(+)-Condylocarpine

Base Information

• Chemical Name: (+)-Condylocarpine
• CAS No.: 4939-81-5
• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.407
• Nikkaji Number: J13.415E,J664.768E
• Wikidata: Q104397658
• Mol file: 4939-81-5.mol

Synonyms:isocondylocarpine;condylocarpine

Chemical Property of (+)-Condylocarpine

Chemical Property:

• PSA: 41.57000
• LogP: 2.90700
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 322.168127949
• Heavy Atom Count: 24
• Complexity: 652

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1C2CCN3C1C4(CC3)C5=CC=CC=C5NC4=C2C(=O)OC
• Isomeric SMILES: C/C=C\1/[C@@H]2CCN3[C@H]1[C@]4(CC3)C5=CC=CC=C5NC4=C2C(=O)OC

Technology Process of (+)-Condylocarpine

There total 10 articles about (+)-Condylocarpine 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:

stemmadenine → condylocarpine (4939-81-5)

Guidance literature:

With oxygen; platinum; In ethyl acetate; for 4h;

Reference yield:

C18H18N2O3 (1260095-48-4) + ethyltriphenylphosphonium bromide (1530-32-1) → (+)-isocondylocarpine (1260095-53-1) + condylocarpine (4939-81-5)

Guidance literature:

ethyltriphenylphosphonium bromide; With n-butyllithium; In toluene; at 20 ℃; for 1h; Inert atmosphere;

C₁₈H₁₈N₂O₃; In tetrahydrofuran; toluene; at 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/ol102709s

Reference yield:

(1S,5R)-2-(tert-butoxycarbonyl)-6,6-(di-tert-butoxycarbonyl)-1,2,3,4,5,6-hexahydro-l,5-methanoazocino[4,3-b]indole-12-one (1218950-54-9) → (+)-isocondylocarpine (1260095-53-1) + condylocarpine (4939-81-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: water / 13 h / 20 °C

3.1: thionyl chloride / 2.5 h / 50 °C / Inert atmosphere

3.2: 0.5 h / Inert atmosphere

4.1: methanol / 20 h / 20 °C / Inert atmosphere

4.2: 20 °C / pH 3 - 5 / Inert atmosphere

4.3: Inert atmosphere

5.1: dichloromethane / 1 h / Inert atmosphere; Molecular sieve

5.2: 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

6.1: Raney nickel / tetrahydrofuran; water / 1 h / 50 °C / Inert atmosphere

7.1: acetic anhydride / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

8.1: n-butyllithium / toluene / 1 h / 20 °C / Inert atmosphere

8.2: 3.5 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; n-butyllithium; thionyl chloride; acetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; 7.1: Albright-Goldman oxidation / 8.2: Wittig reaction;

DOI:10.1021/ol102709s

upstream raw materials:

Condylocarpin-N_b-oxid

(1S,5R)-2-(tert-butoxycarbonyl)-6,6-(di-tert-butoxycarbonyl)-1,2,3,4,5,6-hexahydro-l,5-methanoazocino[4,3-b]indole-12-one

C₂₉H₄₀N₂O₇

C₂HF₃O₂*C₁₅H₁₆N₂O₃

Downstream raw materials:

tubotaiwine