Phenserine

Base Information

• Chemical Name: Phenserine
• CAS No.: 101246-66-6
• Molecular Formula: C20H23 N3 O2
• Molecular Weight: 337.422
• European Community (EC) Number: 634-436-3
• UNII: SUE285UG3S,N8142NV8UM
• DSSTox Substance ID: DTXSID00906018
• Nikkaji Number: J562.416I
• Wikipedia: Phenserine
• Wikidata: Q27095557
• Pharos Ligand ID: BQSGQPKF9G81
• Metabolomics Workbench ID: 149322
• ChEMBL ID: CHEMBL74926
• Mol file: 101246-66-6.mol

Synonyms:N-phenylcarbamoyl eseroline;N-phenylcarbamoyleseroline;phenserine;posiphen

Chemical Property of Phenserine

Chemical Property:

• Vapor Pressure: 5.85E-09mmHg at 25°C
• Melting Point: 151-152 °C
• Boiling Point: 468.7°Cat760mmHg
• PKA: 13.05±0.70(Predicted)
• Flash Point: 237.3°C
• PSA: 44.81000
• Density: 1.228g/cm³
• LogP: 3.74250
• Storage Temp.: 2-8°C
• Solubility.: H2O:
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 337.17902698
• Heavy Atom Count: 25
• Complexity: 507

Purity/Quality:

98%Min ^*data from raw suppliers

Phenserine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC4=CC=CC=C4)C)C
• Isomeric SMILES: C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC4=CC=CC=C4)C)C
• Recent ClinicalTrials: Safety, Tolerability, PK and PD of Posiphen? in Subjects With Early Alzheimer's Disease
• Uses: Phenserine is inhibitor of amyloid precursor protein (APP). Used in Alzheimer’s treatments.

Technology Process of Phenserine

There total 17 articles about Phenserine 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: 20.0%

phenyl isocyanate (103-71-9) + eseroline (469-22-7) → phenserine (101246-66-6)

Guidance literature:

eseroline; With sodium; In diethyl ether; at 20 ℃; for 0.0333333h;

phenyl isocyanate; In diethyl ether; at 20 ℃; for 0.666667h;

DOI:10.1021/acscatal.0c00841

Reference yield:

(-)-esermethole (65166-97-4) → phenserine (101246-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BBr₃ / CH₂Cl₂ / 3 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 20 °C

2.2: 3.22 g / tetrahydrofuran / 4.5 h

With boron tribromide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja046690e

Reference yield:

(±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole (2731-01-3,65131-82-0,65166-97-4,104069-12-7) → phenserine + phenserine (101246-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1: boron tribromide / dichloromethane / 1.5 h / 23 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran / 14 h / 23 °C / Inert atmosphere

3: CHIRALPAK OJ-H (2 cm x 25 cm) / methanol; carbon dioxide; diethylamine / resolution of racemate; Supercritical conditions

With boron tribromide; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; carbon dioxide; diethylamine;

DOI:10.1021/jo202078z

upstream raw materials:

phenyl isocyanate

eseroline

(3S)-(5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetaldehyde

(-)-esermethole

Downstream raw materials:

Br^(1-)*C₂₁H₂₆N₃O₂⁽¹⁺⁾

Refernces

• 1、 Schammel, Alex W.,Chiou, Grace,Garg, Neil K.. "Synthesis of (+)-phenserine using an interrupted Fischer indolization reaction". . p. 725 - 728. Retrieved 2012/03/26.
• 2、 Huang, Audris,Kodanko, Jeremy J.,Overman, Larry E.. "Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine". . p. 14043 - 14053. Retrieved 2007/10/03.