Kopsine

Base Information

• Chemical Name: Kopsine
• CAS No.: 559-48-8
• Molecular Formula: C22H24N2O4
• Molecular Weight: 380.437
• UNII: 9999HLB81M
• Wikidata: Q27272188
• Mol file: 559-48-8.mol

Synonyms:kopsine

Chemical Property of Kopsine

Chemical Property:

• Vapor Pressure: 3E-14mmHg at 25°C
• Melting Point: 220°C (dec.).
• Boiling Point: 579°Cat760mmHg
• Flash Point: 304°C
• PSA: 70.08000
• Density: 1.51g/cm³
• LogP: 1.84440
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 380.17360725
• Heavy Atom Count: 28
• Complexity: 816

Purity/Quality:

KOPSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)N1C2=CC=CC=C2C34C15CCC67C3N(CCC6)CC4C(=O)C5(C7)O
• Isomeric SMILES: COC(=O)N1C2=CC=CC=C2[C@@]34[C@]15CC[C@]67[C@@H]3N(CCC6)C[C@@H]4C(=O)[C@@]5(C7)O
• Description: The major constituent of Kopsia !ruticosa, this base has [α]D - 17.5° (c 2.15, CHC13). It forms a series of crystalline salts and derivatives, e.g. the aurichloride, m.p. 203-5°C (dec.); perchlorate, m.p. 284°C (dec.); picrate, m.p. 230°C (dec.) and methiodide, m.p. 200°C (dec.). It may be reduced to the dihydro derivative which has m.p. 218°C. When fused with NaOH the alkaloid furnishes 2- methylindole and 2-indole-2-carboxylic acid.

Technology Process of Kopsine

There total 7 articles about Kopsine 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:

1-Carbomethoxy-3-decarbomethoxy-10-oxokopsininecarbinol (122312-57-6) → (+/-)-Kopsine (559-48-8,122332-20-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) tri-n-butylphosphine, o-nitrophenyl selenocyanate, 2.) 50percent aq. H₂O₂ / 1.) THF, 20 deg C, 2 h, 2.) 20 deg C, 1 h

2: 92 percent / osmium tetraoxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 10 h / 25 °C

3: 1.) dimethylsulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) 5 min

4: 91 percent / lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

5: 1.) BH₃*THF, 2.) 5M HCl / 1.) THF, 40 min, 25 deg C, 2.) 60 deg C, 30 min

6: 1.) dimethylsulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) 5 min

With hydrogenchloride; osmium(VIII) oxide; ortho-nitrophenyl selenocyanate; borane-THF; oxalyl dichloride; tributylphosphine; dihydrogen peroxide; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1021/ja00199a033

Reference yield:

C22H24N2O3 (122294-95-5) → (+/-)-Kopsine (559-48-8,122332-20-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / osmium tetraoxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 10 h / 25 °C

2: 1.) dimethylsulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) 5 min

3: 91 percent / lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

4: 1.) BH₃*THF, 2.) 5M HCl / 1.) THF, 40 min, 25 deg C, 2.) 60 deg C, 30 min

5: 1.) dimethylsulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) 5 min

With hydrogenchloride; osmium(VIII) oxide; borane-THF; oxalyl dichloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1021/ja00199a033

Reference yield:

1-Carbomethoxy-10-oxo-3-hydroxykopsinine carboxaldehyde (122294-97-7) → (+/-)-Kopsine (559-48-8,122332-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

2: 1.) BH₃*THF, 2.) 5M HCl / 1.) THF, 40 min, 25 deg C, 2.) 60 deg C, 30 min

3: 1.) dimethylsulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) 5 min

With hydrogenchloride; borane-THF; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/ja00199a033

upstream raw materials:

22-Dihydrokopsine

1-Carbomethoxy-3-decarbomethoxy-10-oxokopsininecarbinol

C₂₂H₂₄N₂O₃

1-Carbomethoxy-10-oxo-3-hydroxykopsinine carboxaldehyde