Oroidin

Base Information

• Chemical Name: Oroidin
• CAS No.: 34649-22-4
• Molecular Formula: C11H11 Br2 N5 O
• Molecular Weight: 389.049
• Hs Code.: 2934999090
• UNII: PF75E92XKM
• DSSTox Substance ID: DTXSID001020635
• Nikkaji Number: J18.375J,J3.216.122G
• Wikipedia: Oroidin
• Wikidata: Q15425298
• Pharos Ligand ID: YDXJH4H7KYUN
• Metabolomics Workbench ID: 133475
• ChEMBL ID: CHEMBL397591
• Mol file: 34649-22-4.mol

Synonyms:7-(15)N-oroidin;oroidin

Chemical Property of Oroidin

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 100.32000
• Density: 1.948g/cm³
• LogP: 2.60920
• XLogP3: 2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 388.93099
• Heavy Atom Count: 19
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC(=C1Br)Br)C(=O)NCC=CC2=CN=C(N2)N
• Isomeric SMILES: C1=C(NC(=C1Br)Br)C(=O)NC/C=C/C2=CN=C(N2)N

Technology Process of Oroidin

There total 31 articles about Oroidin 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%

tert-butyl (E)-[4-(3-(4,5-dibromo-1H-pyrrole-2-carboxamido)prop-1-enyl)-1H-imidazol-2-yl]carbamate (917919-56-3) → oroidin (34649-22-4)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2010.05.074

Reference yield: 71.0%

(Z)-oroidin (269064-68-8) → oroidin (34649-22-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 50 ℃; for 2h;

DOI:10.1021/ol0608451

Reference yield: 65.0%

(E)-4,5-dibromo-N-(3-(imidazo[1,2-a]pyrimidin-2-yl)allyl)-1H-pyrrole-2-carboxamide (1443034-58-9) → oroidin (34649-22-4)

Guidance literature:

With hydrazine hydrate; at 20 ℃; for 0.5h;

DOI:10.1039/c3ob40668g

upstream raw materials:

(Z)-oroidin

tert-butyl (E)-[4-(3-(4,5-dibromo-1H-pyrrole-2-carboxamido)prop-1-enyl)-1H-imidazol-2-yl]carbamate

tert-butyl (E)-2-(tert-butoxycarbonylamino)-4-[3-(1,3-dioxoisoindolin-2-yl)prop-1-enyl]-1H-imidazol-1-carboxylate

tert-butyl (E)-[4-(3-aminoprop-1-enyl)-1H-imidazol-2-yl]carbamate

Refernces

• 1、 Olofson, Anne,Yakushijin, Kenichi,Horne, David A.. "Synthesis of Marine Sponge Alkaloids Oroidin, Clathrodin, and Dispacamides. Preparation and Transformation of 2-Amino-4,5-dialkoxy-4,5-dihydroimidazolines from 2-Aminoimidazoles". . p. 1248 - 1253. Retrieved 1998.
• 2、 Zidar, Nace,Montalv?o, Sofia,Hodnik, ?iga,Nawrot, Dorota A.,?ula, Ale?,Ila?, Janez,Kikelj, Danijel,Tammela, P?ivi,Ma?i?, Lucija Peterlin. "Antimicrobial activity of the marine alkaloids, clathrodin and oroidin, and their synthetic analogues". . p. 940 - 963. Retrieved 2014/03/21.