental friendly conditions.

Alternative synthesis of a pyridone alkaloid, cerpegin

Matsuo, Keizo

, p. 1191 - 1195 (2007/10/03)

A new pyridone alkaloid, cerpegin was synthesized starting from (-)-carvone.

Synthesis of a pyridone alkaloid, cerpegin

Matsuo,Arase

, p. 2091 - 2094 (2007/10/03)

A new pyridone alkaloid, cerpegin, was synthesized in five steps starting from the Michael reaction between phenylthioacetonitrile and 2- methoxycarbonyl-4-methyl-2-penten-4-olide. Catalytic hydrogenation of a nitrile group in the presence of a conjugated

Synthesis of cerpegin

Matsuo,Arase

, p. 715 - 717 (2007/10/02)

Cerpegin (1), a new pyridone alkaloid, was synthesized starting from the Michael reaction of phenylthioacetonitrile (2) and 2-methoxycarbonyl-4,4- dimethyl-2-buten-4-olide (3) in five steps. Catalytic hydrogenation of a nitrile group in the presence of a

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