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CS-W001157 4
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Spiro[5.5]undecan-2-one

  • CAS No. 1781-81-3

  • Cat. No. CS-0139727
  • Molecule weight166.26
  • Purity≥98%
  • MDL No.None

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

Spiro[5.5]undecan-2-one|CS-0139727

Structure of 1781-81-3

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General Information

  • CAS No. 1781-81-3
  • Cat. No. CS-0139727
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₈O
  • Molecular Weight 166.26
  • Synonym(s) undecan-8-one
  • SMILES O=C1CC2(CCCCC2)CCC1

Description

Spiro[5.5]undecan-2-one features a rigid, three-dimensional spirocyclic core that imparts exceptional stereochemical stability. This scaffold integrates a ketone functionality at the spiro junction, enabling direct use in asymmetric synthesis and as a building block for complex natural product analogs. The molecule's defined geometry facilitates predictable reactivity in transition-metal-catalyzed transformations and offers enhanced solubility in polar aprotic solvents.

Application

Spiro[5.5]undecan-2-one serves as a rigid, bicyclic scaffold enabling stereocontrolled synthesis of complex polycyclic architectures. Its spirocyclic core exhibits excellent bench stability and functions as a versatile building block in medicinal chemistry, particularly for constructing bioactive heterocycles and constrained molecular frameworks through selective functionalization at the ketone position.

Synthesis

  • Route1
    • null|null
      62788-58-3
    • ~51%
    • In-stock
      Spiro[5.5]undecan-2-one|CS-0139727
      1781-81-3

    References

    • Ruppert, John F.; White, James D. Journal of the American Chemical Society, 1981 , vol. 103, # 7 p. 1808 - 1813
  • Route2
    • null|null
      1781-80-2
    • ~%
    • In-stock
      Spiro[5.5]undecan-2-one|CS-0139727
      1781-81-3

    References

    • de Jongh,H.A.P.; Wynberg,H. Tetrahedron, 1964 , vol. 20, p. 2553 - 2573
  • Route3
    • In-stock
      3-Chlorocyclohex-2-enone|CS-0180958
      5682-75-7
    • null|null
      2223-58-7
    • ~74%
    • In-stock
      Spiro[5.5]undecan-2-one|CS-0139727
      1781-81-3

    References

    • Wender, Paul A.; White, Alan W. Journal of the American Chemical Society, 1988 , vol. 110, # 7 p. 2218 - 2223

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-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   3.08
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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