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CS-W001157 4
Total: USD 88.00

methyl 1-(Methoxycarbonyl)cyclopent-3-enecarboxylate

  • CAS No. 84646-68-4

  • Cat. No. CS-0061802
  • Purity≥95%
  • MDL No.None

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

methyl 1-(Methoxycarbonyl)cyclopent-3-enecarboxylate|CS-0061802

Structure of 84646-68-4

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General Information

  • CAS No. 84646-68-4
  • Cat. No. CS-0061802
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₂O₄
  • Molecular Weight 184.19
  • Synonym(s) Dimethyl 3-cyclopentene-1,1-dicarboxylate
  • SMILES COC(=O)C1(CC=CC1)C(=O)OC

Description

Methyl 1-(methoxycarbonyl)cyclopent-3-enecarboxylate features a conjugated enone system flanked by ester and cyclopentenyl moieties, enabling direct participation in Diels-Alder reactions. This strained, electron-deficient dienophile integrates efficiently into complex carbocyclic frameworks under mild conditions.

Application

Methyl 1-(methoxycarbonyl)cyclopent-3-enecarboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized cyclopentane scaffolds. The conjugated enoate system facilitates Michael additions and Diels-Alder reactions, while the ester group supports selective transformations under standard conditions. Its bench-stable nature and compatibility with diverse reaction protocols make it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      35357-77-8
    • ~95%
    • In-stock
      methyl 1-(Methoxycarbonyl)cyclopent-3-enecarboxylate|CS-0061802
      84646-68-4

    References

    • Oliveira, Caio C.; Dos Santos, Emerson A. F.; Bormio Nunes, Julia H.; Correia, Carlos Roque D. Journal of Organic Chemistry, 2012 , vol. 77, # 18 p. 8182 - 8190,9
  • Route2
    • null|null
      591-87-7
    • In-stock
      Dimethyl malonate|CS-0019394
      108-59-8
    • ~73%
    • In-stock
      methyl 1-(Methoxycarbonyl)cyclopent-3-enecarboxylate|CS-0061802
      84646-68-4

    References

    • Kammerer, Claire; Prestat, Guillaume; Gaillard, Thomas; Madec, David; Poli, Giovanni Organic Letters, 2008 , vol. 10, # 3 p. 405 - 408
  • Route3
    • null|null
      1476-11-5
    • In-stock
      Dimethyl malonate|CS-0019394
      108-59-8
    • ~10%
    • In-stock
      methyl 1-(Methoxycarbonyl)cyclopent-3-enecarboxylate|CS-0061802
      84646-68-4

    References

    • Broggi, Julie; Joubert, Nicolas; Diez-Gonzalez, Silvia; Berteina-Raboin, Sabine; Zevaco, Thomas; Nolan, Steven P.; Agrofoglio, Luigi A. Tetrahedron, 2009 , vol. 65, # 6 p. 1162 - 1170

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   52.6
  • LogP   0.6688
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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