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CS-W001157 4
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3-Oxocyclohexanecarboxylic acid

  • CAS No. 16205-98-4

  • Cat. No. CS-0044016
  • Purity≥95%
  • MDL No.MFCD01320172

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

3-Oxocyclohexanecarboxylic acid|CS-0044016

Structure of 16205-98-4

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General Information

  • CAS No. 16205-98-4
  • Cat. No. CS-0044016
  • Purity ≥95%
  • MDL No. MFCD01320172
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀O₃
  • Molecular Weight 142.15
  • Synonym(s) O**3-OXO-1-CYCLOHEXANECARBOXYLIC ACID
  • SMILES OC(=O)C1CCCC(=O)C1

Description

3-Oxocyclohexanecarboxylic acid features a conjugated keto-carboxylic acid motif within a cyclohexane ring, enabling direct participation in Michael additions and decarboxylation cascades. The α,β-unsaturated system facilitates efficient coupling with nucleophiles under mild conditions, while the cyclic scaffold imparts rigidity that enhances regioselectivity in synthetic transformations. This compound serves as a key intermediate for bioactive heterocycles and natural product analogs.

Application

3-Oxocyclohexanecarboxylic acid serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized cyclohexane scaffolds. Its α,β-unsaturated carbonyl system facilitates Michael additions, aldol reactions, and cyclizations under mild conditions. The molecule exhibits bench stability, ease of purification, and compatibility with common protecting groups, making it valuable for medicinal chemistry and natural product synthesis workflows.

Synthesis

  • Route1

    References

    • NIMBUS IRIS, INC.; ROMERO, Donna L.; ROBINSON, Shaughnessy; WESSEL, Matthew David; GREENWOOD, Jeremy Robert Patent: WO2014/11902 A1, 2014 ; Location in patent: Paragraph 00282-00283 ;
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 130, # 19 p. 6072 - 6073
  • Route3
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      10265-39-1
    • ~62%
    • In-stock
      3-Oxocyclohexanecarboxylic acid|CS-0044016
      16205-98-4

    References

    • Marchand, Alan P.; Sharma, Rajiv; Zope, Umesh R.; Watson, William H.; Kashyap, Ram P. Journal of Organic Chemistry, 1993 , vol. 58, # 3 p. 759 - 762

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   54.37
  • LogP   0.8303
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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