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2,3-Dihydro-1H-cyclopenta[a]naphthalen-1-one

  • CAS No. 6342-87-6

  • Cat. No. CS-0155976
  • Molecule weight182.22
  • Purity≥98%
  • MDL No.MFCD00466286

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

2,3-Dihydro-1H-cyclopenta[a]naphthalen-1-one|CS-0155976

Structure of 6342-87-6

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General Information

  • CAS No. 6342-87-6
  • Cat. No. CS-0155976
  • Purity ≥98%
  • MDL No. MFCD00466286
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₀O
  • Molecular Weight 182.22
  • Synonym(s) 2,3-Dihydro-1H-benz[E]inden-1-one
  • SMILES C1=CC=C2C(=C1)C=CC3=C2C(=O)CC3

Description

This bicyclic ketone features a rigid, fused-ring framework with defined stereochemical control points. The carbonyl group occupies a bridgehead position, enhancing reactivity in cycloaddition and reduction processes. Its planar geometry supports π-stacking interactions in supramolecular systems.

Application

2,3-Dihydro-1H-cyclopenta[a]naphthalen-1-one serves as a versatile polycyclic building block in synthetic organic chemistry, enabling efficient access to complex fused-ring architectures. Its ketone functionality facilitates nucleophilic additions and reductions, while the rigid, planar framework supports applications in medicinal chemistry and materials science. Bench-stable and compatible with standard purification methods, it functions effectively in multi-step syntheses requiring structural rigidity and defined stereochemical control.

Synthesis

  • Route1

    References

    • Kita; Higuchi; Yoshida; Iio; Kitagaki; Ueda; Akai; Fujioka Journal of the American Chemical Society, 2001 , vol. 123, # 14 p. 3214 - 3222
  • Route2

    References

    • FUJIFILM Corporation; SAKITA, Kyouhei; KIKUCHI, Wataru; YUMOTO, Masatoshi; HIKITA, Masanori Patent: US2013/171415 A1, 2013 ; Location in patent: Paragraph 0570; 0571; 0572 ;
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      27673-99-0
    • ~%
    • In-stock
      2,3-Dihydro-1H-cyclopenta[a]naphthalen-1-one|CS-0155976
      6342-87-6

    References

    • Hulin, Bernard; Koreeda, Masato Journal of Organic Chemistry, 1984 , vol. 49, # 1 p. 207 - 209

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   2.9687
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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