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CS-W001157 4
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Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate

  • CAS No. 50388-51-7

  • Cat. No. CS-0146427
  • Purity≥95%
  • MDL No.MFCD09869052

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

Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate|CS-0146427

Structure of 50388-51-7

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General Information

  • CAS No. 50388-51-7
  • Cat. No. CS-0146427
  • Purity ≥95%
  • MDL No. MFCD09869052
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₆O₃
  • Molecular Weight 184.23
  • Synonym(s) Methyl 5,5-Dimethyl-2-oxocyclohexanecarboxylate
  • SMILES O=C(C1C(CCC(C)(C)C1)=O)OC

Description

Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate features a sterically hindered cyclohexanone core with a methyl ester group, enabling controlled reactivity in synthetic transformations. The geminal dimethyl substitution enhances stability and modulates electrophilicity at the carbonyl center. This compound serves as a key building block for complex cyclic architectures in natural product synthesis and medicinal chemistry applications.

Application

Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized cyclohexane scaffolds. The molecule's gem-dimethyl substitution enhances steric shielding and bench stability, while the α,β-unsaturated ketone motif facilitates Michael additions, aldol reactions, and enolate-mediated transformations. Its methyl ester group supports straightforward derivatization, making it valuable for constructing complex carbocyclic systems in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • In-stock
      4,4-Dimethylcyclohexanone|CS-W002564
      4255-62-3
    • null|null
      616-38-6
    • ~92%
    • In-stock
      Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate|CS-0146427
      50388-51-7

    References

    • Madder, Annemieke; De Clercq, Pierre J.; Declercq, Jean-Paul Journal of Organic Chemistry, 1998 , vol. 63, # 8 p. 2548 - 2559
  • Route2

    References

    • Strunz, George M.; Bethell, Richard; Dumas, Michael T.; Boyonoski, Nick Canadian Journal of Chemistry, 1997 , vol. 75, # 6 p. 742 - 753
  • Route3
    • null|null
      54815-28-0
    • ~%
    • In-stock
      Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate|CS-0146427
      50388-51-7

    References

    • Tschudi; Schinz Helvetica Chimica Acta, 1950 , vol. 33, p. 1865,1869

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   1.5548
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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