Corybulbine

Base Information

• Chemical Name: Corybulbine
• CAS No.: 518-77-4
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.434
• UNII: 7P0E484I6E
• Nikkaji Number: J34.126F
• Mol file: 518-77-4.mol

Synonyms:Corybulbine;Corybulbin;518-77-4;UNII-7P0E484I6E;7P0E484I6E;13abeta-Berbin-3-ol, 2,9,10-trimethoxy-13alpha-methyl-;(+)-Corybulbine;D-CORYBULBINE;CORYDALIS-G;CORYBULBINE [MI];CORYBULBINE, (+)-;AKOS000278004;Q27268659;3-HYDROXY-13.ALPHA.-METHYL-2,9,10-TRIMETHOXY-13A.BETA.-BERBINE;(13S,13aR)-2,9,10-trimethoxy-13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-3-ol;6H-DIBENZO(A,G)QUINOLIZIN-3-OL, 5,8,13,13A-TETRAHYDRO-2,9,10-TRIMETHOXY-13-METHYL-, (13S,13AR)-

Chemical Property of Corybulbine

Chemical Property:

• Vapor Pressure: 1.48E-10mmHg at 25°C
• Melting Point: 242°
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 498.4°Cat760mmHg
• Flash Point: 255.2°C
• PSA: 51.16000
• Density: 1.26g/cm³
• LogP: 3.57240
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 355.17835828
• Heavy Atom Count: 26
• Complexity: 489

Purity/Quality:

98%min ^*data from raw suppliers

CORYBULBINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C3=CC(=C(C=C3CCN2CC4=C1C=CC(=C4OC)OC)O)OC
• Isomeric SMILES: C[C@@H]1[C@@H]2C3=CC(=C(C=C3CCN2CC4=C1C=CC(=C4OC)OC)O)OC

Technology Process of Corybulbine

There total 15 articles about Corybulbine 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: 90.0%

C28H29NO4 → corybulbine (518-77-4)

Guidance literature:

With palladium on activated carbon; hydrogen; In methanol; for 12h; under 760.051 Torr;

DOI:10.1021/acs.orglett.7b00414

Reference yield: 90.0%

C28H29NO4 → (+/-)-corybulbine (518-77-4,16562-09-7,27313-87-7,101541-43-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; for 12h; under 760.051 Torr;

DOI:10.1002/chem.201601245

Reference yield:

6-(Benzyloxy)-7-methoxy-1,2,3,4-tetrahydroisoquinoline (98809-69-9) → corybulbine (518-77-4)

Guidance literature:

Multi-step reaction with 4 steps

1: (S,R)-N-PINAP; copper(l) iodide; benzoic acid / toluene / 12 h / 40 °C / Inert atmosphere; Molecular sieve

2: potassium carbonate; methanol / 2 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium formate / N,N-dimethyl-formamide; water / 2 h / 100 °C / Inert atmosphere

4: hydrogen; palladium on activated carbon / methanol / 12 h / 760.05 Torr

With methanol; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (S,R)-N-PINAP; palladium on activated carbon; hydrogen; sodium formate; potassium carbonate; benzoic acid; In methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.orglett.7b00414

upstream raw materials:

6-(Benzyloxy)-7-methoxy-1,2,3,4-tetrahydroisoquinoline

6-bromo-2,3-dimethoxybenzaldehyde

Downstream raw materials:

dehydrocorybulbine

Refernces

• 1、 Zhou, Shiqiang,Tong, Rongbiao. "A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps". . p. 7084 - 7089. Retrieved 2016/05/19.