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Methyl 3-oxocyclopentanecarboxylate

  • CAS No. 32811-75-9

  • Cat. No. CS-W019720
  • Molecule weight142.15
  • Purity≥95%
  • MDL No.MFCD09832106

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

Methyl 3-oxocyclopentanecarboxylate|CS-W019720

Structure of 32811-75-9

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General Information

  • CAS No. 32811-75-9
  • Cat. No. CS-W019720
  • Purity ≥95%
  • MDL No. MFCD09832106
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀O₃
  • Molecular Weight 142.15
  • Synonym(s) Methyl-3-oxocyclopentane carboxylate
  • SMILES O=C(C1CC(CC1)=O)OC

Description

Methyl 3-oxocyclopentanecarboxylate features a cyclopentane ring with strategically positioned carbonyl and ester groups, enabling seamless integration into cycloaddition and Michael addition reactions. This bench-stable ketone ester serves as a key intermediate in the synthesis of bioactive cyclic compounds and natural product analogs.

Application

Methyl 3-oxocyclopentanecarboxylate serves as a versatile synthon in organic synthesis, enabling efficient construction of cyclopentane-based scaffolds. Its α,β-unsaturated carbonyl system facilitates Michael additions, aldol reactions, and metal-catalyzed cyclizations. The ester group provides a handle for selective reduction or hydrolysis, while the ketone supports enolization and electrophilic functionalization. Bench-stable and readily purified by distillation or chromatography, it functions reliably in multi-step sequences for natural product and medicinal chemistry applications.

Synthesis

  • Route1

    References

    • Bristol-Myers Company Patent: US4272437 A1, 1981 ;
  • Route2

    References

    • Ranu, Brindaban C.; Dutta, Jyotirmoy; Guchhait, Sankar K. Organic Letters, 2001 , vol. 3, # 16 p. 2603 - 2605
  • Route3

    References

    • WO2010/107765 A1, ; Page/Page column 59 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS09
Signal Word : Danger
UN#: 3082
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H318-H411
Precautionary Statements : P264-P270-P273-P280-P305+P351+P338-P330-P391-P501

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   0.5286
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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