Mahanimbine

Base Information

• Chemical Name: Mahanimbine
• CAS No.: 21104-28-9
• Molecular Formula: C₂₃H₂₅NO
• Molecular Weight: 331.458
• Mol file: 21104-28-9.mol

Synonyms:3,5-dimethyl-3-(4-methyl-pent-3-enyl)-3,11-dihydro-pyrano[3,2-a]carbazole;Pyrano(3,2-a)carbazole,3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)-,(+);(+)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)pyrano[3,2-a]carbazole,Mahanimbin;3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3,11-dihydropyrano[3,2-a]carbazole;dl-mahanimbine;(+-)-Mahanimbin;Mahanimbine;dehydroxy-mahanine;Dihydromahanimbin;Rel-(+)-Mahanimbine;(+)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-pentenyl)pyrano[3,2-a]carbazole;

Chemical Property of Mahanimbine

Chemical Property:

• Vapor Pressure: 9.76E-10mmHg at 25°C
• Melting Point: 94-95 °C
• Boiling Point: 502.6°C at 760 mmHg
• PKA: 17.31±0.40(Predicted)
• Flash Point: 178.3°C
• PSA: 25.02000
• Density: 1.109g/cm³
• LogP: 6.54020

Purity/Quality:

99% ^*data from raw suppliers

Mahanimbine analytical standard ^*data from reagent suppliers

Safty Information:

• Statements: 53

MSDS Files:

Useful:

• 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.

Technology Process of Mahanimbine

There total 15 articles about Mahanimbine 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: 91.0%

3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11-tosyl-6-(trimethylsilyl)-3,11-dihydropyrano[3,2-a]carbazole → mahanimbine (21104-28-9,24948-14-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 - 80 ℃; for 6h; Sealed tube;

DOI:10.1021/jacs.6b09628

Reference yield: 82.0%

2-hydroxy-3-methyl-9H-carbazole (24224-30-4) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5,96680-15-8) → mahanimbine (21104-28-9,24948-14-9)

Guidance literature:

With titanium(IV)isopropoxide; In toluene; at -78 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1002/chem.201301792

Reference yield: 49.0%

C23H25NO → mahanimbine (21104-28-9,24948-14-9)

Guidance literature:

In toluene; at 111 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201301792

upstream raw materials:

2-hydroxy-3-methyl-9H-carbazole

(E/Z)-3,7-dimethyl-2,6-octadienal

2-(benzyloxy)-1-methyl-4-nitrobenzene

3-(benzyloxy)-4-methylaniline

Downstream raw materials:

3,5,11-trimethyl-3-(4-methyl-pent-3-enyl)-3,11-dihydro-pyrano[3,2-a]carbazole

mahanimbidine

mahanimbinol

murrayazolinine

Refernces

• 1、 Narasimhan,Paradkar,Gokhale. "Synthesis of girinimbine and (plus or minus) mahanimbine.". . p. 1665 - 1668. Retrieved 1970.
• 2、 Narasimhan et al.. "". . p. 5501. Retrieved 1968.
• 3、 Wang, Tao,Hoye, Thomas R.. "Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family". supporting information. p. 13870 - 13873. Retrieved 2016/11/06.