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Methyl 3-cyclobutyl-3-oxopropanoate

  • CAS No. 137638-05-2

  • Cat. No. CS-0049100
  • Purity≥96%
  • MDL No.MFCD11974606

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

Methyl 3-cyclobutyl-3-oxopropanoate|CS-0049100

Structure of 137638-05-2

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General Information

  • CAS No. 137638-05-2
  • Cat. No. CS-0049100
  • Purity ≥96%
  • MDL No. MFCD11974606
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₂O₃
  • Molecular Weight 156.18
  • Synonym(s) Cyclobutanepropanoic acid, β-oxo-, methyl ester
  • SMILES COC(=O)CC(=O)C1CCC1

Description

Methyl 3-cyclobutyl-3-oxopropanoate features a cyclobutyl group flanking a β-keto ester motif, delivering enhanced stability and reactivity in synthetic transformations. This bench-stable compound integrates readily into complex molecular architectures, particularly in the construction of strained ring systems and functionalized heterocycles under standard conditions.

Application

Methyl 3-cyclobutyl-3-oxopropanoate serves as a versatile building block for cyclobutane-containing scaffolds, enabling efficient access to functionalized heterocycles via Michael additions and aldol-type condensations. The α,β-unsaturated ester functionality facilitates conjugate addition reactions with amines, thiols, and carbon nucleophiles, while the cyclobutyl ring imparts conformational rigidity beneficial in medicinal chemistry. Bench-stable and readily purified by flash chromatography, it functions as a practical intermediate in complex molecule synthesis.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      Meldrum's acid|CS-D1154
      2033-24-1
    • null|null
      5006-22-4
    • ~75%
    • In-stock
      Methyl 3-cyclobutyl-3-oxopropanoate|CS-0049100
      137638-05-2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 17, # 24 p. 6836 - 6840
  • Route2
    • In-stock
      Meldrum's acid|CS-D1154
      2033-24-1
    • null|null
      5006-22-4
    • ~%
    • In-stock
      Methyl 3-cyclobutyl-3-oxopropanoate|CS-0049100
      137638-05-2

    References

    • WO2006/15842 A1, ; Page/Page column 34 ; WO 2006/015842 A1
  • Route3
    • null|null
      67-56-1
    • null|null
      134302-13-9
    • ~%
    • In-stock
      Methyl 3-cyclobutyl-3-oxopropanoate|CS-0049100
      137638-05-2

    References

    • WO2010/120854 A1, ; Page/Page column 124 ; WO 2010/120854 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P210-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P403-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   0.9187
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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