Stevensine

Base Information

• Chemical Name: Stevensine
• CAS No.: 99102-22-4
• Molecular Formula: C11H9Br2N5O
• Molecular Weight: 387.03
• UNII: 44PB7HEQ22
• DSSTox Substance ID: DTXSID50451503
• Nikkaji Number: J332.238F
• Wikipedia: Stevensine
• Wikidata: Q15427846
• Metabolomics Workbench ID: 136470
• ChEMBL ID: CHEMBL464097
• Mol file: 99102-22-4.mol

Synonyms:stevensine;99102-22-4;Odiline;44PB7HEQ22;4-(2-amino-1H-imidazol-5-yl)-2,3-dibromo-6,7-dihydro-1H-pyrrolo[2,3-c]azepin-8-one;UNII-44PB7HEQ22;4-(2-Amino-1H-imidazol-5-yl)-2,3-dibromo-6,7-dihydropyrrolo(2,3-C)azepin-8(1H)-one;Pyrrolo(2,3-C)azepin-8(1H)-one, 4-(2-amino-1H-imidazol-4-yl)-2,3-dibromo-6,7-dihydro-;Pyrrolo(2,3-C)azepin-8(1H)-one, 4-(2-amino-1H-imidazol-5-yl)-2,3-dibromo-6,7-dihydro-;CHEMBL464097;DTXSID50451503;ZNIBKSGUBSYKLY-UHFFFAOYSA-N;Q15427846

Chemical Property of Stevensine

Chemical Property:

• PSA: 100.32000
• LogP: 2.27900
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 386.91534
• Heavy Atom Count: 19
• Complexity: 418

Purity/Quality:

99% ^*data from raw suppliers

Stevensine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=C(C2=C(C(=O)N1)NC(=C2Br)Br)C3=CN=C(N3)N
• Uses: Stevensine is a dibrominated alkaloid deterrant of predatory fishes.

Technology Process of Stevensine

There total 2 articles about Stevensine 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: 40.0%

4-(2-Amino-5-bromo-1H-imidazol-4-yl)-2,3-dibromo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one (184887-85-2) → Stevensine/odiline (99102-22-4) + (-)-hymenine (154569-13-8,105748-62-7)

Guidance literature:

With methanesulfonic acid; at 90 ℃; for 24h; unsealed flask;

DOI:10.1016/0040-4039(96)01888-6

Reference yield:

(-)-hymenine (154569-13-8,105748-62-7) → Stevensine/odiline (99102-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Br₂ / trifluoroacetic acid

2: 20 percent / methanesulfonic acid / 24 h / 90 °C / unsealed flask

With methanesulfonic acid; bromine; In trifluoroacetic acid;

DOI:10.1016/0040-4039(96)01888-6

upstream raw materials:

4-(2-Amino-5-bromo-1H-imidazol-4-yl)-2,3-dibromo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one

(-)-hymenine

Refernces