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Rac-(3ar,6as)-hexahydro-1h-cyclopenta[c]furan-1,3-dione, cis

  • CAS No. 35878-28-5

  • Cat. No. CS-0215478
  • Purity≥97%
  • MDL No.None

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

Rac-(3ar,6as)-hexahydro-1h-cyclopenta[c]furan-1,3-dione, cis|CS-0215478

Structure of 35878-28-5

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General Information

  • CAS No. 35878-28-5
  • Cat. No. CS-0215478
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈O₃
  • Molecular Weight 140.14
  • Synonym(s) CYCLOPENTANE-1,2-DICARBOXYLIC ACID ANHYDRIDE
  • SMILES C1C[C@H]2[C@@H](C1)C(=O)OC2=O

Description

Rac-(3ar,6as)-hexahydro-1h-cyclopenta[c]furan-1,3-dione, cis features a rigid, fused bicyclic framework with complementary stereocenters enabling selective reactivity in asymmetric synthesis. This bench-stable, moisture-tolerant diketone integrates readily into complex molecular architectures through controlled reduction or cycloaddition processes.

Application

Rac-(3ar,6as)-hexahydro-1h-cyclopenta[c]furan-1,3-dione, cis serves as a versatile bicyclic building block in synthetic organic chemistry, enabling efficient access to complex polycyclic frameworks. Its rigid, saturated core exhibits excellent bench stability and functional group tolerance, facilitating downstream transformations including nucleophilic additions and selective reductions. The molecule functions as a key intermediate in the synthesis of bioactive heterocycles and natural product analogs, particularly in medicinal chemistry workflows requiring stereocontrolled ring formation.

Synthesis

  • Route1

    References

    • MEDIVIR AB; AYESA, Susana; BELDA, Oscar; BJÖRKLUND, Catarina; NILSSON, Magnus; RUSSO, Francesco; SAHLBERG, Christer; WIKTELIUS, Daniel Patent: WO2013/95275 A1, 2013 ; Location in patent: Page/Page column 35 ;
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 122, # 50 p. 12610 - 12611
  • Route3
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      21917-20-4
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    • In-stock
      Rac-(3ar,6as)-hexahydro-1h-cyclopenta[c]furan-1,3-dione, cis|CS-0215478
      35878-28-5

    References

    • US4206137 A1, ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅲ
Hazard Statements : H315-H318
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   0.4861
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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