Isocorybulbine

Base Information

• Chemical Name: Isocorybulbine
• CAS No.: 22672-74-8
• Molecular Formula: C21H25NO4
• Molecular Weight: 355.434
• UNII: 13DPT1YOCY
• Nikkaji Number: J34.166E
• Wikidata: Q27251509
• Mol file: 22672-74-8.mol

Synonyms:Isocorybulbine;(+)-Isocorybulbine;Isocorybulbine [MI];Isocorybulbine, (+)-;UNII-13DPT1YOCY;13DPT1YOCY;22672-74-8;6H-Dibenzo(a,g)quinolizin-2-ol, 5,8,13,13a-tetrahydro-3,9,10-trimethoxy-13-methyl-, (13S,13aR)-;13abeta-Berbin-2-ol, 3,9,10-trimethoxy-13alpha-methyl-;SCHEMBL679696;AKOS000277670;Q27251509;13A.BETA.-BERBIN-2-OL, 3,9,10-TRIMETHOXY-13.ALPHA.-METHYL-

Chemical Property of Isocorybulbine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 179-180°; also given as 187-188°
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 498.406°C at 760 mmHg
• PKA: 10.18±0.40(Predicted)
• Flash Point: 255.227°C
• PSA: 51.16000
• Density: 1.268g/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:

99% ^*data from raw 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)OC)O
• Isomeric SMILES: C[C@@H]1[C@@H]2C3=CC(=C(C=C3CCN2CC4=C1C=CC(=C4OC)OC)OC)O
• Description: This alkaloid, isomeric with corybulbine (q.v.) is present in Corydalis tuberosa D.C. and may be purified from EtOH when it yields colourless, flat leaflets which are only slightly soluble in EtOH. The base is dextrorotatory with [α]29Dl>s + 301° (CHC13). It furnishes a crystalline methiodide, m.p. 218-221 0c.

Technology Process of Isocorybulbine

There total 11 articles about Isocorybulbine 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: 91.0%

C28H29NO4 → Isocorybulbine (22672-74-8)

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 → isocorybulbine (478-31-9,22672-74-8,27313-92-4,38969-53-8)

Guidance literature:

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

DOI:10.1002/chem.201601245

Reference yield:

7-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (15357-95-6) → Isocorybulbine (22672-74-8)

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:

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

6-bromo-2,3-dimethoxybenzaldehyde

Downstream raw materials:

3,4-dimethoxy-phthalic acid

4-ethoxy-5-methoxy-phthalic acid