Roxindole

Base Information

• Chemical Name: Roxindole
• CAS No.: 112192-04-8
• Molecular Formula: C23H26 N2 O
• Molecular Weight: 346.472
• Hs Code.: 2933990090
• UNII: 43227SMS0O
• DSSTox Substance ID: DTXSID5043895
• Nikkaji Number: J395.967H
• Wikipedia: Roxindole
• Wikidata: Q7372445
• NCI Thesaurus Code: C90625
• Pharos Ligand ID: 7HFBTPGBF1KH
• Metabolomics Workbench ID: 57043
• ChEMBL ID: CHEMBL431367
• Mol file: 112192-04-8.mol

Synonyms:3-(4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)butyl)-1H-indol-5-ol;5-hydroxy-3-(4-(4-phenyl-1,2,3,6-tetrahydropyidyl)-1-butyl)-1-indole mesylate;EMD 49980;EMD-49980;roxindol;roxindole;roxindole hydrochloride;roxindole mesylate;roxindole monohydrochloride

Chemical Property of Roxindole

Chemical Property:

• Vapor Pressure: 7.46E-14mmHg at 25°C
• Boiling Point: 575.7°Cat760mmHg
• PKA: 10.15±0.40(Predicted)
• Flash Point: 302°C
• PSA: 39.26000
• Density: 1.173g/cm³
• LogP: 4.92340
• Storage Temp.: Desiccate at -20°C
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 346.204513457
• Heavy Atom Count: 26
• Complexity: 471

Purity/Quality:

98%Min ^*data from raw suppliers

Roxindole hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC=C1C2=CC=CC=C2)CCCCC3=CNC4=C3C=C(C=C4)O
• Uses: Roxindole Hydrochloride is a selective and potent presynaptic D-2 dopamine autoreceptor agonist.

Technology Process of Roxindole

There total 7 articles about Roxindole 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:

4-(5-methoxy-1H-indol-3-yl)butyric acid (83696-90-6) → roxindole (112192-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 1 h, 2.) THF, RT, overnight

2: dihydrobis(methoxyethanato-O,O')aluminate sodium / tetrahydrofuran / 2 h / Ambient temperature

3: diisobutylaluminium hydride (DIBAH) / toluene / 1.5 h / Heating

With diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; toluene;

DOI:10.1021/jm00100a006

Reference yield:

1,2,3,6-tetrahydro-4-phenylpyridine hydrochloride (43064-12-6) → roxindole (112192-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 1 h, 2.) THF, RT, overnight

2: dihydrobis(methoxyethanato-O,O')aluminate sodium / tetrahydrofuran / 2 h / Ambient temperature

3: diisobutylaluminium hydride (DIBAH) / toluene / 1.5 h / Heating

With diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; toluene;

DOI:10.1021/jm00100a006

Reference yield:

4-(5-Methoxy-1H-indol-3-yl)-1-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butan-1-one (143682-32-0) → roxindole (112192-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dihydrobis(methoxyethanato-O,O')aluminate sodium / tetrahydrofuran / 2 h / Ambient temperature

2: diisobutylaluminium hydride (DIBAH) / toluene / 1.5 h / Heating

With diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene;

DOI:10.1021/jm00100a006

upstream raw materials:

5-methoxy-3-[3-(1,2,3,6-tetrahydro-4-phenyl-1-pyridyl)butyl]indole

5-methoxylindole

4-(5-methoxy-indol-3-yl)-4-oxo-butyric acid

1-(5-methoxy-1H-indol-3-yl)-4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butane-1,4-dione

Refernces

• 1、 Bottcher,Barnickel,Hausberg,Haase,Seyfried,Eiermann. "Synthesis and dopaminergic activity of some 3-(1,2,3,6-tetrahydro-1- pyridylalkyl)indoles. A novel conformational model to explain structure- activity relationships". . p. 4020 - 4026. Retrieved 2007/10/02.