53948-09-7

Basic information

• Product Name: aristololactam BII
• Synonyms: aristololactam BII;1,2-Dimethoxy-4,5-dihydrodibenzo[cd,f]indole-4-one;1,2-Dimethoxydibenz[cd,f]indol-4(5H)-one;Aristolactam BII;Cepharanone B;Aristolochic acid BII
• CAS NO: 53948-09-7
• Molecular Formula: C17H13NO3
• Molecular Weight: 279.29002
• Mol File: 53948-09-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 264-265 °C
• Boiling Point: 429.7 °C at 760 mmHg
• Flash Point: 213.7 °C
• Appearance: /
• Density: 1.332 g/cm³
• Vapor Pressure: 1.37E-07mmHg at 25°C
• Refractive Index: 1.708
• PKA: 12.31±0.20(Predicted)
• CAS DataBase Reference: aristololactam BII(CAS DataBase Reference)
• NIST Chemistry Reference: aristololactam BII(53948-09-7)
• EPA Substance Registry System: aristololactam BII(53948-09-7)

Safety Data

• Hazardous Substances Data: 53948-09-7(Hazardous Substances Data)

Usage

Description

This base, isolated from the callus tissue of Stephania cepharantha, is the domethoxy analogue of cepharanone A and forms a mass of pale yellow needles when crystallized from EtOH. Like the preceding alkaloid, it gives a blue fluorescence and the ultraviolet spectrum in EtOH is highly complex with absorption maxima at 232, 263, 276, 287,319 and 396 nm.

References

Akasu, Itokawa, Fujita, Tetrahedron Lett., 3609 (1974)

InChI:InChI=1/C17H13NO3/c1-20-13-8-11-14-12(18-17(11)19)7-9-5-3-4-6-10(9)15(14)16(13)21-2/h3-8H,1-2H3,(H,18,19)

Upstream product

• 144709-20-6 3,4-dimethoxy-6-iodobenzamide 
• 61203-48-3 2-iodo-4,5-dimethoxybenzoic acid 
• 1310569-45-9 4,5-dimethoxy-2-(2-oxo-2-phenyl-acetyl)-benzaldehyde 
• 1042722-42-8 4-bromo-5,6-dimethoxyisoindolin-1-one 
• 40138-16-7 2-formylbenzene boronic acid 
• 144266-50-2 methyl 2-(2'-bromophenylacetyl)-4,5-dimethoxyphenylacetate 
• 144266-53-5 1,2-dimethoxy-6a,7-dehydrodibenzochromanone 
• 144266-54-6 3,4-dimethoxy-9,10-dehydrodibenzocoumaranone 
• 186581-53-3 diazomethane 
• 112501-42-5 piperolactam A 
• 53948-07-5 aristololactam A II 

Downstream Products

• 112501-42-5 piperolactam A 

Relevant articles and documents

ARISTOLACTAMS AND 4,5-DIOXOAPORPHINES FROM PIPER LONGUM

Nine alkaloids were isolated from the cold ethanol extract of Piper longum roots, of which six known compounds were identified as cepharadione B, cepharadione A, cepharanone B, aristolactam AII, norcepharadione B, and 2-hydroxy-1-methoxy-4H-dibenzoquinoline-4,5(6H)-dione.The three new alkaloids were characterized as 10-amino-4-hydroxy-3-methoxyphenanthrene-1-carboxylic acid lactam , 10-amino-4-hydroxy-2,3-dimethoxyphenanthrene-1-carboxylic acid lactam and 2-hydroxy-1-methoxy-6-methyl-4H-dibenzoquinoline-4,5(6H)-dione .Key Word Index - Piper longum; Piperaceae; root alkaloids; aristolactams; dioxoaporphines; piperolactam A; piperolactam B; piperadione; NMR.

A simple, efficient route to the synthesis of dibenzocoumaranones and aristolactams

We report the first synthesis of dibenzo[cdf]coumaranones that could be readily transformed into their nitrogen analogues, the aristolactams.

Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (E)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant

Regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones via Pd(II)/Cu(II)-catalyzed one-pot C-C/C-N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency. Further elaboration of the products obtained from this process enabled very short and efficient syntheses of aristolactam and indoloisoquinolinone alkaloids.

Total synthesis of aristolactam alkaloids: Via synergistic C-H bond activation and dehydro-Diels-Alder reactions

A concise total synthesis of aristolactam alkaloids by a synergistic combination of C-H bond activation and dehydro-Diels-Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones via a ruthenium-catalyzed C-H bond activation, and a dehydro-Diels-Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benzynes, were developed. The method presented allows the opportunity for the construction of all the rings of aristolactams from easily available starting materials.