3-Oxabicyclo[3.2.0]heptane-2,4-dione

Name: 3-Oxabicyclo[3.2.0]heptane-2,4-dione
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 4462-96-8
Cat. No. CS-0051229
Purity≥98%
MDL No.MFCD00799396

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3-Oxabicyclo[3.2.0]heptane-2,4-dione|CS-0051229

Structure of 4462-96-8

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General Information

CAS No. 4462-96-8
Cat. No. CS-0051229
Purity ≥98%
MDL No. MFCD00799396
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₆O₃
Molecular Weight 126.11
Synonym(s) 1,2-Cyclobutanedicarboxylic anhydride, cis-,
SMILES O=C1OC(=O)C2CCC12

Description

3-Oxabicyclo[3.2.0]heptane-2,4-dione is a strained bicyclic diketone featuring a fused oxabicycle core with adjacent carbonyl groups. This rigid framework imparts high reactivity in cycloaddition and rearrangement reactions, enabling efficient access to complex carbocyclic architectures. The molecule’s electron-deficient nature facilitates nucleophilic attack at the C2 position, while the bridged structure enhances regioselectivity in synthetic transformations.

Application

3-Oxabicyclo[3.2.0]heptane-2,4-dione serves as a versatile bicyclic synthon in synthetic organic chemistry, enabling efficient access to strained carbocyclic frameworks. Its diketone functionality supports selective reductions, nucleophilic additions, and cyclization cascades, while the bridged oxo moiety enhances structural rigidity. The compound exhibits bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows and the construction of complex polycyclic systems.

Synthesis

Route1
- 108-31-6
- 54509-73-8
- ~72%
- In-stock
  
  4462-96-8
References
- Faure, Sophie; Jensen, Anders A.; Maurat, Vincent; Gu, Xin; Sagot, Emmanuelle; Aitken, David J.; Bolte, Jean; Gefflaut, Thierry; Bunch, Lennart Journal of Medicinal Chemistry, 2006 , vol. 49, # 22 p. 6532 - 6538
Route2
- 10374-07-9
- ~98%
- In-stock
  
  4462-96-8
References
- Tufariello, Joseph J.; Milowsky, Arnold S.; Al-Nuri, Mohammed; Goldstein, Steven Tetrahedron Letters, 1987 , vol. 28, # 3 p. 267 - 270
Route3
- 2144-31-2
- ~%
- In-stock
  
  4462-96-8
References
- Buchman et al. Journal of the American Chemical Society, 1942 , vol. 64, p. 2696,2697

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 43.37
LogP 0.096
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Tetrahydrofuran compounds

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Key Words

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3-Oxabicyclo[3.2.0]heptane-2,4-dione

CAS No. 4462-96-8

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