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CS-W001157 4
Total: USD 88.00

4-Oxoadamantane-1-carboxylic acid

  • CAS No. 56674-87-4

  • Cat. No. CS-W001595
  • Purity≥97%
  • MDL No.None

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

4-Oxoadamantane-1-carboxylic acid|CS-W001595

Structure of 56674-87-4

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General Information

  • CAS No. 56674-87-4
  • Cat. No. CS-W001595
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₄O₃
  • Molecular Weight 194.23
  • Synonym(s) 4-oxotricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid
  • SMILES OC([C@@]1(C[C@@H]2C[C@@H]3C1)C[C@@H](C3)C2=O)=O

Description

4-Oxoadamantane-1-carboxylic acid features a rigid, polycyclic adamantane core bearing a ketone at C4 and a carboxylic acid at C1, enabling versatile conjugation and integration into functional materials. The adjacent carbonyl group enhances electrophilicity for nucleophilic transformations, while the steric bulk imparts stability under standard reaction conditions.

Application

4-Oxoadamantane-1-carboxylic acid serves as a rigid, sterically defined building block for medicinal chemistry and materials science. Its cyclohexanone-like carbonyl at the 4-position enables standard enolate chemistry and nucleophilic additions, while the carboxylic acid facilitates amide coupling and salt formation. Bench-stable and readily purified by recrystallization, it functions effectively in multistep syntheses requiring structural rigidity and predictable reactivity.

Synthesis

  • Route1
    • Methyl 4-oxoadamantane-1-carboxylate|CS-W001596
      56674-88-5
    • ~86%
    • In-stock
      4-Oxoadamantane-1-carboxylic acid|CS-W001595
      56674-87-4

    References

    • BRISTOL-MYERS SQUIBB COMPANY; WROBLESKI, Stephen T.; BROWN, Gregory D.; DOWEYKO, Lidia M.; DUAN, Jingwu; GUO, Junqing; HYNES, John; JIANG, Bin; KEMPSON, James; LIN, Shuqun; LU, Zhonghui; SPERGEL, Steven, H.; TOKARSKI, John S.; WU, Hong; YANG, Bingwei Vera Patent: WO2012/125886 A1, 2012 ; Location in patent: Page/Page column 93 ; WO 2012/125886 A1
  • Route2
    • In-stock
      Idramantone|CS-4565
      20098-14-0
    • null|null
      64-18-6
    • ~85%
    • In-stock
      4-Oxoadamantane-1-carboxylic acid|CS-W001595
      56674-87-4

    References

    • Becker, Calvin L.; Engstrom, Kenneth M.; Kerdesky, Francis A.; Tolle, John C.; Wagaw, Seble H.; Wang, Weifeng Organic Process Research and Development, 2008 , vol. 12, # 6 p. 1114 - 1118
  • Route3
    • null|null
      38584-33-7
    • ~62%
    • In-stock
      4-Oxoadamantane-1-carboxylic acid|CS-W001595
      56674-87-4

    References

    • Manchand; Cerruti; Martin; Hill; Merrett; Keech; Belshe; Connell; Sim Journal of Medicinal Chemistry, 1990 , vol. 33, # 7 p. 1992 - 1995

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

Quality Control

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Computational Chemistry Data

  • TPSA   54.37
  • LogP   1.4664
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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