Bebeerine

Base Information

• Chemical Name: Bebeerine
• CAS No.: 477-60-1
• Molecular Formula: C₃₆H₃₈N₂O₆
• Molecular Weight: 594.708
• UNII: 01MDR0WU2J
• DSSTox Substance ID: DTXSID80963907
• Metabolomics Workbench ID: 70939
• Nikkaji Number: J3.078.619J
• Wikidata: Q27105192
• Mol file: 477-60-1.mol

Synonyms:bebeerine

Chemical Property of Bebeerine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 215℃
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 706.5°Cat760mmHg
• Flash Point: 381.1°C
• PSA: 83.86000
• Density: 1.239g/cm³
• LogP: 6.43220
• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 594.27298694
• Heavy Atom Count: 44
• Complexity: 948

Purity/Quality:

95%-98% ^*data from raw suppliers

BEBEERINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C6C(CC7=CC(=C(C=C7)O)O3)N(CCC6=CC(=C5O)OC)C)OC
• Isomeric SMILES: CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C6[C@H](CC7=CC(=C(C=C7)O)O3)N(CCC6=CC(=C5O)OC)C)OC

Technology Process of Bebeerine

There total 41 articles about Bebeerine 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:

4-hydroxy-3-iodo-benzaldehyde (60032-63-5) → (±)-tubocurine + (±)-curine (436-05-5,477-58-7,477-60-1,12578-01-7,26057-51-2,26279-95-8,31503-97-6)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium carbonate / ethanol / 5 h

2: sodium tetrahydroborate / ethanol / 20 °C

3: phosphorus tribromide / 0 - 20 °C

4: sodium tetrahydroborate; potassium hexamethylsilazane / methanol

5: pyridine; caesium carbonate; copper(I) bromide dimethylsulfide complex / 36.25 h / 20 - 135 °C / Molecular sieve; Inert atmosphere; Sealed tube

6: pyridine; caesium carbonate; copper(I) bromide dimethylsulfide complex / 288 h / 20 - 130 °C / Molecular sieve; Inert atmosphere; Sealed tube

7: boron tribromide / hexane; dichloromethane / 2 h / -19 °C

With pyridine; sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; boron tribromide; phosphorus tribromide; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; In methanol; ethanol; hexane; dichloromethane; 6: |Ullmann Condensation;

DOI:10.1021/acs.joc.6b02647

Reference yield:

C50H50N2O6 → (±)-tubocurine + (±)-curine (436-05-5,477-58-7,477-60-1,12578-01-7,26057-51-2,26279-95-8,31503-97-6)

Guidance literature:

With boron tribromide; In hexane; dichloromethane; at -19 ℃; for 2h; Overall yield = 72 %; Overall yield = 6.2 mg;

DOI:10.1021/acs.joc.6b02647

Reference yield:

vanillin (121-33-5,8014-42-4) → (±)-tubocurine + (±)-curine (436-05-5,477-58-7,477-60-1,12578-01-7,26057-51-2,26279-95-8,31503-97-6)

Guidance literature:

Multi-step reaction with 10 steps

1: bromine; acetic acid / 18 h / 0 - 20 °C

2: potassium carbonate / ethanol / 80 °C

3: borane-THF / tetrahydrofuran / 15 h / 20 °C

4: 42 h / 40 °C

5: potassium acetate; iodine / ethanol / 0.5 h / 20 °C

6: methanol / 20 °C

7: sodium tetrahydroborate; potassium hexamethylsilazane / methanol

8: pyridine; caesium carbonate; copper(I) bromide dimethylsulfide complex / 36.25 h / 20 - 135 °C / Molecular sieve; Inert atmosphere; Sealed tube

9: pyridine; caesium carbonate; copper(I) bromide dimethylsulfide complex / 288 h / 20 - 130 °C / Molecular sieve; Inert atmosphere; Sealed tube

10: boron tribromide / hexane; dichloromethane / 2 h / -19 °C

With pyridine; sodium tetrahydroborate; borane-THF; copper(I) bromide dimethylsulfide complex; bromine; iodine; potassium acetate; boron tribromide; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; acetic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 9: |Ullmann Condensation;

DOI:10.1021/acs.joc.6b02647

upstream raw materials:

4-(benzyloxy)-3-bromo-5-methoxybenzaldehyde

[4-(benzyloxy)-3-bromo-5-methoxyphenyl]methanol

β-<4-benzyloxy-5-bromo-3-methoxyphenyl>ethylamine

3-methoxy-4-(phenylmethoxy)benzaldehyde

Downstream raw materials:

4-methoxybenzoic acid