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CS-W001157 4
Total: USD 88.00

4-Hydroxy-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one

  • CAS No. 55618-81-0

  • Cat. No. CS-0099223
  • Purity≥95%
  • MDL No.MFCD09908208

*For research and further manufacturing use only, not for direct human use.

4-Hydroxy-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one|CS-0099223

Structure of 55618-81-0

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General Information

  • CAS No. 55618-81-0
  • Cat. No. CS-0099223
  • Purity ≥95%
  • MDL No. MFCD09908208
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉NO₂
  • Molecular Weight 151.16
  • Synonym(s) 4-Hydroxy-6,7-dihydro-1H-cyclopenta[b]pyridin-2(5H)-one
  • SMILES O=C1C=C(O)C(CCC2)=C2N1

Description

4-Hydroxy-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one features a fused bicyclic core with a hydroxyl group at the 4-position, enhancing polarity and hydrogen-bonding capacity. This scaffold offers stability under standard conditions and serves as a key building block in medicinal chemistry for targeted heterocyclic synthesis.

Application

4-Hydroxy-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one serves as a versatile heterocyclic building block in medicinal chemistry, offering a rigid, polar scaffold with defined hydrogen-bonding capacity. The hydroxyl group enables direct derivatization via esterification or ether formation, while the enolizable carbonyl supports nucleophilic addition and metal-catalyzed coupling reactions. Its stability under standard reaction conditions and compatibility with common protecting groups facilitate efficient synthesis of complex molecular architectures.

Synthesis

  • Route1
    • null|null
      25115-61-1
    • In-stock
      Diphenyl malonate|CS-0156092
      1969-44-4
    • ~48%
    • In-stock
      4-Hydroxy-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one|CS-0099223
      55618-81-0

    References

    • PFIZER LIMITED Patent: US2007/197478 A1, 2007 ; Location in patent: Page/Page column 67 ;
  • Route2
    • 4-Amino-5h,6h,7h-cyclopenta[b]pyridin-2-ol|CS-0239828
      63704-54-1
    • ~%
    • In-stock
      4-Hydroxy-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one|CS-0099223
      55618-81-0

    References

    • Journal of the American Chemical Society, , vol. 71, p. 2205,2207
  • Route3
    • Ethyl 4-hydroxy-2-oxo-2,5,6,7-tetrahydro-1h-cyclopenta[b]pyridine-3-carboxylate|CS-0667420
      55618-82-1
    • ~%
    • In-stock
      4-Hydroxy-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one|CS-0099223
      55618-81-0

    References

    • Helvetica Chimica Acta, , vol. 28, p. 1684,1690

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   53.09
  • LogP   0.5692
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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