Murrayanine

Base Information

• Chemical Name: Murrayanine
• CAS No.: 723-97-7
• Molecular Formula: C14H11NO2
• Molecular Weight: 225.247
• NSC Number: 94931
• UNII: 3NIN8IA768
• DSSTox Substance ID: DTXSID80222627
• Nikkaji Number: J14.178J
• Wikidata: Q27104978
• Metabolomics Workbench ID: 48349
• ChEMBL ID: CHEMBL1689802
• Mol file: 723-97-7.mol

Synonyms:murrayanine

Chemical Property of Murrayanine

Chemical Property:

• Vapor Pressure: 7.08E-09mmHg at 25°C
• Melting Point: 168°C
• Boiling Point: 466.4°C at 760 mmHg
• Flash Point: 235.9°C
• PSA: 42.09000
• Density: 1.312g/cm³
• LogP: 3.14220
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 225.078978594
• Heavy Atom Count: 17
• Complexity: 294

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC2=C1NC3=CC=CC=C32)C=O
• Description: This simple carbazole alkaloid is found in the stem bark of Mu"aya koenigii Spreng. It is best purified by sublimation of the crude base when it yields colour_x0002_less crystals. The ultraviolet spectrum in ethanol has absorption maxima at 238, 247,274,289 and 335 mJJ.. The structure has been shown to be 3-formyl-lmethoxycarbazole by spectroscopic methods and synthesis. It yields an oxime, m.p. l55-6°C; a picrate, m.p. 198-2000 C and the 2:4-dinitrophenylhydrazone, m.p. > 300°C. The N-methyl derivative forms colourless needles from C6H6- light petroleum, m.p. l48-9°C. When subjected to Wolff-Kishner reduction, the alkaline phase yields l-hydroxy-3-methyl-carbazole.

Technology Process of Murrayanine

There total 33 articles about Murrayanine 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: 98.0%

koenoline (3909-78-2) → murrayanine (723-97-7)

Guidance literature:

With manganese(IV) oxide; In acetone; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2016.01.002

Reference yield: 95.0%

1-methoxy-3-methylcarbazole (4532-33-6) → murrayanine (723-97-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5h;

DOI:10.1021/acs.joc.7b03020

Reference yield: 88.0%

1-bromo-9H-carbazole-3-carbaldehyde (1384959-52-7) + sodium methylate (124-41-4) → murrayanine (723-97-7)

Guidance literature:

With methanol; copper(l) iodide; In N,N-dimethyl-formamide; at 120 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tet.2012.05.127

upstream raw materials:

koenoline

1-methoxy-3-methylcarbazole

2-methoxy-4-methylaniline

methyl 3-methoxy-4-aminobenzoate

Downstream raw materials:

1-methoxy-3-methylcarbazole

koenoline

Refernces

• 1、 Avila-Melo, José Luis,Benavides, Adriana,Fuentes-Gutiérrez, Alfredo,Tamariz, Joaquín,Jiménez-Vázquez, Hugo A.. "Total Synthesis of the Natural Carbazoles O -Demethylmurrayanine and Murrastanine A, and of a C4,C4′ Symmetric Murrastanine A Dimer from N -Phenyl-4,5-dimethylene-1,3-oxazolidin-2-one". . p. 2201 - 2211. Retrieved 2021/03/15.
• 2、 Chakraborti, Gargi,Paladhi, Sushovan,Mandal, Tirtha,Dash, Jyotirmayee. ""on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols". . p. 7347 - 7359. Retrieved 2018/07/29.