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CS-W001157 4
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cis-Tetrahydropentalene-2,5(1H,3H)-dione

  • CAS No. 51716-63-3

  • Cat. No. CS-0046040
  • Purity≥98%
  • MDL No.MFCD00003771

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

cis-Tetrahydropentalene-2,5(1H,3H)-dione|CS-0046040

Structure of 51716-63-3

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General Information

  • CAS No. 51716-63-3
  • Cat. No. CS-0046040
  • Purity ≥98%
  • MDL No. MFCD00003771
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀O₂
  • Molecular Weight 138.16
  • Synonym(s) Tetrahydro-2,5(1H,3H)-pentalenedione
  • SMILES O=C(C[C@@]1([H])C2)C[C@]1([H])CC2=O

Description

cis-Tetrahydropentalene-2,5(1H,3H)-dione features a rigid, fused bicyclic framework with two ketone groups in close proximity, enabling selective reactivity in cycloaddition and Diels-Alder processes. The cis configuration enhances molecular polarity and facilitates controlled transformations under mild conditions. This scaffold serves as a valuable building block for complex heterocycles and natural product analogs.

Application

cis-Tetrahydropentalene-2,5(1H,3H)-dione serves as a valuable bicyclic synthon in synthetic organic chemistry, offering defined stereochemistry and dual carbonyl functionality for Diels-Alder reactions and heterocycle construction. Its bench-stable nature and predictable reactivity facilitate efficient access to complex polycyclic frameworks relevant to natural product synthesis and medicinal chemistry scaffolds.

Synthesis

  • Route1
    • null|null
      58648-36-5
    • ~80%
    • In-stock
      cis-Tetrahydropentalene-2,5(1H,3H)-dione|CS-0046040
      51716-63-3

    References

    • SHANGHAI HENGRUI PHARMACEUTICAL CO., LTD.; JIANGSU HENGRUI MEDICINE CO., LTD. Patent: US2012/184543 A1, 2012 ; Location in patent: Page/Page column 46 ;
  • Route2
    • null|null
      92007-38-0
    • ~99%
    • In-stock
      cis-Tetrahydropentalene-2,5(1H,3H)-dione|CS-0046040
      51716-63-3

    References

    • Harrowven, David C; Lucas, Matthew C; Howes, Peter D Tetrahedron, 2001 , vol. 57, # 44 p. 9157 - 9162
  • Route3
    • null|null
      82416-02-2
    • ~90%
    • In-stock
      cis-Tetrahydropentalene-2,5(1H,3H)-dione|CS-0046040
      51716-63-3

    References

    • Bertz, Steven H.; Rihs, G.; Woodward, R.B. Tetrahedron, 1982 , vol. 38, # 1 p. 63 - 70

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

Quality Control

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Computational Chemistry Data

  • TPSA   34.14
  • LogP   0.9446
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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