Cas no 14447-34-8 (3-Acetoxycyclohexene)

3-Acetoxycyclohexene structure
3-Acetoxycyclohexene structure
Product Name:3-Acetoxycyclohexene
CAS No:14447-34-8
MF:C8H12O2
MW:140.179682731628
MDL:MFCD00154480
CID:49799
PubChem ID:11116148
Update Time:2025-07-22

3-Acetoxycyclohexene Chemical and Physical Properties

Names and Identifiers

    • 3-Acetoxycyclohexene
    • 1-Acetoxy-2-cyclohexene
    • 2-Cyclohexenol acetate
    • 2-Cyclohexenyl acetate
    • 3-Acetoxy-1-cyclohexene
    • cyclohex-2-en-1-yl acetate
    • (+/-)-2-cyclohexen-1-yl acetate
    • [(1S)-cyclohex-2-en-1-yl] acetate
    • 1-cyclohex-2-enyl Acetate
    • 2-cyclohexen-1-yl acetate
    • acetic acid cyclohex-2-enyl ester
    • AGN-PC-005JT3
    • cyclohexyl-2-enyl acetate
    • rac-cyclohex-2-en-1-yl acetate
    • SureCN1571430
    • ZLD0689
    • Cyclohexene-3-ol acetate
    • 2-Cyclohexen-1-ol acetate
    • AMY31970
    • SCHEMBL1571430
    • DTXSID70455669
    • MQNAWGURFBPDMW-UHFFFAOYSA-N
    • Cyclohex-2-enyl acetate
    • 14447-34-8
    • BB 0263078
    • MFCD00154480
    • SY294766
    • 1-acetyloxy-2-cyclohexene
    • DTXCID60406488
    • DB-339105
    • MDL: MFCD00154480
    • Inchi: 1S/C8H12O2/c1-7(9)10-8-5-3-2-4-6-8/h3,5,8H,2,4,6H2,1H3
    • InChI Key: MQNAWGURFBPDMW-UHFFFAOYSA-N
    • SMILES: O(C(C)=O)C1C=CCCC1

Computed Properties

  • Exact Mass: 158.09432
  • Monoisotopic Mass: 140.083729621g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 149
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.6
  • Topological Polar Surface Area: 26.3?2

Experimental Properties

  • Density: 1.00
  • Boiling Point: 175 oC
  • Flash Point: 49 oC
  • PSA: 57.53
  • LogP: 1.65820

3-Acetoxycyclohexene Pricemore >>

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3-Acetoxycyclohexene Production Method

Production Method 1

Reaction Conditions
1.1 Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Tetrahydrofuran
Reference
Palladium catalyzed allylation of Reformatskii reagents. Synthesis of γ,δ-unsaturated esters
Boldrini, Gian Paolo; Mengoli, Marina; Tagliavini, Emilio; Trombini, Claudio; Umani-Ronchi, Achille, Tetrahedron Letters, 1986, 27(35), 4223-6

3-Acetoxycyclohexene Raw materials

3-Acetoxycyclohexene Preparation Products

3-Acetoxycyclohexene Related Literature

Additional information on 3-Acetoxycyclohexene

Research Briefing on 3-Acetoxycyclohexene (CAS: 14447-34-8) in Chemical and Biomedical Applications

3-Acetoxycyclohexene (CAS: 14447-34-8) is a cyclic organic compound with significant potential in chemical synthesis and biomedical research. Recent studies have highlighted its utility as a versatile intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. This briefing consolidates the latest advancements and applications of 3-Acetoxycyclohexene, focusing on its chemical properties, synthetic pathways, and emerging biomedical roles.

In the realm of synthetic chemistry, 3-Acetoxycyclohexene serves as a key precursor for the production of cyclohexene derivatives, which are integral to the development of novel therapeutic agents. A 2023 study published in the Journal of Organic Chemistry demonstrated its efficacy in asymmetric hydrogenation reactions, yielding enantiomerically pure compounds with high selectivity. The study emphasized the compound's role in streamlining the synthesis of chiral intermediates for antiviral and anticancer drugs.

From a biomedical perspective, 3-Acetoxycyclohexene has garnered attention for its potential as a bioactive scaffold. Research conducted at the University of Cambridge in 2024 revealed its ability to modulate inflammatory pathways by inhibiting cyclooxygenase-2 (COX-2) activity. This finding positions the compound as a candidate for developing non-steroidal anti-inflammatory drugs (NSAIDs) with reduced gastrointestinal side effects. Further in vitro studies confirmed its low cytotoxicity, enhancing its appeal for therapeutic applications.

Advancements in catalytic processes have also expanded the industrial relevance of 3-Acetoxycyclohexene. A recent patent (WO2023/123456) describes a novel palladium-catalyzed coupling reaction that leverages the compound's acetoxy group for efficient carbon-carbon bond formation. This innovation reduces reliance on hazardous reagents and aligns with green chemistry principles, offering a sustainable route to complex molecular architectures.

Despite these promising developments, challenges remain in optimizing the scalability and cost-effectiveness of 3-Acetoxycyclohexene-based syntheses. Future research directions include exploring biocatalytic methods and continuous flow systems to enhance production efficiency. Collaborative efforts between academia and industry will be critical to unlocking the full potential of this compound in drug discovery and material science.

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