Dizocilpine

Base Information

• Chemical Name: Dizocilpine
• CAS No.: 77086-21-6
• Molecular Formula: C16H15N
• Molecular Weight: 221.302
• Hs Code.: 2925290090
• UNII: 7PY8KH681I
• DSSTox Substance ID: DTXSID3048447
• Nikkaji Number: J246.194C
• Wikipedia: Dizocilpine
• Wikidata: Q4386371
• NCI Thesaurus Code: C65450
• Pharos Ligand ID: HD9SPGR82144
• Metabolomics Workbench ID: 68344
• ChEMBL ID: CHEMBL284237
• Mol file: 77086-21-6.mol

Synonyms:Dizocilpine;Dizocilpine Maleate;MK 801;MK-801;MK801

Chemical Property of Dizocilpine

Chemical Property:

• Vapor Pressure: 0.000321mmHg at 25°C
• Melting Point: 68.5-69°
• Boiling Point: 320.3°C at 760 mmHg
• PKA: 7.96±0.40(Predicted)
• Flash Point: 152.6°C
• PSA: 12.03000
• Density: 1.144g/cm³
• LogP: 3.47930
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 221.120449483
• Heavy Atom Count: 17
• Complexity: 313

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C3=CC=CC=C3CC(N1)C4=CC=CC=C24
• Isomeric SMILES: C[C@@]12C3=CC=CC=C3C[C@@H](N1)C4=CC=CC=C24
• Uses: Neuroprotective.

Technology Process of Dizocilpine

There total 12 articles about Dizocilpine 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: 97.0%

C21H24N2 (124070-25-3) → (+/-)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (70449-94-4,77086-18-1,77086-19-2,77086-21-6)

Guidance literature:

With potassium hydroxide; In ethylene glycol; at 150 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)95276-6

Reference yield: 85.0%

(5S,10R)-(+)-5-(bromomethyl)-10,11-dihydro-5H-dibenzo-[a,d]-cyclohepten-5,10-imine (159170-13-5) → Dizocilpine (77086-21-6)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 60 ℃; for 3h;

DOI:10.1021/ja016935c

Reference yield: 83.0%

5-methyl-12-((trifluoromethyl)sulfonyl)-10,11-dihydro-5H-5,10-epiminodibenzo[7]annulene → (+/-)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (70449-94-4,77086-18-1,77086-19-2,77086-21-6)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 0 - 50 ℃; for 14h; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201901673

upstream raw materials:

(5S,10R)-(+)-5-(bromomethyl)-10,11-dihydro-5H-dibenzo-[a,d]-cyclohepten-5,10-imine

(5S,10R)-(+)-5-(hydroxymethyl)-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5,10-imine

(5S,10R)-(+)-N-carboxylic acid vinyl ester-5-cyano-10,11-dihydro-5H-dibenzo[a,d]-cyclopenten-5,10-imine

C₂₁H₂₄N₂

Downstream raw materials:

(5S,10R)-(+)-3-bromo-10,11-dihydro-5-methyl-5H-dibenzocyclohepten-5,10-imine

Refernces

• 1、 Funabashi,Ratni,Kanai,Shibasaki. "Enantioselective construction of quaternary stereocenter through a reissert-type reaction catalyzed by an electronically tuned bifunctional catalyst: Efficient synthesis of various biologically significant compounds [24]". . p. 10784 - 10785. Retrieved 2007/10/03.