Isomahanimbine

Base Information

• Chemical Name: Isomahanimbine
• CAS No.: 26871-46-5
• Molecular Formula: C₂₃H₂₅NO
• Molecular Weight: 331.458
• Mol file: 26871-46-5.mol

Synonyms:Isomahanimbine(8CI); Pyrano[3,2-a]carbazole, 3,11-dihydro-3,8-dimethyl-3-(4-methyl-3-pentenyl)-;Pyrano[3,2-a]carbazole, 3,11-dihydro-3,8-dimethyl-3-(4-methyl-3-pentenyl)-,(-)- (9CI); Isomahanimbin

Chemical Property of Isomahanimbine

Chemical Property:

• Melting Point: 142°C
• PSA: 25.02000
• LogP: 6.54020

Purity/Quality:

98.5% ^*data from raw suppliers

Isomahanimbine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: The roots and leaves of Murraya koenigii Spreng. yield this alkaloid which is best crystallized from CH2 C1r hexane. It has [α]D - 6° (c 2.01, CHC1 3 ) and the ultraviolet spectrum in EtOH shows absorption maxima at 225, 278, 281, 295, 335 and 354 mp. Catalytic hydrogenation with Pd-C gives the tetrahydro deriva_x0002_tive, m.p. l66-7°C, as colourless crystals from pentane, the ultraviolet spectrum of which has absorption maxima at 220, 241, 255,260,306 and 320 mp. Treatment with methyl sulphate in NaOH yields the N-methyl compound, m.p. 94°C, giving an ultraviolet spectrum in EtOH consisting of absorption maxima at 240, 293,332,345 and 358 mp.

Technology Process of Isomahanimbine

There total 18 articles about Isomahanimbine 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: 79.0%

C20H17NO3S (1616967-63-5) + 3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate (104846-78-8) → mahanimbicine (26871-46-5,28305-77-3,28305-78-4) + C23H25NO (1616967-62-4)

Guidance literature:

C₂₀H₁₇NO₃S; 3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate; With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 22h; Inert atmosphere;

In 5,5-dimethyl-1,3-cyclohexadiene; for 27.5h; Inert atmosphere; Reflux;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 70 - 75 ℃; for 6h; Inert atmosphere; Microwave irradiation;

DOI:10.1039/c4ob01151a

Reference yield: 49.0%

2-hydroxy-6-methylcarbazole (26870-61-1) + 3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate (104846-78-8) → mahanimbicine (26871-46-5,28305-77-3,28305-78-4) + 1,7-dimethyl-2-methylene-1-(4-methylpent-3-en-1-yl)-1,10-dihydro-2H-furo[3,2-a]carbazole

Guidance literature:

2-hydroxy-6-methylcarbazole; 3,7-dimethyl-oct-6-en-1-yn-3-yl methyl carbonate; With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 22h; Inert atmosphere;

In toluene; for 22.5h; Reflux; Inert atmosphere;

DOI:10.1039/c4ob01151a

Reference yield:

3-methoxyphenyl bromide (2398-37-0) → mahanimbicine (26871-46-5,28305-77-3,28305-78-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium diacetate; caesium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 17.5 h / Reflux; Inert atmosphere

2.1: palladium diacetate; potassium carbonate; Trimethylacetic acid / 20.5 h / 100 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 2 h / -78 - 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) iodide / acetonitrile / 22 h / 20 °C / Inert atmosphere

4.2: 22.5 h / Reflux; Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; copper(l) iodide; palladium diacetate; boron tribromide; potassium carbonate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; Trimethylacetic acid; In dichloromethane; toluene; acetonitrile;

DOI:10.1039/c4ob01151a

upstream raw materials:

2-hydroxy-6-methylcarbazole

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

3-methoxyphenyl bromide

N-(3-methoxyphenyl)-4-methylaniline

Refernces