5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione

Base Information

• Chemical Name: 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
• CAS No.: 192820-78-3
• Molecular Formula: C18H16N2O6
• Molecular Weight: 356.335
• European Community (EC) Number: 803-124-0
• UNII: 1XI90I177M
• ChEMBL ID: CHEMBL357217
• DSSTox Substance ID: DTXSID20172879
• Metabolomics Workbench ID: 146987
• Nikkaji Number: J1.528.383A
• Pharos Ligand ID: J617VCV2LQ6F
• Wikidata: Q27093401
• Mol file: 192820-78-3.mol

Synonyms:5-methoxy-1,2-dimethyl-3-((4-nitrophenoxy)methyl)indole-4,7-dione;ES936 cpd

Chemical Property of 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione

Chemical Property:

• Melting Point: 227-288 °C
• Boiling Point: 623.9±55.0 °C(Predicted)
• PKA: -11.69±0.40(Predicted)
• PSA: 103.35000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 3.25320
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble2mg/mL (clear solution, warmed)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 356.10083623
• Heavy Atom Count: 26
• Complexity: 620

Purity/Quality:

99% ^*data from raw suppliers

ES 936 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C2=C(N1C)C(=O)C=C(C2=O)OC)COC3=CC=C(C=C3)[N+](=O)[O-]
• Uses: ES 936 is a NAD(P)H:quinone oxidoreductase inhibitor.

Technology Process of 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione

There total 3 articles about 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione 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: 57.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione (161518-24-7) → 5-methoxy-1m2-dimethyl-3-[(4-nitrophenoxy)methyl]-1H-indole-4,7-dione (192820-78-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 50 ℃;

DOI:10.1021/jm980328r

Reference yield:

5-Methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester (205177-88-4) → 5-methoxy-1m2-dimethyl-3-[(4-nitrophenoxy)methyl]-1H-indole-4,7-dione (192820-78-3)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. sodium dithionite / ethanol; CHCl₃

2: 1.) DIBAL, 2.) FeCl₃, aq. HCl / 1.) CH₂Cl₂, -30 deg C, 2 h, 2.) CH₂Cl₂, -30 deg C

3: 57 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 50 °C

With hydrogenchloride; sodium dithionite; iron(III) chloride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; chloroform;

DOI:10.1021/jm980328r

Reference yield:

ethyl 4,7-dihydroxy-5-methoxy-1,2-dimethylindole-3-carboxylate → 5-methoxy-1m2-dimethyl-3-[(4-nitrophenoxy)methyl]-1H-indole-4,7-dione (192820-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DIBAL, 2.) FeCl₃, aq. HCl / 1.) CH₂Cl₂, -30 deg C, 2 h, 2.) CH₂Cl₂, -30 deg C

2: 57 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 50 °C

With hydrogenchloride; iron(III) chloride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jm980328r

upstream raw materials:

4-nitro-phenol

3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione

5-Methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indole-3-carboxylic acid ethyl ester

Downstream raw materials:

4-nitro-phenol

3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione

Refernces