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3-Cyclopentyl-3-oxopropanenitrile

  • CAS No. 95882-33-0

  • Cat. No. CS-0053864
  • Purity≥98%
  • MDL No.None

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

3-Cyclopentyl-3-oxopropanenitrile|CS-0053864

Structure of 95882-33-0

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General Information

  • CAS No. 95882-33-0
  • Cat. No. CS-0053864
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁NO
  • Molecular Weight 137.18
  • Synonym(s) Cyclopentanepropanenitrile, b-oxo-
  • SMILES N#CCC(C1CCCC1)=O

Description

3-Cyclopentyl-3-oxopropanenitrile features a cyclopentyl group flanked by a nitrile and ketone functionality, enabling direct incorporation into heterocyclic scaffolds. This bifunctional electrophile facilitates efficient cyclization reactions under mild conditions, delivering complex nitrogen-containing rings with high regioselectivity. The molecule exhibits favorable stability and solubility in common organic solvents, simplifying handling during synthetic workflows.

Application

3-Cyclopentyl-3-oxopropanenitrile serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to pyrrolidine and piperidine scaffolds via cyclization reactions. Its α,β-unsaturated nitrile functionality facilitates Michael additions and condensations under mild conditions. The molecule exhibits good bench stability and compatibility with common protecting groups, simplifying purification and integration into multi-step sequences. Functions effectively in the construction of nitrogen-containing ring systems relevant to medicinal chemistry and process-scale applications.

Synthesis

  • Route1
    • In-stock
      Methyl cyclopentanecarboxylate|CS-W005310
      4630-80-2
    • null|null
      75-05-8
    • ~93%
    • In-stock
      3-Cyclopentyl-3-oxopropanenitrile|CS-0053864
      95882-33-0

    References

    • Rowbottom, Martin W.; Faraoni, Raffaella; Chao, Qi; Campbell, Brian T.; Lai, Andiliy G.; Setti, Eduardo; Ezawa, Maiko; Sprankle, Kelly G.; Abraham, Sunny; Tran, Lan; Struss, Brian; Gibney, Michael; Armstrong, Robert C.; Gunawardane, Ruwanthi N.; Nepomuceno, Ronald R.; Valenta, Ianina; Hua, Helen; Gardner, Michael F.; Cramer, Merryl D.; Gitnick, Dana; Insko, Darren E.; Apuy, Julius L.; Jones-Bolin, Susan; Ghose, Arup K.; Herbertz, Torsten; Ator, Mark A.; Dorsey, Bruce D.; Ruggeri, Bruce; Williams, Michael; Bhagwat, Shripad; James, Joyce; Holladay, Mark W. Journal of Medicinal Chemistry, 2012 , vol. 55, # 3 p. 1082 - 1105
  • Route2
    • In-stock
      Ethyl cyclopentanecarboxylate|CS-0235375
      5453-85-0
    • null|null
      75-05-8
    • ~99%
    • In-stock
      3-Cyclopentyl-3-oxopropanenitrile|CS-0053864
      95882-33-0

    References

    • European Molecular Biology Laboratory; F. Hoffmann-La Roche AG; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SAUVAITRE, Thibault; SIMON, Céline; MORICE, Christophe; GIETHLEN, Bruno; LANGER, Thierry; SMITH, Mark; SO, Sung-Sau; CLASSEN-HOUBEN, Dirk; BUSCHMANN, Helmut Patent: US2013/317022 A1, 2013 ; Location in patent: Paragraph 0542-0544 ;
  • Route3

    References

    • US2008/4302 A1, ; Page/Page column 52-53 ; US 20080004302 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3276
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   40.86
  • LogP   1.65938
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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