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CS-W001157 4
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Ethyl cyclopent-3-enecarboxylate

  • CAS No. 21622-01-5

  • Cat. No. CS-W014373
  • Purity≥97%
  • MDL No.MFCD06410819

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

Ethyl cyclopent-3-enecarboxylate|CS-W014373

Structure of 21622-01-5

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General Information

  • CAS No. 21622-01-5
  • Cat. No. CS-W014373
  • Purity ≥97%
  • MDL No. MFCD06410819
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₂O₂
  • Molecular Weight 140.18
  • Synonym(s) Ethyl-3-cyclopentene-1-carboxylate
  • SMILES CCOC(=O)C1CC=CC1

Description

Ethyl cyclopent-3-enecarboxylate features a conjugated enoate system with a rigid cyclopentene backbone, enabling efficient Diels-Alder cycloadditions. The ester functionality provides stability and facilitates downstream transformations. This reagent integrates readily into complex molecular architectures under mild conditions.

Application

Ethyl cyclopent-3-enecarboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted cyclopentane derivatives via Diels-Alder reactions and conjugate additions. Its enone functionality supports broad functional group tolerance and facilitates downstream transformations such as hydrogenation and electrophilic functionalization. The compound exhibits excellent bench stability and is readily purified by standard chromatographic methods, making it well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • Ethyl 2-allylpent-4-enoate|CS-0136294
      18325-74-1
    • ~96%
    • In-stock
      Ethyl cyclopent-3-enecarboxylate|CS-W014373
      21622-01-5

    References

    • Bespalova, N. B.; Bovina, M. A.; Sergeeva, M. B.; Zaikin, V. G. Russian Chemical Bulletin, 1994 , vol. 43, # 8 p. 1425 - 1426 Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1994 , # 8 p. 1503 - 1504
  • Route2
    • null|null
      64-17-5
    • In-stock
      Cyclopent-3-enecarboxylic acid|CS-W002373
      7686-77-3
    • ~91%
    • In-stock
      Ethyl cyclopent-3-enecarboxylate|CS-W014373
      21622-01-5

    References

    • Tarur, Venkatasubramanian Radhakrishnan; Sathe, Dhananjay Govind; Bhise, Nandu Baban; Sawant, Kamlesh Digambar; Naik, Tushar Anil; Srivastav, Neeraj; Deore, Raviraj Bhatu Patent: US2008/275241 A1, 2008 ; Location in patent: Page/Page column 10 ;
  • Route3
    • Diethyl cyclopent-3-ene-1,1-dicarboxylate|CS-W001503
      21622-00-4
    • ~%
    • In-stock
      Ethyl cyclopent-3-enecarboxylate|CS-W014373
      21622-01-5

    References

    • Journal of the American Chemical Society, , vol. 117, # 35 p. 8992 - 8998

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02
Signal Word : Danger
UN#: 3272
Class : 3
Packing Group : Ⅱ
Hazard Statements : H225
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P370+P378-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   1.5157
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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