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CS-W001157 4
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Ethyl 2-cyclobutylideneacetate

  • CAS No. 27741-65-7

  • Cat. No. CS-0038534
  • Purity≥95%
  • MDL No.MFCD11977311

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

Ethyl 2-cyclobutylideneacetate|CS-0038534

Structure of 27741-65-7

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General Information

  • CAS No. 27741-65-7
  • Cat. No. CS-0038534
  • Purity ≥95%
  • MDL No. MFCD11977311
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₂O₂
  • Molecular Weight 140.18
  • Synonym(s) Ethyl2-cyclobutylideneacetate
  • SMILES CCOC(=O)C=C1CCC1

Description

Ethyl 2-cyclobutylideneacetate features a strained cyclobutylidene moiety flanked by an ester group, enabling its use in cycloaddition reactions and as a building block for complex carbocycles. The electron-deficient alkene facilitates Diels-Alder and [2+2] cycloadditions under mild conditions.

Application

Ethyl 2-cyclobutylideneacetate serves as a versatile Michael acceptor and dienophile in synthetic organic chemistry, enabling efficient construction of cyclohexene and cycloheptene scaffolds via Diels-Alder reactions. Its α,β-unsaturated ester functionality exhibits excellent bench stability and compatibility with diverse nucleophiles, facilitating straightforward functionalization and purification. This compound functions as a key building block for complex cyclic architectures in natural product synthesis and medicinal chemistry campaigns.

Synthesis

  • Route1
    • null|null
      1191-95-3
    • In-stock
      Ethyl (triphenylphosphoranylidene) acetate|CS-M0973
      1099-45-2
    • ~71%
    • In-stock
      Ethyl 2-cyclobutylideneacetate|CS-0038534
      27741-65-7

    References

    • US2012/295874 A1, ; Page/Page column 245 ; US 20120295874 A1
  • Route2
    • Ethyl (E)-6-bromohex-2-enoate|CS-0738464
      71032-10-5
    • ~48%
    • In-stock
      Ethyl 2-cyclobutylideneacetate|CS-0038534
      27741-65-7

    References

    • Journal of the American Chemical Society, , vol. 128, # 5 p. 1472 - 1473
  • Route3
    • In-stock
      Ethyl 2-(diethoxyphosphoryl)acetate  Ticagrelor Impuruity|CS-0167245
      867-13-0
    • null|null
      1191-95-3
    • ~80%
    • In-stock
      Ethyl 2-cyclobutylideneacetate|CS-0038534
      27741-65-7

    References

    • Journal of the Chemical Society. Perkin Transactions 2, , # 5 p. 937 - 945

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   26.3
  • LogP   1.6598
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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