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CS-W001157 4
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(3aR,6aR)-2,2-Dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

  • CAS No. 115509-13-2

  • Cat. No. CS-0038699
  • Purity≥98%
  • MDL No.None

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

(3aR,6aR)-2,2-Dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one|CS-0038699

Structure of 115509-13-2

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General Information

  • CAS No. 115509-13-2
  • Cat. No. CS-0038699
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀O₃
  • Molecular Weight 154.16
  • Synonym(s) None
  • SMILES CC1(C)O[C@@H]2C=CC(=O)[C@@H]2O1

Description

This cyclopentadienone derivative features a rigid, fused bicyclic framework with two methyl groups at the 2-position and a dioxolane ring, conferring enhanced stability and defined stereochemistry. The ketone functionality at C4 enables selective nucleophilic additions, while the overall structure supports efficient incorporation into complex molecular architectures under standard conditions.

Application

(3aR,6aR)-2,2-Dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one serves as a stable, bench-ready chiral synthon for the construction of complex carbocyclic and heterocyclic scaffolds. Its rigid cyclopentane core with defined stereochemistry enables predictable diastereoselective transformations, while the 1,3-dioxolane ring enhances functional group tolerance and facilitates downstream derivatization in medicinal chemistry campaigns.

Synthesis

  • Route1
    • 1,3-Dioxolane-4-methanol, α,5-diethenyl-2,2-dimethyl-, (4S,5R)-|CS-0039496
      683276-43-9
    • ~94%
    • In-stock
      (3aR,6aR)-2,2-Dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one|CS-0038699
      115509-13-2

    References

    • The Trustees of the University of Pennsylvania; Monell Chemical Sense Center Patent: US2009/76142 A1, 2009 ; Location in patent: Page/Page column 15 ;
  • Route2
    • null|null
      369647-25-6
    • ~92%
    • In-stock
      (3aR,6aR)-2,2-Dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one|CS-0038699
      115509-13-2

    References

    • UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC. Patent: WO2008/124157 A1, 2008 ; Location in patent: Page/Page column 20 ;
  • Route3
    • (3aS,4S,6aR)-2,2-Dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol|CS-0130979
      185622-63-3
    • ~90%
    • In-stock
      (3aR,6aR)-2,2-Dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one|CS-0038699
      115509-13-2

    References

    • Moon, Hyung Ryong; Choi, Won Jun; Kim, Hea Ok; Jeong, Lak Shin Tetrahedron Asymmetry, 2002 , vol. 13, # 11 p. 1189 - 1193

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
Precautionary Statements : P261-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   35.53
  • LogP   0.6454
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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