Curine

Base Information

• Chemical Name: Curine
• CAS No.: 436-05-5
• Deprecated CAS: 1398-06-7,1349-62-8,1414-38-6,30912-56-2,1414-38-6,30912-56-2,896437-99-3
• Molecular Formula: C36H38N2O6
• Molecular Weight: 594.708
• European Community (EC) Number: 207-109-4
• NSC Number: 77034
• UNII: 6037FRH2SX
• DSSTox Substance ID: DTXSID50893489
• Nikkaji Number: J38.782G
• Wikidata: Q27263150
• Metabolomics Workbench ID: 122484
• ChEMBL ID: CHEMBL1169627
• Mol file: 436-05-5.mol

Synonyms:curine

Chemical Property of Curine

Chemical Property:

• Vapor Pressure: 1.27E-20mmHg at 25°C
• Melting Point: 213°; mp 221° in vacuo; mp 161°
• Refractive Index: 1.619
• Boiling Point: 706.5 °C at 760 mmHg
• PKA: 9.39±0.20(Predicted)
• Flash Point: 381.1 °C
• PSA: 83.86000
• Density: 1.239 g/cm³
• LogP: 6.43220
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Very Slightly)
• 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:

≥98% ^*data from raw suppliers

l-Bebeerine(Curine) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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
• Uses: l-Bebeerine is a bisbenzylisoqinoline alkaloid which displays anto-allergic properties. In addition, has been shown to arrest cell cycle activity and induce apoptosis.

Technology Process of Curine

There total 41 articles about Curine 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:

1-methylisoquinoline

chondrofoline

3,4-Dihydroxybenzoic acid

4-methoxybenzoic acid