21104-28-9

Basic information

• Product Name: Mahanimbine
• Synonyms: Mahanimbine;(+)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)pyrano[3,2-a]carbazole;Mahanimbin
• CAS NO: 21104-28-9
• Molecular Formula: C₂₃H₂₅NO
• Molecular Weight: 331.4507
• Mol File: 21104-28-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 94-95 °C
• Boiling Point: 502.6°C at 760 mmHg
• Flash Point: 178.3°C
• Appearance: /
• Density: 1.109
• Vapor Pressure: 9.76E-10mmHg at 25°C
• Refractive Index: 1.634
• PKA: 17.31±0.40(Predicted)
• CAS DataBase Reference: Mahanimbine(CAS DataBase Reference)
• NIST Chemistry Reference: Mahanimbine(21104-28-9)
• EPA Substance Registry System: Mahanimbine(21104-28-9)

Safety Data

• Statements: 53
• WGK Germany: 3
• Hazardous Substances Data: 21104-28-9(Hazardous Substances Data)

Usage

Description

The leaves of Murraya koenigii Spreng. also furnish this crystalline alkaloid which is dextrorotatory with [α]D + 52° (CHCI3). The ultraviolet spectrum exhibits several absorption maxima occurring at 227, 288,300,315,328,343 and 357 mil. It furnishes a crystalline picrate as pale yellow needles, m.p. 142°C and on catalytic reduction gives the dihydro derivative, m.p. 101°C and finally the tetrahydro compound, m.p. 108°C. Spectroscopic and chemical data support the structure given above.

References

Chakraborty, Das, Bose., Sci. Cult. (Calcutta), 32, 83 (1966) Structure: Narasimhan, Paradkar, Chitguppi., Tetrahedron Lett., 5501 (1968)

InChI:InChI=1/C23H25NO/c1-15(2)8-7-12-23(4)13-11-18-21-19(14-16(3)22(18)25-23)17-9-5-6-10-20(17)24-21/h5-6,8-11,13-14,24H,7,12H2,1-4H3

Upstream product

• 24224-30-4 2-hydroxy-3-methyl-9H-carbazole 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 24224-28-0 2-methoxy-3-methyl-9H-carbazole 
• 1072127-10-6 3-methoxy-4-methyl-N-phenylaniline 
• 104846-78-8 3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate 
• 16452-01-0 ortho-cresidine 
• 13120-77-9 2-methyl-5-nitroanisole 
• 5428-54-6 2-methyl-5-nitrophenol 
• 219492-12-3 3-(benzyloxy)-4-methylaniline 
• 219492-11-2 2-(benzyloxy)-1-methyl-4-nitrobenzene 

Downstream Products

• 25488-37-3 mahanimbidine 
• 49620-01-1 murrayazolinine 
• 31077-94-8 bicyclomahanimbine 
• 25488-33-9 murrayazolidine 
• 77156-13-9 mahanimbinol 
• 26871-48-7 3,5,11-trimethyl-3-(4-methyl-pent-3-enyl)-3,11-dihydro-pyrano[3,2-a]carbazole 
• 25488-33-9 Methyl-isopropenylcarbazol 

Relevant articles and documents

Biomimetic Total Synthesis of Rhodonoids C and D, and Murrayakonine D

A divergent, three-step total synthesis of rhodonoids C and D has been achieved using a biosynthetically inspired, acid-catalyzed cascade cyclization of an epoxy-chromene that involves the presumed intermediacy of o-quinone methides. Application of a similar strategy also allowed synthesis of the alkaloid murrayakonine D.

Synthesis of Carbazoles and Carbazole-Containing Heterocycles via Rhodium-Catalyzed Tandem Carbonylative Benzannulations

Polycyclic aromatic compounds are important constituents of pharmaceuticals and other materials. We have developed a series of Rh-catalyzed tandem carbonylative benzannulations for the synthesis of tri-, tetra-, and pentacyclic heterocycles from different types of aryl propargylic alcohols. These tandem reactions provide efficient access to highly substituted carbazoles, furocarbazoles, pyrrolocarbazoles, thiophenocarbazoles, and indolocarbazoles. While tricyclic heterocycles could be derived from vinyl aryl propargylic alcohols, tetra- and pentacyclic heterocycles were synthesized from diaryl propargylic alcohols. The tandem carbonylative benzannulation is initiated by a π-acidic rhodium(I) catalyst-mediated nucleophilic addition to alkyne to generate a key metal-carbene intermediate, which is then trapped by carbon monoxide to form a ketene species for 6π electrocyclization. Overall, three bonds and two rings are formed in all of these tandem carbonylative benzannulation reactions.

Efficient construction of pyrano [3, 2-a]carbazoles: Application to a biomimetic total synthesis of cyclized monoterpenoid pyrano [3, 2-a]carbazole Alkaloids

We have developed a highly efficient route to 2-hydroxy-3-methyl-carbazole (1) via a palladium-catalyzed construction of the carbazole skeleton. Using 1 as relay compound, different methods for annulations of pyran rings by reaction with terpenoid building blocks have been tested. The Lewis acid promoted reaction of 1 with prenal (21) opened up an efficient route to girinimbine (3) and the corresponding reaction with citral (25) afforded mahanimbine (5). Oxidation of compounds 3 and 5 provided murraya-cine (4) and murrayacinine (6). Following the biogenetic proposal, mahanim-bine (5) has been exploited for efficient biomimetic syntheses of the cyclized monoterpenoid pyrano[3, 2-a]carbazole alkaloids cyclomahanimbine (7), maha-nimbidine (8) and bicyclomahanimbine (9). The interconversions of 5, 7, 8 and 9 are described and mechanistic implications are discussed. Structural assignments are unambiguously verified by X-ray crystal structure determinations. Moreover, cyclomahanimbine (7) was transformed into murrayazolinine (10) and exozoline (11).