Cas no 91147-07-8 (methyl 3-(9H-beta-carbolin-1-yl)propanoate)

methyl 3-(9H-beta-carbolin-1-yl)propanoate structure
91147-07-8 structure
Product Name:methyl 3-(9H-beta-carbolin-1-yl)propanoate
CAS No:91147-07-8
MF:C15H14N2O2
MW:254.283863544464
CID:1967957
PubChem ID:5319542
Update Time:2024-03-01

methyl 3-(9H-beta-carbolin-1-yl)propanoate Chemical and Physical Properties

Names and Identifiers

    • Infractine
    • methyl 3-(9H-beta-carbolin-1-yl)propanoate
    • 9H-Pyrido[3,4-b]indole-1-propanoic acid, methyl ester
    • Infractin
    • Methyl 9H-pyrido[3,4-b]indole-1-propanoate (ACI)
    • Kumujanrine
    • AKOS040734103
    • 91147-07-8
    • methyl 3-(9H-pyrido[3,4-b]indol-1-yl)propanoate
    • Methyl 3-(9H-pyrido(3,4-b)indol-1-yl)propanoate
    • FS-7954
    • DTXSID40238426
    • CHEBI:222843
    • Inchi: 1S/C15H14N2O2/c1-19-14(18)7-6-13-15-11(8-9-16-13)10-4-2-3-5-12(10)17-15/h2-5,8-9,17H,6-7H2,1H3
    • InChI Key: IYWBIIGDWQBZJQ-UHFFFAOYSA-N
    • SMILES: O=C(CCC1C2=C(C3C(N2)=CC=CC=3)C=CN=1)OC

Computed Properties

  • Exact Mass: 254.10600
  • Monoisotopic Mass: 254.105527694g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 4
  • Complexity: 334
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.4
  • Topological Polar Surface Area: 55?2

Experimental Properties

  • Color/Form: Cryst.
  • PSA: 54.98000
  • LogP: 2.82170

methyl 3-(9H-beta-carbolin-1-yl)propanoate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium ,  Carbon Solvents: Methanol
Reference
β-Carboline alkaloids. Part 6. Total synthesis of the phosphodiesterase inhibitor infractine
Bracher, F.; Hildebrand, D., Pharmazie, 1995, 50(3), 182-3

Production Method 2

Reaction Conditions
1.1 Reagents: Sulfuric acid Solvents: Methanol ;  24 h, reflux; reflux → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 8
Reference
Synthesis of Alkyl-Substituted Pyridines by Directed Pd(II)-Catalyzed C-H Activation of Alkanoic Amides
Hu, Peng; Bach, Thorsten, Synlett, 2015, 26(20), 2853-2857

Production Method 3

Reaction Conditions
Reference
Synthesis of manzamine C, infractine and 6-hydroxyinfractine
Nowak, Wolfgang; Gerlach, Hans, Liebigs Annalen der Chemie, 1993, (2), 153-9

Production Method 4

Reaction Conditions
1.1 Reagents: 2-Chloropyridine ,  Trifluoromethanesulfonic anhydride Solvents: Dichloromethane ;  1 min, -78 °C; 5 min, -78 °C; 5 min, -78 °C → 0 °C; 0 °C → rt; 3 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
Reference
Solution Phase and Nanoparticular Biosynthetically Inspired Interconnections in the Canthin-6-one β-Carboline Series and Study of Phenotypic Properties on C. elegans
Cebrian-Torrejon, Gerardo; Mackiewicz, Nicolas; Vazquez-Manrique, Rafael P.; Fournet, Alain; Figadere, Bruno; et al, European Journal of Organic Chemistry, 2013, 2013(26), 5821-5828

methyl 3-(9H-beta-carbolin-1-yl)propanoate Raw materials

methyl 3-(9H-beta-carbolin-1-yl)propanoate Preparation Products

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