ISOMAHANINE

Base Information

• Chemical Name: ISOMAHANINE
• CAS No.: 144606-95-1
• Molecular Formula: C₂₃H₂₅NO₂
• Molecular Weight: 347.457
• Mol file: 144606-95-1.mol

Synonyms:Isomahanine

Chemical Property of ISOMAHANINE

Chemical Property:

• PSA: 45.25000
• LogP: 6.24580

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Isomahanine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ISOMAHANINE

There total 10 articles about ISOMAHANINE 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: 100.0%

O-(triisopropylsilyl)pyrayafoline D (1643448-03-6) → pyrayafoline D (38826-50-5,138876-26-3,144606-95-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; at -5 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1039/c4ob00367e

Reference yield:

N-(3-methoxyphenyl)-4-methyl-3-(triisopropylsilyloxy)aniline (1643447-98-6) → pyrayafoline D (38826-50-5,138876-26-3,144606-95-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper diacetate; Trimethylacetic acid; palladium diacetate / 3 h / 110 °C / Microwave irradiation; Inert atmosphere

2.1: boron tribromide / dichloromethane / 14.8 h / -78 - 20 °C / Inert atmosphere

3.1: copper dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 30.5 h / 20 °C / Inert atmosphere

3.2: 23 h / Reflux; Inert atmosphere

4.1: tetrabutyl ammonium fluoride / N,N-dimethyl-formamide; tetrahydrofuran / 0.17 h / -5 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; copper diacetate; palladium diacetate; boron tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride; Trimethylacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c4ob00367e

Reference yield:

5-bromo-2-methylphenol (36138-76-8) → pyrayafoline D (38826-50-5,138876-26-3,144606-95-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 21.5 h / 20 °C / Inert atmosphere

2.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; caesium carbonate; palladium diacetate / toluene / 28 h / 100 °C / Inert atmosphere

3.1: copper diacetate; Trimethylacetic acid; palladium diacetate / 3 h / 110 °C / Microwave irradiation; Inert atmosphere

4.1: boron tribromide / dichloromethane / 14.8 h / -78 - 20 °C / Inert atmosphere

5.1: copper dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 30.5 h / 20 °C / Inert atmosphere

5.2: 23 h / Reflux; Inert atmosphere

6.1: tetrabutyl ammonium fluoride / N,N-dimethyl-formamide; tetrahydrofuran / 0.17 h / -5 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 1H-imidazole; tetrabutyl ammonium fluoride; copper diacetate; palladium diacetate; boron tribromide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride; Trimethylacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: |Buchwald-Hartwig Coupling;

DOI:10.1039/c4ob00367e

upstream raw materials:

N-(3-methoxyphenyl)-4-methyl-3-(triisopropylsilyloxy)aniline

5-bromo-2-methylphenol

4-bromo-2-(triisopropylsilyloxy)toluene

7-methoxy-3-methyl-2-(triisopropylsilyloxy)-9H-carbazole

Refernces