Kopsinine

Base Information

• Chemical Name: Kopsinine
• CAS No.: 559-51-3
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.45
• DSSTox Substance ID: DTXSID30971299
• Nikkaji Number: J13.194F
• Wikipedia: Kopsinine
• Wikidata: Q105122807
• ChEMBL ID: CHEMBL4790316
• Mol file: 559-51-3.mol

Synonyms:kopsinine;kopsinine dihydrochloride, (2alpha,3beta,5alpha)-isomer

Chemical Property of Kopsinine

Chemical Property:

• Vapor Pressure: 4.95E-10mmHg at 25°C
• Boiling Point: 497.4°Cat760mmHg
• Flash Point: 254.6°C
• Density: 1.29g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 338.199428076
• Heavy Atom Count: 25
• Complexity: 623

Purity/Quality:

98.5% ^*data from raw suppliers

KOPSININE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CC23CCCN4C2C5(C1(CC3)NC6=CC=CC=C65)CC4
• Isomeric SMILES: COC(=O)[C@@H]1C[C@]23CCCN4[C@@H]2[C@@]5([C@]1(CC3)NC6=CC=CC=C65)CC4
• Description: Present in Kopsia longijlora, this base is purified by crystallization from light petroleum when it forms colourless crystals. It has [α]23D - 76.9° (c 2.09, CHC1 3). It forms a crystalline dihydrochloride with m.p. 253-4°C, a mono_x0002_methiodide, m.p. 265-6°C and a monopicrate, m.p. 222-3°C. The N-formyl derivative is identical with aspidofractine (q.v.).

Technology Process of Kopsinine

There total 22 articles about Kopsinine 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: 83.0%

C34H34N2O4S (1320267-57-9) → kopsinine (559-51-3,28161-78-6,98737-06-5,98759-78-5)

Guidance literature:

With Raney Ni; In ethanol; at 78 ℃;

DOI:10.1038/nature10232

Reference yield:

C27H28N2O3 (1320267-61-5) → kopsinine (559-51-3,28161-78-6,98737-06-5,98759-78-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trimethylsilyl iodide; triethylamine / dichloromethane / 0 °C

1.2: 40 °C

1.3: 0 °C

2.1: triethylamine / toluene / -45 - 23 °C

2.2: -30 - 23 °C

2.3: 0 °C

3.1: benzene / 100 °C

4.1: Raney Ni / ethanol / 78 °C

With trimethylsilyl iodide; triethylamine; In ethanol; dichloromethane; toluene; benzene;

DOI:10.1038/nature10232

Reference yield:

C24H22N2 → kopsinine (559-51-3,28161-78-6,98737-06-5,98759-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / toluene / -45 - 23 °C

1.2: -30 - 23 °C

1.3: 0 °C

2.1: benzene / 100 °C

3.1: Raney Ni / ethanol / 78 °C

With triethylamine; In ethanol; toluene; benzene;

DOI:10.1038/nature10232

upstream raw materials:

C₂₁H₂₄N₂O₂S

5-oxokopsinic acid

C₂₇H₂₈N₂O₃

C₂₆H₂₆N₂O₂

Refernces

• 1、 Jones, Spencer B.,Simmons, Bryon,Mastracchio, Anthony,MacMillan, David W. C.. "Collective synthesis of natural products by means of organocascade catalysis". . p. 183 - 188. Retrieved 2012/05/20.