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CS-W001157 4
Total: USD 88.00

Bicyclo[2.2.1]Hept-5-en-2-one

  • CAS No. 694-98-4

  • Cat. No. CS-0480105
  • Purity≥97%
  • MDL No.MFCD00101751

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

Bicyclo[2.2.1]Hept-5-en-2-one|CS-0480105

Structure of 694-98-4

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General Information

  • CAS No. 694-98-4
  • Cat. No. CS-0480105
  • Purity ≥97%
  • MDL No. MFCD00101751
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈O
  • Molecular Weight 108.14
  • Synonym(s) norborn-5-en-2-one
  • SMILES O=C1C2CC(C=C2)C1

Description

Bicyclo[2.2.1]hept-5-en-2-one is a strained, electron-deficient enone scaffold featuring a conjugated double bond and ketone functionality within a rigid bicyclic framework. This structural motif enables participation in Diels-Alder reactions and serves as a key intermediate in synthetic routes to complex natural products and pharmaceuticals.

Application

Bicyclo[2.2.1]hept-5-en-2-one serves as a versatile synthetic building block in organic synthesis, leveraging its strained cyclohexadienone framework for Diels-Alder reactions and Michael additions. The enone functionality enables efficient conjugate addition and cyclization cascades, while the rigid bicyclic scaffold provides stereocontrol in complex molecule assembly. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step syntheses of natural products and pharmaceutical intermediates.

Synthesis

  • Route1
    • 2-Chlorobicyclo[2.2.1]hept-5-ene-2-carbonitrile|CS-0212734
      6945-87-5
    • ~91%
    • In-stock
      Bicyclo[2.2.1]Hept-5-en-2-one|CS-0480105
      694-98-4

    References

    • Drian, Claude Le; Greene, Andrew E. Journal of the American Chemical Society, 1982 , vol. 104, # 20 p. 5473 - 5483
  • Route2
    • null|null
      694-97-3
    • ~87%
    • In-stock
      Bicyclo[2.2.1]Hept-5-en-2-one|CS-0480105
      694-98-4

    References

    • Saunders, Martin; Jarret, Ronald M.; Pramanik, Pradip Journal of the American Chemical Society, 1987 , vol. 109, # 12 p. 3735 - 3739
  • Route3
    • null|null
      2890-98-4
    • ~86%
    • In-stock
      Bicyclo[2.2.1]Hept-5-en-2-one|CS-0480105
      694-98-4

    References

    • Fischer, Walter; Grob, Cyril A.; Sprecher, Georg von; Waldner, Adrian Helvetica Chimica Acta, 1980 , vol. 63, # 4 p. 816 - 823

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P370+P378-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   1.1515
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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