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CS-W001157 4
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(3aR,4S,7R,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

  • CAS No. 6118-51-0

  • Cat. No. CS-W014305
  • Purity≥95%
  • MDL No.MFCD00151506

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

(3aR,4S,7R,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione|CS-W014305

Structure of 6118-51-0

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General Information

  • CAS No. 6118-51-0
  • Cat. No. CS-W014305
  • Purity ≥95%
  • MDL No. MFCD00151506
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆O₄
  • Molecular Weight 166.13
  • Synonym(s) 7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic Anhydride
  • SMILES O=C1OC([C@@]2([H])[C@](O3)([H])C=C[C@]3([H])[C@]21[H])=O

Description

This tetrahydroepoxyisobenzofuran-1,3-dione features a rigid, fused bicyclic core with defined stereochemistry at four chiral centers. The epoxy bridge imparts high reactivity for ring-opening transformations, while the electron-deficient dione moiety enables efficient Diels-Alder cycloadditions. Bench-stable and moisture-tolerant, it serves as a key building block in complex natural product synthesis and asymmetric catalysis.

Application

(3aR,4S,7R,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione serves as a versatile bicyclic building block for the synthesis of complex heterocyclic systems. Its fused epoxide and quinone motif enables controlled ring-opening reactions and Diels–Alder cycloadditions, offering access to functionalized scaffolds relevant in natural product and medicinal chemistry. Bench-stable and compatible with standard purification protocols, it facilitates efficient, multi-step synthetic sequences.

Synthesis

  • Route1
    • null|null
      110-00-9
    • null|null
      108-31-6
    • ~98%
    • In-stock
      (3aR,4S,7R,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione|CS-W014305
      6118-51-0

    References

    • Tetrahedron Letters, , vol. 49, # 39 p. 5680 - 5682
  • Route2
    • null|null
      110-00-9
    • null|null
      108-31-6
    • ~%
    • In-stock
      (3aR,4S,7R,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione|CS-W014305
      6118-51-0
    • null|null
      6766-44-5

    References

    • Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), , vol. 38, # 11.1 p. 2303 - 2308 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, , # 11 p. 2510 - 2517
  • Route3
    • null|null
      110-00-9
    • null|null
      108-31-6
    • ~68%
    • In-stock
      (3aR,4S,7R,7aS)-rel-3a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione|CS-W014305
      6118-51-0
    • In-stock
      Maleic acid|CS-0015079
      110-16-7

    References

    • Green Chemistry, , vol. 16, # 1 p. 167 - 175

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   -0.3606
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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