Cas no 102282-10-0 ((2R)-2-4-(benzyloxy)phenyloxirane)

(2R)-2-[4-(Benzyloxy)phenyl]oxirane is a chiral epoxide derivative characterized by its stereospecific (R)-configuration at the oxirane ring. This compound serves as a valuable synthetic intermediate in organic and medicinal chemistry, particularly for the construction of enantiomerically pure pharmaceuticals or bioactive molecules. The benzyloxy group enhances solubility in organic solvents, facilitating downstream functionalization. Its rigid oxirane ring offers reactivity for nucleophilic ring-opening reactions, enabling selective modifications at the benzylic or phenyl positions. The compound’s defined stereochemistry ensures precise control over asymmetric synthesis pathways. Suitable for use in catalytic transformations or as a precursor for chiral ligands, it is typically handled under inert conditions due to its epoxide sensitivity.
(2R)-2-4-(benzyloxy)phenyloxirane structure
102282-10-0 structure
Product Name:(2R)-2-4-(benzyloxy)phenyloxirane
CAS No:102282-10-0
MF:C15H14O2
MW:226.270464420319
CID:1135252
PubChem ID:11379137
Update Time:2025-06-12

(2R)-2-4-(benzyloxy)phenyloxirane Chemical and Physical Properties

Names and Identifiers

    • Oxirane, [4-(phenylmethoxy)phenyl]-, (R)-
    • (R)-2-(4-benzyloxyphenyl)oxirane
    • (2R)-2-4-(benzyloxy)phenyloxirane
    • AKOS021414898
    • 102282-10-0
    • KTFPWENWGCSNHE-HNNXBMFYSA-N
    • (2R)-2-[4-(benzyloxy)phenyl]oxirane
    • SCHEMBL8483583
    • EN300-1864343
    • Inchi: 1S/C15H14O2/c1-2-4-12(5-3-1)10-16-14-8-6-13(7-9-14)15-11-17-15/h1-9,15H,10-11H2/t15-/m0/s1
    • InChI Key: KTFPWENWGCSNHE-HNNXBMFYSA-N
    • SMILES: O1C[C@H]1C1C=CC(=CC=1)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 226.09942
  • Monoisotopic Mass: 226.099379685g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 4
  • Complexity: 227
  • 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: 2.7
  • Topological Polar Surface Area: 21.8?2

Experimental Properties

  • PSA: 21.76
  • LogP: 3.33690

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Additional information on (2R)-2-4-(benzyloxy)phenyloxirane

Comprehensive Overview of (2R)-2-4-(benzyloxy)phenyloxirane (CAS No. 102282-10-0)

(2R)-2-4-(benzyloxy)phenyloxirane (CAS No. 102282-10-0) is a chiral epoxide compound with significant applications in pharmaceutical and organic synthesis. Its unique structure, featuring a benzyloxy group attached to a phenyloxirane ring, makes it a valuable intermediate in the production of bioactive molecules. Researchers and industry professionals frequently search for this compound due to its role in asymmetric synthesis and drug development, particularly in the context of chiral building blocks and epoxide ring-opening reactions.

The compound's stereochemistry, denoted by the (2R) configuration, is critical for its reactivity and selectivity in synthetic pathways. Recent trends in green chemistry and sustainable synthesis have heightened interest in such chiral epoxides, as they enable efficient routes to complex molecules with minimal waste. Questions like "How to synthesize (2R)-2-4-(benzyloxy)phenyloxirane?" or "What are the applications of CAS 102282-10-0 in drug discovery?" are commonly explored in academic and industrial forums.

From a technical perspective, (2R)-2-4-(benzyloxy)phenyloxirane is often utilized in the preparation of pharmaceutical intermediates, such as beta-blockers or antifungal agents. Its epoxide ring is highly reactive, allowing for nucleophilic attack by amines, alcohols, or other nucleophiles to form diversified derivatives. This property aligns with the growing demand for custom synthesis and tailor-made molecules in the life sciences sector.

In addition to its synthetic utility, the compound has garnered attention in catalysis research. For instance, its use in enantioselective catalysis has been explored to achieve high yields and optical purity in target products. Searches related to "CAS 102282-10-0 catalytic applications" or "chiral epoxide derivatives" reflect this niche yet expanding area of interest.

Safety and handling of (2R)-2-4-(benzyloxy)phenyloxirane are also frequently discussed topics. While not classified as hazardous, proper storage conditions (e.g., under inert atmosphere) are recommended to maintain its stability. Queries such as "Is CAS 102282-10-0 stable at room temperature?" or "How to store chiral epoxides?" are common among laboratory professionals.

Looking ahead, the compound's relevance is expected to grow alongside advancements in precision medicine and biocatalysis. Its role in creating enantiomerically pure drugs—a key focus in modern therapeutics—underscores its importance. As the industry shifts toward high-value intermediates, (2R)-2-4-(benzyloxy)phenyloxirane will likely remain a cornerstone in synthetic chemistry.

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