Arborinine

Base Information

• Chemical Name: Arborinine
• CAS No.: 5489-57-6
• Molecular Formula: C₁₆H₁₅NO₄
• Molecular Weight: 285.299
• Hs Code.: 2933990090
• UNII: 16XG8UE639
• ChEMBL ID: CHEMBL349609
• DSSTox Substance ID: DTXSID60203378
• Metabolomics Workbench ID: 44235
• Nikkaji Number: J13.628J
• NSC Number: 681020,94650
• Wikidata: Q27105822
• Mol file: 5489-57-6.mol

Synonyms:arborinine

Chemical Property of Arborinine

Chemical Property:

• Vapor Pressure: 5.85E-11mmHg at 25°C
• Melting Point: 177-177.5 °C
• Boiling Point: 508.4°C at 760 mmHg
• PKA: 7.29±0.20(Predicted)
• Flash Point: 261.3°C
• PSA: 60.69000
• Density: 1.296g/cm³
• LogP: 2.41450
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 285.10010796
• Heavy Atom Count: 21
• Complexity: 402

Purity/Quality:

Analysis control,98.5% ^*data from raw suppliers

Arborinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=O)C3=C(C(=C(C=C31)OC)OC)O

Technology Process of Arborinine

There total 16 articles about Arborinine 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: 84.0%

1,2,3-Trimethoxy-N-methylacridon (13082-16-1) → arborinine (5489-57-6)

Guidance literature:

With hydrogenchloride; In methanol; water; for 12h; Reflux;

DOI:10.1002/chem.201203859

Reference yield:

methyl iodide (74-88-4) → 1,2,3-Trimethoxy-N-methylacridon (13082-16-1) + arborinine (5489-57-6)

Guidance literature:

With potassium carbonate; acetone;

Reference yield:

3,4,5-Trimethoxyaniline (24313-88-0) → arborinine (5489-57-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper(I) oxide; copper; potassium carbonate / diethylene glycol dimethyl ether / 5 h / Reflux

2.1: Eaton's reagent / 0.83 h / 80 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / ethanol; water / 12 h / Reflux

With copper(I) oxide; hydrogenchloride; Eaton's reagent; copper; sodium hydride; potassium carbonate; In tetrahydrofuran; ethanol; diethylene glycol dimethyl ether; water; mineral oil; 1.1: Ullmann condensation;

DOI:10.1016/j.bmcl.2011.04.127

upstream raw materials:

1,2-dihydroxy-3-methoxy-10-methyl-9-acridone

dimethyl sulfate

1,2,3-Trimethoxy-N-methylacridon

methyl iodide

Refernces

• 1、 Bera, Sourav Sekhar,Sk, Md Raja,Maji, Modhu Sudan. "Weakly Coordinating, Ketone-Directed (η5-Pentamethylcyclopentadienyl)cobalt(III)- and (η5-Pentamethylcyclopentadienyl)rhodium(III)-Catalyzed C?H Amidation of Arenes: A Route to Acridone Alkaloids". supporting information. p. 1806 - 1811. Retrieved 2019/01/14.
• 2、 Pal, Chinmay,Kundu, Milan Kumar,Bandyopadhyay, Uday,Adhikari, Susanta. "Synthesis of novel heme-interacting acridone derivatives to prevent free heme-mediated protein oxidation and degradation". supporting information; experimental part. p. 3563 - 3567. Retrieved 2011/08/06.