(12S,16R)-7,10-Diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene

Base Information

• Chemical Name: (12S,16R)-7,10-Diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene
• CAS No.: 620948-93-8
• Molecular Formula: C₁₅H₂₀N₂
• Molecular Weight: 228.337
• DSSTox Substance ID: DTXSID80977680
• Mol file: 620948-93-8.mol

Synonyms:620948-93-8;(12S,16R)-7,10-Diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene;SCHEMBL5483166;DTXSID80977680

Chemical Property of (12S,16R)-7,10-Diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene

Chemical Property:

• PSA: 15.27000
• Density: 1.16
• LogP: 2.88730
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 228.162648646
• Heavy Atom Count: 17
• Complexity: 291

Purity/Quality:

98%Min ^*data from raw suppliers

Vabicaserin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CN3CCNCC4=C3C(=CC=C4)C2C1
• Isomeric SMILES: C1C[C@@H]2CN3CCNCC4=C3C(=CC=C4)[C@@H]2C1
• Uses: Vabicaserin is a potent 5-hydroxytryptamine 2C receptor full agonist which may be potentially used in the treatment of schizophrenia and other psychotic symptoms.

Technology Process of (12S,16R)-7,10-Diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene

There total 25 articles about (12S,16R)-7,10-Diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene 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: 70.0%

C20H28N2O2 → (±)-trans-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinoline (620948-93-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1055/s-0035-1562621

Reference yield: 60.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-((3aR,9bS)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]quinolin-5[9bH]-yl)ethanamine hydrochloride (1562204-36-7) → vabicaserin (620948-93-8)

Guidance literature:

With trifluoroacetic acid; In ethanol; water; at 20 ℃;

DOI:10.1021/jm401802f

Reference yield: 55.0%

C22H23N3O6S → vabicaserin (620948-93-8)

Guidance literature:

With C₁₆H₁₆NOPolS; potassium trimethylsilonate; In tetrahydrofuran; ethanol; at 20 ℃; for 4h; PS-Thiophenol

DOI:10.1002/chem.201802331

upstream raw materials:

formaldehyd

2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine

cyclopentene

5-Acetyl-4,5,6,7,9,9a,10,11,12,12a-decahydrocyclopenta[c][1,4]diazepino[6,7,1-ij]quinoline

Refernces

• 1、 Koolman, Hannes F.,Braje, Wilfried M.,Haupt, Andreas. "Synthesis of 4,4′-Disubstituted and Spiro-tetrahydroquinolines via Photochemical Cyclization of Acrylanilides and the First Synthesis of (±)- trans -Vabicaserin". . p. 2561 - 2566. Retrieved 2016/11/11.
• 2、 -. "CHIRAL SYNTHESIS OF DIAZEPINOQUINOLINES". Page/Page column 10. . Retrieved 2009/04/24.