Cas no 155320-76-6 (Cyclohexanone,2-methoxy-, (2S)-)

(2S)-2-Methoxycyclohexanone is a chiral cyclic ketone derivative characterized by a methoxy substituent at the 2-position of the cyclohexanone ring. Its stereospecific (S)-configuration makes it valuable in asymmetric synthesis and pharmaceutical intermediates, where enantioselectivity is critical. The compound’s structural features, including the electron-donating methoxy group, influence its reactivity in nucleophilic additions and reductions, offering controlled selectivity in synthetic pathways. It is commonly employed in the preparation of fine chemicals, catalysts, and chiral auxiliaries. High purity grades ensure consistency in research and industrial applications, particularly in stereocontrolled transformations. Proper handling under inert conditions is recommended due to potential sensitivity to oxidation.
Cyclohexanone,2-methoxy-, (2S)- structure
155320-76-6 structure
Product Name:Cyclohexanone,2-methoxy-, (2S)-
CAS No:155320-76-6
MF:C7H12O2
MW:128.168982505798
CID:106945
PubChem ID:642158
Update Time:2025-11-02

Cyclohexanone,2-methoxy-, (2S)- Chemical and Physical Properties

Names and Identifiers

    • Cyclohexanone,2-methoxy-, (2S)-
    • (S)-2- Methoxycyclohexanone
    • (2S)-2-methoxycyclohexanone
    • (2S)-methox
    • (S) 2-methoxycyclohexanone
    • (S)-(-)-2-methoxycyclohexanone
    • (S)-2-(methoxycarbonylmethyl)piperidine-1-carboxylic acid tert-butyl ester
    • (S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate
    • 1,1-dimethylethyl(2S)-2-[2-(methyloxy)-2-oxoethyl]-1-piperidinecarboxylate
    • AK-75680
    • ANW-60983
    • CTK8B8659
    • S-MON
    • (S)-2-METHOXYCYCLOHEXANONE
    • 155320-76-6
    • SCHEMBL1568359
    • (S)-2-Methoxycyclohexan-1-one
    • JYJURPHZXCLFDX-ZETCQYMHSA-N
    • (2S) -2-methoxycyclohexanone
    • AKOS006277471
    • A809634
    • Cyclohexanone, 2-methoxy-, (2S)-
    • (2S)-2-methoxycyclohexan-1-one
    • starbld0018316
    • MDL: MFCD02682988
    • Inchi: 1S/C7H12O2/c1-9-7-5-3-2-4-6(7)8/h7H,2-5H2,1H3/t7-/m0/s1
    • InChI Key: JYJURPHZXCLFDX-ZETCQYMHSA-N
    • SMILES: O(C)[C@@H]1C(CCCC1)=O

Computed Properties

  • Exact Mass: 128.08376
  • Monoisotopic Mass: 128.083729621g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 110
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.7
  • Topological Polar Surface Area: 26.3?2

Experimental Properties

  • PSA: 26.3

Cyclohexanone,2-methoxy-, (2S)- Pricemore >>

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Cyclohexanone,2-methoxy-, (2S)- Related Literature

  • 1. Synthesis of esters of the potent anti-bacterial trinems and analogues
    P. Mark Jackson,Stanley M. Roberts,Silvia Davalli,Daniele Donati,Carla Marchioro,Alcide Perboni,Stefano Proviera,Tino Rossi J. Chem. Soc. Perkin Trans. 1 1996 2029

Additional information on Cyclohexanone,2-methoxy-, (2S)-

Comprehensive Guide to Cyclohexanone,2-methoxy-, (2S)- (CAS No. 155320-76-6): Properties, Applications, and Market Insights

Cyclohexanone,2-methoxy-, (2S)- (CAS No. 155320-76-6) is a chiral organic compound with significant applications in pharmaceuticals, fragrances, and specialty chemicals. This optically active cyclohexanone derivative is characterized by its unique stereochemistry, making it valuable for asymmetric synthesis and enantioselective reactions. The compound's methoxy group at the 2-position enhances its reactivity and selectivity in various chemical transformations.

The growing demand for chiral building blocks in drug development has increased interest in (2S)-2-methoxycyclohexanone. Researchers are particularly focused on its role in synthesizing pharmaceutical intermediates, where its stereochemical purity can significantly influence drug efficacy. Recent studies highlight its potential in creating novel therapeutic agents for neurological disorders, leveraging its ability to cross the blood-brain barrier.

In the fragrance industry, Cyclohexanone,2-methoxy-, (2S)- serves as a precursor for sophisticated aroma compounds. Its structural features contribute to the creation of long-lasting floral and woody notes, making it popular in premium perfumery. The compound's stereospecificity allows perfumers to achieve precise scent profiles, addressing the market's demand for customized fragrance formulations.

From a synthetic chemistry perspective, 155320-76-6 demonstrates remarkable versatility. It participates in Michael additions, aldol condensations, and reductive aminations with high diastereoselectivity. These properties make it invaluable for constructing complex molecular architectures in medicinal chemistry. Recent advancements in continuous flow chemistry have improved the efficiency of its production, reducing costs and environmental impact.

The global market for chiral chemicals like (2S)-2-methoxycyclohexanone is projected to grow at 6.8% CAGR through 2030, driven by expanding pharmaceutical R&D. Asia-Pacific currently leads production, with increasing capacity in green chemistry facilities that emphasize sustainable manufacturing. Regulatory trends favoring enantiomerically pure drugs further boost demand for this high-purity intermediate.

Analytical characterization of Cyclohexanone,2-methoxy-, (2S)- typically involves chiral HPLC, optical rotation measurement, and NMR spectroscopy. These techniques ensure the compound meets stringent pharmaceutical-grade specifications. Storage recommendations include protection from light and moisture at controlled temperatures to maintain its stereochemical integrity over extended periods.

Emerging applications in agrochemicals and electronic materials present new opportunities for 155320-76-6. Its structural motifs show promise in developing chiral liquid crystals for display technologies and stereoselective pesticides with reduced environmental persistence. These developments align with current industry priorities for sustainable specialty chemicals.

For researchers working with (2S)-2-methoxycyclohexanone, proper handling procedures should be followed despite its non-hazardous classification. Standard laboratory precautions include using appropriate PPE and working in well-ventilated areas. The compound's low acute toxicity profile makes it suitable for various laboratory applications without requiring specialized containment.

Future research directions for Cyclohexanone,2-methoxy-, (2S)- include exploring its potential in biocatalysis and enzyme-mediated transformations. The integration of machine learning in reaction optimization may further enhance its synthetic utility. As the chemical industry moves toward digitalization and Industry 4.0, this compound's well-characterized properties position it as an ideal candidate for automated synthesis platforms.

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