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CS-W001157 4
Total: USD 88.00

2-Azabicyclo[2.2.2]octan-3-one

  • CAS No. 3306-69-2

  • Cat. No. CS-0052042
  • Purity≥97%
  • MDL No.None

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

2-Azabicyclo[2.2.2]octan-3-one|CS-0052042

Structure of 3306-69-2

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General Information

  • CAS No. 3306-69-2
  • Cat. No. CS-0052042
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₁NO
  • Molecular Weight 125.17
  • Synonym(s) 2-azabicyclo
  • SMILES O=C1NC2CCC1CC2

Description

2-Azabicyclo[2.2.2]octan-3-one delivers a rigid, nitrogen-substituted cycloalkanone framework ideal for probing conformational constraints in medicinal chemistry. The bridgehead nitrogen imparts enhanced polarity and hydrogen-bonding capacity, while the ketone group serves as a versatile handle for selective derivatization under mild conditions. This scaffold supports efficient integration into bioactive molecules requiring defined three-dimensional architecture.

Application

2-Azabicyclo[2.2.2]octan-3-one serves as a conformationally constrained scaffold for medicinal chemistry, enabling the study of stereoregulated interactions in bioactive molecules. Its stable bicyclic structure features a ketone at C3 and a tertiary amine at N1, offering orthogonal reactivity for selective functionalization. The molecule exhibits excellent bench stability and facilitates efficient derivatization via enolate alkylation or reductive amination, making it a practical building block for targeted synthesis of nitrogen-containing heterocycles and drug-like compounds.

Synthesis

  • Route1

    References

    • Chung, John Y. L.; Ho, Guo-Jie Synthetic Communications, 2002 , vol. 32, # 13 p. 1985 - 1995
  • Route2

    References

    • Windhorst; Bechger; Visser; Menge; Leurs; Timmerman; Herscheid Journal of Fluorine Chemistry, 1996 , vol. 80, # 1 p. 35 - 40
  • Route3
    • 4-Aminobenzoic acid Conivaptan Impurity|CS-0213989
      150-13-0
    • ~%
    • In-stock
      2-Azabicyclo[2.2.2]octan-3-one|CS-0052042
      3306-69-2

    References

    • Houben; Pfau Chemische Berichte, 1916 , vol. 49, p. 2295

Safety Information

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

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Computational Chemistry Data

  • TPSA   29.1
  • LogP   0.675
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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