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7-Benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one

  • CAS No. 77716-01-9

  • Cat. No. CS-W000408
  • Molecule weight231.29
  • Purity≥97%
  • MDL No.None

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

7-Benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one|CS-W000408

Structure of 77716-01-9

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General Information

  • CAS No. 77716-01-9
  • Cat. No. CS-W000408
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₇NO₂
  • Molecular Weight 231.29
  • Synonym(s) 7-Benzyl-3-oxo-7-aza-bicyclo[3.3.1nonan-9-one
  • SMILES O=C1C2CN(CC1COC2)CC3=CC=CC=C3

Description

7-Benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one features a rigid, electron-deficient bicyclic scaffold that enables precise spatial control in synthetic transformations. The benzyl group enhances lipophilicity and facilitates downstream functionalization, while the lactam moiety offers stability under standard conditions. This structure serves as a strategic intermediate in complex molecule assembly.

Application

7-Benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one serves as a versatile scaffold for medicinal chemistry campaigns, enabling efficient access to constrained heterocyclic architectures. Its bicyclic core combines a benzylic handle with a ketone and ether functionalities, supporting diverse transformations including reductive amination, nucleophilic addition, and transition-metal-catalyzed coupling. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis in drug discovery programs.

Synthesis

  • Route1
    • In-stock
      Tetrahydro-4H-pyran-4-one|CS-D0601
      29943-42-8
    • null|null
      50-00-0
    • null|null
      2182-52-7
    • ~72%
    • In-stock
      7-Benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one|CS-W000408
      77716-01-9

    References

    • Arjunan, Palanisamy; Berlin, K. Darrell; Barnes, Charles L.; Helm, Dick van der Journal of Organic Chemistry, 1981 , vol. 46, # 16 p. 3196 - 3204
  • Route2
    • In-stock
      Tetrahydro-4H-pyran-4-one|CS-D0601
      29943-42-8
    • null|null
      50-00-0
    • null|null
      64-19-7
    • null|null
      100-46-9
    • ~60%
    • In-stock
      7-Benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one|CS-W000408
      77716-01-9

    References

    • LUPIN LIMITED; THOTAPALLY, Rajesh; PATHAK, Ashok, Bhau; KARDILE, Bhavana, Shrirang; SINDKHEDKAR, Milind, Dattatraya; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar Patent: WO2012/25811 A1, 2012 ; Location in patent: Page/Page column 53-54 ; WO 2012/025811 A1
  • Route3
    • In-stock
      Tetrahydro-4H-pyran-4-one|CS-D0601
      29943-42-8
    • null|null
      100-46-9
    • ~87%
    • In-stock
      7-Benzyl-3-oxa-7-azabicyclo[3.3.1]nonan-9-one|CS-W000408
      77716-01-9

    References

    • Nippon Soda Co., Ltd. Patent: WO2007/40282 A1, 2007 ; Location in patent: Page/Page column 40-41 ;

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   29.54
  • LogP   1.3339
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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