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CS-W001157 4
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6,7,8,9-Tetrahydro-5H-benzo[7]annulen-5-one

  • CAS No. 826-73-3

  • Cat. No. CS-0070941
  • Purity≥97%
  • MDL No.None

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

6,7,8,9-Tetrahydro-5H-benzo[7]annulen-5-one|CS-0070941

Structure of 826-73-3

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General Information

  • CAS No. 826-73-3
  • Cat. No. CS-0070941
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₂O
  • Molecular Weight 160.21
  • Synonym(s) 6,7,8,9-Tetrahydro-5H-benzocyclohepten-5-one
  • SMILES O=C1C(C=CC=C2)=C2CCCC1

Description

6,7,8,9-Tetrahydro-5H-benzo[7]annulen-5-one features a strained, electron-rich annulene core with a ketone at the 5-position, enabling direct functionalization and integration into complex polycyclic frameworks. This scaffold offers enhanced stability under standard conditions while maintaining reactivity for transition-metal-catalyzed transformations.

Application

6,7,8,9-Tetrahydro-5H-benzo[7]annulen-5-one serves as a versatile bicyclic building block for synthesizing complex polycyclic architectures. Its ketone functionality enables standard enolate chemistry and nucleophilic additions, while the saturated ring system offers enhanced bench stability and predictable reactivity. This scaffold facilitates efficient access to fused heterocycles and natural product analogs through established synthetic transformations.

Synthesis

  • Route1

    References

    • Tamami, Bahman; Yeganeh, Hamid Tetrahedron, 1997 , vol. 53, # 23 p. 7889 - 7896
  • Route2

    References

    • Orita, Akihiro; Yaruva, Jayamma; Otera, Junzo Angewandte Chemie - International Edition, 1999 , vol. 38, # 15 p. 2267 - 2270
  • Route3
    • In-stock
      5-Phenylvaleric acid|CS-0076939
      2270-20-4
    • ~62%
    • null|null
      118514-42-4
    • In-stock
      6,7,8,9-Tetrahydro-5H-benzo[7]annulen-5-one|CS-0070941
      826-73-3

    References

    • Journal of Organic Chemistry, , vol. 54, # 5 p. 1144 - 1149

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

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   2.5957
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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